Abstract
The key advances in oligo- or polymerization of olefins catalyzed by the 2,6-bis(imino)pyridine-based iron and cobalt complexes were presented. Particular attention was paid to trace the structural evolution of the 2,6-bis(imino)pyridine and related ligands, recent understandings of the relationship between catalyst structure and catalytic activity, and applications of iron and cobalt catalysts in oligo- or polymerization of olefins. Additionally, the mechanistic aspects of the oligo- or polymerization reactions, involving catalyst activation, oligo- or polymerization initiation, chain propagation and chain transfer, activators or cocatalysts, monomers and comonomers, and immobilization of iron and cobalt catalysts, have also been reviewed and discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- AIBN:
-
Azobis-iso-butyronitrile
- ATRP:
-
Atom transfer radical polymerization
- BIP:
-
2,6-Bis(imino)pyridine
- BTCA:
-
Benzene-1,3,5-tricarboxylic acid
- Bz:
-
Benzyl
- 13C NMR:
-
Carbon-13 nuclear magnetic resonance spectroscopy
- CGC:
-
Constrained geometry catalysts
- CRYSTAF:
-
Crystallization analysis fractionation
- DFT:
-
Density functional theory
- DSC:
-
Differential scanning calorimetry
- EPR:
-
Electron paramagnetic resonance spectroscopy
- ESI-MS:
-
Electrospray ionization mass spectrometry
- EVE:
-
Ethyl vinyl ether
- GPC/SEC:
-
Gel permeation chromatography/size-exclusion chromatography
- 1H NMR:
-
Proton nuclear magnetic resonance spectroscopy
- i-BVE:
-
iso-Butyl vinyl ether
- LDA:
-
Lithium diisopropylamide
- LLDPE:
-
Linear low-density polyethylene
- MA:
-
Methyl acrylate
- MAO:
-
Methylaluminoxane
- MM:
-
Molecular mechanics
- MMA:
-
Methyl methacrylate
- MMAO:
-
Modified methylaluminoxane
- Mn :
-
Number-average molecular weight
- Mw :
-
Weight-average molecular weight
- Mw/Mn :
-
Polydispersity index
- n-BMA:
-
n-Butyl methacrylate
- n-BVE:
-
n-Butyl vinyl ether
- NMR:
-
Nuclear magnetic resonance spectroscopy
- OTf:
-
Triflate group (trifluoromethanesulfonate, CF3SO3 ?)
- OTs:
-
Tosylate group (p-toluenesulfonate, p-CH3C6H4SO3 ?)
- PE:
-
Polyethylene
- PES:
-
Potential energy surface
- PMAO:
-
Polymeric methylaluminoxane
- PP:
-
Polypropylene
- PS:
-
Polystyrene
- QM:
-
Quantum mechanics
- SAXS:
-
Small-angle X-ray scattering
- SGEF:
-
Solvent gradient elution fractionation
- SHOP:
-
Shell higher olefin process
- t-BA:
-
tert-Butyl acrylate
- t-BMA:
-
tert-Butyl methacrylate
- TEAO:
-
Tetraethylaluminoxane
- WAXD:
-
Wide-angle X-ray diffraction
- XPS:
-
X-ray photoelectron spectroscopy
References
Sinn H, Kaminsky W, Vollmer HJ, Woldt R (1980) Living polymers on polymerization with extremely productive Ziegler catalysts. Angew Chem Int Ed 19:390–392
Sinn H, Kaminsky W (1980) Ziegler-Natta catalysis. Adv Organomet Chem 18:99–149
Farina M, Silvestro GD, Sozzani P (1993) Hemiisotactic polypropylene: a key point in the elucidation of the polymerization mechanism with metallocene catalysts. Macromolecules 26:946–950
Coates GW, Waymouth RM (1995) Oscillating stereocontrol: a strategy for the synthesis of thermoplastic elastomeric polypropylene. Science 267:217–219
Hauptman E, Waymouth RM, Ziller JW (1995) Stereoblock polypropylene: ligand effects on the stereospecificity of 2-arylindene zirconocene catalysts. J Am Chem Soc 117:11586–11587
Smith JA, Brintzinger HH (1981) Ansa-metallocene derivatives 3. Influence of an interannular ethylene bridge on the reactivity of titanocene derivatives. J Organomet Chem 218:159–167
Wild FRWP, Zsolnal L, Huttner G, Brintzinger HH (1982) Ansa-metallocene derivatives 4. Synthesis and molecular structures of chiral ansa-titanocene derivatives with bridge tetrahydroindenyl ligands. J Organomet Chem 232:233–247
Ewen JA (1984) Mechanisms of stereochemical control in propylene polymerizations with soluble Group 4B metallocene/methylalumoxane cata1ysts. J Am Chem Soc 106:6355–6364
Ewen JA, Jones RL, Razavi A, Ferrara JD (1988) Syndiospecific propylene polymerizations with Group 4 metallocenes. J Am Chem Soc 110:6255–6256
Canich JAM (Exxon Chemical Patents, Inc.) (1991) Process for producing crystalline poly-alpha-olefins with a monocyclopentadienyl transition metal catalyst system. US Patent 5026798
Canich JAM, Licciardi GF (Exxon Chemical Patents, Inc.) (1991) Mono-Cp heteroatom containing group IVB transition metal complexes with MAO: supported catalyst for olefin polymerization. US Patent 5057475
Canich JAM (Exxon Chemical Patents, Inc.) (1991) Olefin polymerization catalysts. Eur. Patent 0420436
Johnson LK, Killian CM, Brookhart M (1995) New Pd(II)- and Ni(II)-based catalysts for polymerization of ethylene and ?-olefins. J Am Chem Soc 117:6414–6415
Small BL, Brookhart M, Bennett AMA (1998) Highly active iron and cobalt catalysts for the polymerization of ethylene. J Am Chem Soc 120:4049–4050
Small BL, Brookhart M (1998) Iron-based catalysts with exceptionally high activities and selectivities for oligomerization of ethylene to linear ?-olefins. J Am Chem Soc 120:7143–7144
Britovsek GJP, Gibson VC, Kimberley BS, Maddox PJ, McTavish SJ, Solan GA, White AJP, Williams DJ (1998) Novel olefin polymerization catalysts based on iron and cobalt. Chem Commun 849–850
Fujita T, Tohi Y, Mitani M, Matsui S, Saito J, Nitabaru M, Sugi K, Makio H, Tsutsui T (Mitsui Chemicals, Inc.) (1998) Olefin polymerization catalysts, transition metal compounds, processes for olefin polymerization, and alpha-olefin/conjugated diene copolymers. Eur Patent 0874005
Wang C, Friedrich S, Younkin TR, Li RT, Grubbs RH, Bansleben DA, Day MW (1998) Neutral nickel(II)-based catalysts for ethylene polymerization. Organometallics 17:3149–3151
Mitani M, Mohri J, Yoshida Y, Saito J, Ishii S, Tsuru K, Matsui S, Furuyama R, Nakano T, Tanaka H, Kojoh S, Matsugi T, Kashiwa N, Fujita T (2002) Living polymerization of ethylene catalyzed by titanium complexes having fluorine-containing phenoxy-imine chelate ligands. J Am Chem Soc 124:3327–3336
Mitani M, Furuyama R, Mohri J, Saito J, Ishii S, Terao H, Nakano T, Tanaka H, Fujita T (2003) Syndiospecific living propylene polymerization catalyzed by titanium complexes having fluorine-containing phenoxy-imine chelate ligands. J Am Chem Soc 125:4293–4305
Mitani M, Nakano T, Fujita T (2003) Unprecedented living olefin polymerization derived from an attractive interaction between a ligand and a growing polymer chain. Chem Eur J 9:2396–2403
Bianchini C, Giambastiani G, Rios IG, Mantovani G, Meli A, Segarra AM (2006) Ethylene oligomerization, homopolymerization and copolymerization by iron and cobalt catalysts with 2, 6-(bis-organylimino)pyridyl ligands. Coord Chem Rev 250:1391–1418
Gibson VC, Redshaw C, Solan GA (2007) Bis(imino)pyridines: surprisingly reactive ligands and a gateway to new families of catalysts. Chem Rev 107:1745–1776
Bianchini C, Giambastiani G, Luconi L, Meli A (2010) Olefin oligomerization, homopolymerization and copolymerization by late transition metals supported by (imino)pyridine ligands. Coord Chem Rev 254:431–455
Calderazzo F, Englert U, Pampaloni G, Santi R, Sommazzi A, Zinna M (2005) Bis(arylimino)pyridine derivatives of Group 4 metals: preparation, characterization and activity in ethylene polymerization. Dalton Trans 914–922
Reardon D, Conan F, Gambarotta S, Yap G, Wang Q (1999) Life and death of an active ethylene polymerization catalyst. Ligand involvement in catalyst activation and deactivation. Isolation and characterization of two unprecedented neutral and anionic vanadium(I) alkyls. J Am Chem Soc 121:9318–9325
Colamarco E, Milione S, Cuomo C, Grassi A (2004) Homo- and copolymerization of butadiene catalyzed by an bis(imino)pyridyl vanadium complex. Macromol Rapid Commun 25:450–454
Schmidt R, Welch MB, Knudsen RD, Gottfried S, Alt HG (2004) N,N,N-Tridentate iron(II) and vanadium(III) complexes Part I. Synthesis and characterization. J Mol Catal A: Chem 222:9–15
Schmidt R, Welch MB, Knudsen RD, Gottfried S, Alt HG (2004) N,N,N-Tridentate iron(II) and vanadium(III) complexes Part II: catalytic behavior for the oligomerization and polymerization of ethene and characterization of the resulting products. J Mol Catal A Chem 222:17–25
Schmidt R, Das PK, Welch MR, Knudsen RD (2004) N, N, N-Tridentate iron(II) and vanadium(III) complexes Part III. UV–vis spectroscopic studies of reactions of ethene-oligomerization and polymerization catalysts with methyl aluminoxane cocatalyst. J Mol Catal A Chem 222:27–45
Hanton MJ, Tenza K (2008) Bis(imino)pyridine complexes of the first-row transition metals: alternative methods of activation. Organometallics 27:5712–5716
Semikolenova NV, Zakharov VA, Echevskaja LG, Matsko MA, Bryliakov KP, Talsi EP (2009) Homogeneous catalysts for ethylene polymerization based on bis(imino)pyridine complexes of iron, cobalt, vanadium and chromium. Catal Today 144:334–340
Romero J, Carrillo-Hermosilla F, Antiñolo A, Otero A (2009) Homogeneous and supported bis(imino)pyridyl vanadium(III) catalysts. J Mol Catal A Chem 304:180–186
Esteruelas MA, López AM, Méndez L, Oliván M, Oñate E (2003) Preparation, structure, and ethylene polymerization behavior of bis(imino)pyridyl chromium(III) complexes. Organometallics 22:395–406
Small BL, Carney MJ, Holman DM, O’Rourke CE, Halfen JA (2004) New chromium complexes for ethylene oligomerization: Extended use of tridentate ligands in metal-catalyzed olefin polymerization. Macromolecules 37:4375–4386
Nakayama Y, Sogo K, Yasuda H, Shiono T (2005) Unique catalytic behavior of chromium complexes having halogenated bis(imino)pyridine ligands for ethylene polymerization. J Polym Sci Part A: Polym Chem 43:3368–3375
Chen J, Huang Y, Li Z, Zhang Z, Wei C, Lan T, Zhang W (2006) Syntheses of iron, cobalt, chromium, copper and zinc complexes with bulky bis(imino)pyridyl ligands and their catalytic behaviors in ethylene polymerization and vinyl polymerization of norbornene. J Mol Catal A: Chem 259:133–141
Vidyaratne I, Scott J, Gambarotta S, Duchateau R (2007) Reactivity of chromium complexes of a bis(imino)pyridine ligand: highly active ethylene polymerization catalysts carrying the metal in a formally low oxidation state. Organometallics 26:3201–3211
Hiya K, Nakayama Y, Yasuda H (2003) Facile syntheses of bis[1-(arylimino)ethyl]pyridine-MoCl3/MMAO catalytic systems and their dual catalytic functions for ROMP of norbornene and linear polymerization of ethylene. Macromolecules 36:7916–7922
Suzuki H, Matsumura S, Satoh Y, Sogoh K, Yasuda H (2004) Random copolymerizations of norbornene with other monomers catalyzed by novel Ni compounds involving N- or O-donated ligands. React Funct Polym 58:77–91
Suzuki H, Matsumura S, Satoh Y, Sogoh K, Yasuda H (2004) Random and block copolymerizations of norbornene with conjugated 1, 3-dienes catalyzed by novel Ni compounds involving N- or O-donated ligands. React Funct Polym 59:253–266
Su B, Zhao J, Zhang Q, Qin W (2009) Cobalt(II) and nickel(II) complexes bearing mono(imino)pyridyl and bis(imino)pyridyl ligands: preparation, structure and ethylene polymerization/oligomerization behaviors. Polym Int 58:1051–1057
Knijnenburg Q, Gambarotta S, Budzelaar PHM (2006) Ligand-centred reactivity in diiminepyridine complexes. Dalton Trans 5442–5448
Mecking S (2001) Olefin polymerization by late transition metal complexes-A root of Ziegler catalysts gains new ground. Angew Chem Int Ed 40:534–540
Keim W, Kowaldt FH, Goddard R, Kruger C (1978) Novel coordination of (benzoylmethylene)triphenylphosphorane in a nickel oligomerization catalyst. Angew Chem Int Ed 17:466–467
Peuckert M, Keim W (1983) A new nickel-complex for the oligomerization of ethylene. Organometallics 2:594–597
Lions F, Martin KV (1957) Tridentate chelate compounds. I. J Am Chem Soc 79:2733–2738
Figgins PE, Busch DH (1960) Complexes of iron(II), cobalt(II) and nickel(II) with biacetyl-bis-methylimine, 2-pyridinal-methylimine and 2, 6-pyridindial-bis-methylimine. J Am Chem Soc 82:820–824
Figgins PE, Busch DH (1961) Infrared spectra of octahedral complexes of iron(II), cobalt(II) and nickel (II) with biacetyl-bis-methylimine and pyridinal methylamines. J Phys Chem 65:2236–2240
Restivo RJ, Ferguson G (1976) Structural characterization of metal-complexes of 2,6-diacetylpyridine-bis(imines)-crystal and molecular-structure of dinitrato[2,6-bis[1-(phenylimino)ethyl]pyridine]copper(II). Dalton Trans 518–521
Small BL, Brookhart M (1999) Polymerization of propylene by a new generation of iron catalysts: mechanisms of chain initiation, propagation, and termination. Macromolecules 32:2120–2130
Bristovsek GJP, Mastroianni S, Solan GA, Baugh SPD, Redshaw C, Gibson VC, White AJP, Williams DJ, Elsegood MRJ (2000) Oligomerisation of ethylene by bis(imino)pyridyliron and -cobalt complexes. Chem Eur J 6:2221–2231
Britovsek GJP, Bruce M, Gibson VC, Kimberley BS, Maddox PJ, Mastroianni S, McTavish SJ, Redshaw C, Solan GA, Strömberg S, White AJP, Williams DJ (1999) Iron and cobalt ethylene polymerization catalysts bearing 2, 6-bis(imino)pyridyl ligands: synthesis, structures, and polymerization studies. J Am Chem Soc 121:8728–8740
Wang J, Li W, Jiang B, Yang Y (2009) Fe(acac)n and Co(acac)n bearing different bis(imino)pyridine ligands for ethylene polymerization and oligomerization. J Appl Polym Sci 113:2378–2391
Bluhm ME, Folli C, Döring M (2004) New iron-based bis(imino)pyridine and acetyliminopyridine complexes as single-site catalysts for the oligomerization of ethylene. J Mol Catal A Chem 212:13–18
Cámpora J, Cartes MÁ, Rodríguez-Delgado A, Naz AM, Palma P, Pérez CM (2009) Studies on the atropisomerism of Fe(II) 2, 6-bis(N-arylimino)pyridine complexes. Inorg Chem 48:3679–3691
Görl C, Alt HG (2007) Influence of the para-substitution in bis(arylimino)pyridine iron complexes on the catalytic oligomerization and polymerization of ethylene. J Organomet Chem 692:4580–4592
Abu-Surrah AS, Lappalainen K, Piironen U, Lehmus P, Repo T, Leskelä M (2002) New bis(imino)pyridine-iron(II)- and cobalt(II)-based catalysts: synthesis, characterization and activity toward polymerization of ethylene. J Organomet Chem 648:55–61
Schmidt R, Welch MB, Palackal SJ, Alt HG (2002) Heterogenized iron(II) complexes as highly active ethene polymerization catalysts. J Mol Catal A Chem 179:155–173
Chen Y, Chen R, Qian C, Dong X, Sun J (2003) Halogen-substituted 2, 6-bis(imino)pyridyl iron and cobalt complexes: highly active catalysts for polymerization and oligomerization of ethylene. Organometallics 22:4312–4321
Castro PM, Lappalainen K, Ahalgrén M, Leskelä M, Repo T (2003) Iron-based catalysts bearing bis(imido)-pyridine ligands for the polymerization of tert-butyl acrylate. J Polym Sci Part A Polym Chem 41:1380–1389
Long Z, Wua B, Yang P, Li G, Liu Y, Yang X-J (2009) Synthesis and characterization of para-nitro substituted 2, 6-bis(phenylimino) pyridyl Fe(II) and Co(II) complexes and their ethylene polymerization properties. J Organomet Chem 694:3793–3799
Chen Y, Qian C, Sun J (2003) Fluoro-substituted 2, 6-bis(imino)pyridyl iron and cobalt complexes: high-activity ethylene oligomerization catalysts. Organometallics 22:1231–1236
Kleigrewe N, Steffen W, Blömker T, Kehr G, Fröhlich R, Wibbeling B, Erker G, Wasilke J-C, Wu G, Bazan GC (2005) Chelate bis(imino)pyridine cobalt complexes: synthesis, reduction, and evidence for the generation of ethane polymerization catalysts by Li+ cation activation. J Am Chem Soc 127:13955–13968
Jurca T, Dawson K, Mallov I, Burchell T, Yap GPA, Richeson DS (2010) Disproportionation and radical formation in the coordination of “GaI” with bis(imino)pyridines. Dalton Trans 39:1266–1272
McTavish S, Britovsek GJP, Smit TM, Gibson VC, White AJP, Williams DJ (2007) Iron-based ethylene polymerization catalysts supported by bis(imino)pyridine ligands: derivatization via deprotonation/alkylation at the ketimine methyl position. J Mol Catal A Chem 261:293–300
Steves JE, Kennedy MD, Chiang KP, Kassel WS, Dougherty WG, Dudley TJ, Zubris DL (2009) Synthesis of a bulky bis(imino)pyridine compound: a methodology for systematic variation of steric bulk and energetic implications for metalation. Dalton Trans 1214–1222
Smit TM, Tomov AK, Gibson VC, White AJP, Williams DJ (2004) Dramatic effect of heteroatom backbone substituents on the ethylene polymerization behavior of bis(imino)pyridine iron catalysts. Inorg Chem 43:6511–6512
Ionkin AS, Marshall WJ, Adelman DJ, Fones BB, Fish BM, Schiffhauer MF (2006) High-temperature catalysts for the production of ?-olefins based on iron(II) and iron(III) tridentate bis(imino)pyridine complexes with double pattern of substitution: ortho-methyl plus meta-aryl. Organometallics 25:2978–2992
Gibson VC, Long NJ, Oxford PJ, White AJP, Williams DJ (2006) Ferrocene-substituted bis(imino)pyridine iron and cobalt complexes: toward redox-active catalysts for the polymerization of ethylene. Organometallics 25:1932–1939
Gong D, Wang B, Bai C, Bi J, Wang F, Dong W, Zhang X, Jiang L (2009) Metal dependent control of cis-/trans-1, 4 regioselectivity in 1, 3-butadiene polymerization catalyzed by transition metal complexes supported by 2, 6-bis[1-(iminophenyl)ethyl]pyridine. Polymer 50:6259–6264
Zhang Z, Zou J, Cui N, Ke Y, Hu Y (2004) Ethylene oligomerization catalyzed by a novel iron complex containing fluoro and methyl substituents. J Mol Catal A Chem 219:249–254
Archer AM, Bouwkamp MW, Cortez M, Lobkovsky E, Chirik PJ (2006) Arene coordination in bis(imino)pyridine iron complexes: identification of catalyst deactivation pathways in iron-catalyzed hydrogenation and hydrosilation. Organometallics 25:4269–4278
Tellmann KP, Gibson VC, White AJP, Williams DJ (2005) Selective dimerization/oligomerization of ?-olefins by cobalt bis(imino)pyridine catalysts stabilized by trifluoromethyl substituents: Group 9 metal catalysts with productivities matching those of iron systems. Organometallics 24:280–286
Ionkin AS, Marshall WJ, Adelman DJ, Fones BB, Fish BM, Scheffhauer MF, Soper PD, Waterland RL, Spence RE, Xie T (2008) High-temperature catalysts for the production of ?-olefins based on iron(II) and iron(III) tridentate bis(imino)pyridine complexes modified by nitrilo group. J Polym Sci Part A Polym Chem 46:585–611
Ionkin AS, Marshall WJ, Adelman DJ, Shoe AL, Spence RE, Xie T (2006) Nitro-substituted iron(II) tridentate bis(imino)pyridine complexes as high-temperature catalysts for the production of ?-olefins. J Polym Sci Part A Polym Chem 44:2615–2635
Ionkin AS, Marshall WJ, Adelman DJ, Fones BB, Fish BM, Schiffhauer MF (2008) High-temperature catalysts for the production of ?-olefins based on iron(II) and cobalt(II) tridentate bis(imino)pyridine complexes with a double pattern of substitution: o-methyl plus o-fluorine in the same imino arm. Organometallics 27:1147–1156
Kaul FAR, Puchta GT, Frey GD, Herdtweck E, Herrmann WA (2007) Iminopyridine complexes of 3d metals for ethylene polymerization: comparative structural studies and ligand size controlled chain termination. Organometallics 26:988–999
Bryliakov KP, Semikolenova NV, Zudin VN, Zakharov VA, Talsi EP (2004) Ferrous rather than ferric species are the active sites in bis(imino)pyridine iron ethylene polymerization catalysts. Catal Commun 5:45–48
Britovsek GJP, Clentsmith GKB, Gibson VC, Goodgame DML, McTavish SJ, Pankhurst QA (2002) The nature of the active site in bis(imino)pyridine iron ethylene polymerisation catalysts. Catal Commun 3:207–211
Martínez J, Cruz V, Ramos J, Gutiérrez-Oliva S, Martínez-Salazar J, Toro-Labbe A (2008) On the nature of the active site in bis(imino)pyridyl iron, a catalyst for olefin polymerization. J Phys Chem C 112:5023–5028
Cruz VL, Ramos J, Martínez-Salazar J, Gutiérrez-Oliva S, Toro-Labbé A (2009) Theoretical study on a multicenter model based on different metal oxidation states for the bis(imino)pyridine iron catalysts in ethylene polymerization. Organometallics 28:5889–5895
Raucoules R, Bruin T, Raybaud P, Adamo C (2008) Evidence for the iron(III) oxidation state in bis(imino)pyridine catalysts. A density functional theory study. Organometallics 27:3368–3377
Souane R, Isel F, Peruch F, Lutz PJ (2002) Pyridine bis(imine) cobalt or iron complexes for ethylene and 1-hexene (co)polymerization. C R Chim 5:43–48
Small BL, Marcucci AJ (2001) Iron catalysts for the head-to-head dimerization of ?-olefins and mechanistic implications for the production of linear ?-olefins. Organometallics 20:5738–5744
Babik ST, Fink G (2002) Propylene polymerization with a bisiminepyridine iron complex: activation with Ph3C[B(C6F5)4] and AlR3; iron hydride species in the catalytic cycle. J Mol Catal A Chem 188:245–253
Babik ST, Fink G (2003) Propylene bulk phase oligomerization with bisiminepyridine iron complexes in a calorimeter: mechanistic investigation of 1,2 versus 2,1 propylene insertion. J Organomet Chem 683:209–219
Pellecchia C, Mazzeo M, Pappalardo D (1998) Isotactic-specific polymerization of propene with an iron-based catalyst: polymer end groups and regiochemistry of propagation. Macromol Rapid Commun 19:651–655
Raucoules R, Bruin T, Raybaud P, Adamo C (2009) Theoretical unraveling of selective 1-butene oligomerization catalyzed by iron-bis(arylimino)pyridine. Organometallics 28:5358–5367
Small BL (2003) Tridentate cobalt catalysts for linear dimerization and isomerization of ?-olefins. Organometallics 22:3178–3183
Pelascini F, Peruch F, Lutz PJ, Wesolek M, Kress J (2005) Pyridine bis(imino) iron and cobalt complexes for ethylene polymerization: influence of the aryl imino substituents. Eur Polym J 41:1288–1295
Liu J-Y, Zheng Y, Li Y-G, Pan L, Li Y-S, Hu N-H (2005) Fe(II) and Co(II) pyridinebisimine complexes bearing different substituents on ortho- and para-position of imines: synthesis, characterization and behavior of ethylene polymerization. J Organomet Chem 690:1233–1239
Zhang Y, Sun W-H, Li T, Yang X (2004) Influence of electronic effect on catalytic activity of bis(imino)pyridyl Fe(II) and bis(imino)pyrimidyl Fe(II) complexes. J Mol Catal A Chem 218:119–124
Ivanchev SS, Tolstikov GA, Badaev VK, Oleinik II, Ivancheva NI, Rogozin DG, Oleinik IV, Myakin SV (2004) New bis(arylimino)pyridyl complexes as components of catalysts for ethylene polymerization. Kinet Catal 45:176–182
Kissin YV, Qian C, Xie G, Chen Y (2006) Multi-center nature of ethylene polymerization catalysts based on 2, 6-bis(imino)pyridyl complexes of iron and cobalt. J Polym Sci Part A Polym Chem 44:6159–6170
Saito J, Mitani M, Mohri J, Yoshida Y, Matsui S, Ishii S, Kojoh S, Kashiwa N, Fujita T (2001) Living polymerization of ethylene with a titanium complex containing two phenoxy-imine chelate ligands. Angew Chem Int Ed 40:2918–2920
Saito J, Mitani M, Onda M, Mohri J, Ishii S, Yoshida Y, Nakano T, Tanaka H, Matsugi T, Kojoh S, Kashiwa N, Fujita T (2001) Microstructure of highly syndiotactic living poly(propylene)s produced from a titanium complex with chelating fluorine-containing phenoxyimine ligands (an FI Catalyst). Macromol Rapid Commun 22:1072–1075
Qiu J, Li Y, Hu Y (2000) A new iron-based catalyst for ethylene polymerization. Polym Int 49:5–7
Ma Z, Wang H, Qiu J, Xu D, Hu Y (2001) A novel highly active iron/2, 6-bis(imino)pyridyl catalyst for ethylene polymerization. Macromol Rapid Commun 22:1280–1283
Ma Z, Sun W-H, Li Z-L, Shao C-X, Hu Y-L, Li X-H (2002) Ethylene polymerization by iron complexes with symmetrical and unsymmetrical ligands. Polym Int 51:994–997
Bianchini C, Giambastiani G, Guerrero IR, Meli A, Passaglia E, Gragnoli T (2004) Simultaneous polymerization and Schulz-Flory oligomerization of ethylene made possible by activation with MAO of a C 1-symmetric [2, 6-bis(arylimino)pyridyl]iron dichloride precursor. Organometallics 23:6087–6089
Kim I, Han BH, Ha Y-S, Ha C-S, Park D-W (2004) Effect of substituent position on the ethylene polymerization by Fe(II) and Co(II) pyridyl bis-imine catalysts. Catal Today 93–95:281–285
Görl C, Alt HG (2007) Iron complexes with ?-alkenyl substituted bis(arylimino)pyridine ligands as catalyst precursors for the oligomerization and polymerization of ethylene. J Mol Catal A Chem 273:118–132
Zhang Z, Chen S, Zhang X, Li H, Ke Y, Lu Y, Hu Y (2005) A series of novel 2, 6-bis(imino)pyridyl iron catalysts: synthesis, characterization and ethylene oligomerization. J Mol Catal A Chem 230:1–8
Bianchini C, Giambastiani G, Mantovani G, Meli A, Mimeau D (2004) Oligomerisation of ethylene to linear ?-olefins by tetrahedral cobalt(II) precursors stabilised by benzo[b]thiophen-2-yl-substituted (imino)pyridine ligands. J Organomet Chem 689:1356–1361
Bianchini C, Gatteschi D, Giambastiani G, Rios IG, Ienco A, Laschi F, Mealli C, Meli A, Sorace L, Toti A, Vizza F (2007) Electronic influence of the thienyl sulfur atom on the oligomerization of ethylene by cobalt(II) 6-(thienyl)-2-(imino)pyridine catalysis. Organometallics 26:726–739
Bianchini C, Mantovani G, Meli A, Migliacci F, Laschi F (2003) Selective oligomerization of ethylene to linear ?-olefins by tetrahedral cobalt(II) complexes with 6-(organyl)-2-(imino)pyridyl ligands: influence of the heteroatom in the organyl group on the catalytic activity. Organometallics 22:2545–2547
Champouret YDM, Maréchal J, Chaggar RK, Fawcett J, Singh K, Maseras F, Solan GA (2007) Factors affecting imine coordination in (iminoterpyridine)MX2 (M = Fe, Co, Ni, Zn): synthesis, structures, DFT calculations and ethylene oligomerisation studies. New J Chem 31:75–85
Sun W-H, Tang X, Gao T, Wu B, Zhang W, Ma H (2004) Synthesis, characterization, and ethylene oligomerization and polymerization of ferrous and cobaltous 2-(ethylcarboxylato)-6-iminopyridyl complexes. Organometallics 23:5037–5047
Fernandes S, Bellabarba RM, Ribeiro AFG, Gomes PT, Ascenso J, Mano JF, Dias AR, Marques MM (2002) Polymerisation of ethylene catalysed by mono-imine-2, 6-diacetylpyridine iron/methylaluminoxane (MAO) catalyst system: effect of the ligand on polymer microstructure. Polym Int 51:1301–1303
Sun W-H, Hao P, Li G, Zhang S, Wang W, Yi J, Asma M, Tang N (2007) Synthesis and characterization of iron and cobalt dichloride bearing 2-quinoxalinyl-6-iminopyridines and their catalytic behavior toward ethylene reactivity. J Organomet Chem 692:4506–4518
Su B-Y, Zhao J-S (2006) Preparation, structure and ethylene polymerization/oligomerization behavior of 2-carbethoxy-6-iminopyridine-based transition metal complexes. Polyhedron 25:3289–3298
Su B-Y, Zhao J-S, Gao Q-C (2007) Crystal structure and ethylene oligomerization catalytic activity of {2-carbethoxy-6-[1-[(2, 6-diethylphenyl) imino]ethyl]pyridine}CoCl2. Chin J Chem 25:121–124
Gibson VC, Redshaw C, Solan GA, White AJP, Williams DJ (2007) Aluminum alkyl-mediated route to novel N, N, O-chelates for five-coordinate iron(II) chloride complexes: synthesis, structures, and ethylene polymerization studies. Organometallics 26:5119–5123
Wang K, Wedeking K, Zuo W, Zhang D, Sun W-H (2008) Iron(II) and cobalt(II) complexes bearing N-((pyridin-2-yl)methylene)-quinolin-8-amine derivatives: synthesis and application to ethylene oligomerization. J Organomet Chem 693:1073–1080
Lappalainen K, Yliheikkilä K, Abu-Surrah AS, Polamo M, Leskelä M, Repo T (2005) Iron(II)- and cobalt(II) complexes with tridentate bis(imino)pyridine nitrogen ligands bearing chiral bulky aliphatic and aromatic substituents: crystal structure of [CoCl2{2, 6-bis[R-(+)-(bornylimino)methyl]pyridine}]. Z Anorg Allg Chem 631:763–768
Davis RN, Tanski JM, Adrian JC Jr, Tyler LA (2007) Variations in the coordination environment of Co2+, Cu2+ and Zn2+ complexes prepared from a tridentate (imino)pyridine ligand and their structural comparisons. Inorg Chim Acta 360:3061–3068
Bianchini C, Mantovani G, Meli A, Migliacci F, Zanobini F, Laschi F, Sommazzi A (2003) Oligomerisation of ethylene to linear ?-olefins by new C s- and C 1-symmetric [2,6-bis(imino)pyridyl]iron and -cobalt dichloride complexes. Eur J Inorg Chem 1620–1631
Wallenhorst C, Kehr G, Luftmann H, Fröhlich R, Erker G (2008) Bis(iminoethyl)pyridine systems with a pendant alkenyl group. Part A: cobalt and iron complexes and their catalytic behavior. Organometallics 27:6547–6556
Pelascini F, Wesolek M, Peruch F, Lutz PJ (2006) Modified pyridine-bis(imine) iron and cobalt complexes: synthesis, structure, and ethylene polymerization study. Eur J Inorg Chem 4309–4316
Cámpora J, Pérez CM, Rodríguez-Delgado A, Naz AM, Palma P, Alvarez E (2007) Selective alkylation of 2, 6-diiminopyridine ligands by dialkylmanganese reagents: a “one-pot” synthetic methodology. Organometallics 26:1104–1107
Cámpora J, Naz AM, Palma P, Rodríguez-Delgado A, Álvarez E, Tritto I, Boggioni L (2008) Iron and cobalt complexes of 4-alkyl-2,6-diiminopyridine ligands: synthesis and ethylene polymerization catalysis. Eur J Inorg Chem 1871–1879
Nückel S, Burger P (2001) Transition metal complexes with sterically demanding ligands, 3. Synthetic access to square-planar terdentate pyridine-diimine rhodium(I) and iridium(I) methyl complexes: successful detour via reactive triflate and methoxide complexes. Organometallics 20:4345–4359
Ionkin AS, Johnson LK (2008) Catalysts for olefin polymerization or oligomerization. US7442819
Beaufort L, Benvenuti F, Noels AF (2006) Iron(II)–ethylene polymerization catalysts bearing 2, 6-bis(imino)pyrazine ligands Part I. Synthesis and characterization. J Mol Catal A Chem 260:210–214
Beaufort L, Benvenuti F, Noels AF (2006) Iron(II)–ethylene polymerization catalysts bearing 2, 6-bis(imino)pyrazine ligands Part II. Catalytic behaviour, homogeneous and heterogeneous insights. J Mol Catal A Chem 260:215–220
Britovsek GJP, Gibson VC, Hoarau OD, Spitzmesser SK, White AJP, Williams DJ (2003) Iron and cobalt ethylene polymerization catalysts: variations on the central donor. Inorg Chem 42:3454–3465
Tenza K, Hanton MJ, Slawin AMZ (2009) Ethylene oligomerization using first-row transition metal complexes featuring heterocyclic variants of bis(imino)pyridine ligands. Organometallics 28:4852–4867
Dawson DM, Walker DA, Thornton-Pett M, Bochmann M (2000) Synthesis and reactivity of sterically hindered iminopyrrolato complexes of zirconium, iron, cobalt and nickel. Dalton Trans 459–466
Gibson VC, Spitzmesser SK, White AJP, Williams DJ (2003) Synthesis and reactivity of 1,8-bis(imino)carbazolide complexes of iron, cobalt and manganese. Dalton Trans 2718–2727
Wang L, Sun W-H, Han L, Li Z, Hu Y, He C, Yan C (2002) Cobalt and nickel complexes bearing 2, 6-bis (imino) phenoxy ligands: syntheses, structures and oligomerization studies. J Organomet Chem 650:59–64
Han L, Du J, Yang H, Wang H, Leng X, Galstyan A, Zari? S, Sun W (2003) Crystal structure and modeling calculation of the columnar helix 2, 6-bis(imino)phenoxy iron(III) chloride. Inorg Chem Comm 6:5–9
Zhang S, Sun W-H, Xiao T, Hao X (2010) Ferrous and cobaltous chlorides bearing 2, 8-bis(imino)quinolines: highly active catalysts for ethylene polymerization at high temperature. Organometallics 29:1168–1173
Britovsek GJP, Baugh SPD, Hoarau O, Gibson VC, Wass DF, White AJP, Williams DJ (2003) The role of bulky substituents in the polymerization of ethylene using late transition metal catalysts: a comparative study of nickel and iron catalyst systems. Inorg Chim Acta 345:279–291
Wang L, Sun W-H, Han L, Yang H, Hu Y, Jin X (2002) Late transition metal complexes bearing 2, 9-bis(imino)-1, 10-phenanthrolinyl ligands: synthesis, characterization and their ethylene activity. J Organomet Chem 658:62–70
Overett MJ, Meijboom R, Moss JR (2005) New iron bis(imino)pyridyl complexes containing dendritic wedges for alkene oligomerisation. Dalton Trans 551–555
Amort C, Malaun M, Krajete A, Kopacka H, Wurst K, Christ M, Lilge D, Kristen MO, Bildstein B (2002) N-pyrrolyl-[N, N, N]-bis(imino)pyridyl iron(II) and cobalt(II) olefin polymerization catalysts. Appl Organomet Chem 16:506–516
Britovsek GJP, Gibson VC, Mastroianni S, Oakes DCH, Redshaw C, Solan GA, White AJP, Williams DJ (2001) Imine versus amine donors in iron-based ethylene polymerisation catalysts. Eur J Inorg Chem 431–437
Bruce M, Gibson VC, Redshaw C, Solan GA, White AJP, Williams DJ (1998) Cationic alkyl aluminium ethylene polymerization catalysts based on monoanionic N,N,N-pyridyliminoamide ligands. Chem Commun 2523–2524
Guérin F, McConville DH, Vittal JJ (1996) Conformationally rigid diamide complexes of zirconium: electron deficient analogues of Cp2Zr. Organometallics 15:5586–5590
Britovsek GJP, England J, Spitzmesser SK, White AJP, Williams DJ (2005) Synthesis of iron(II), manganese(II), cobalt(II) and ruthenium(II) complexes containing tridentate nitrogen ligands and their application in the catalytic oxidation of alkanes. Dalton Trans 945–955
Vedder C, Schaper F, Brintzinger H, Kettunen M, Babik S, Fink G (2005) Chiral iron(II) and cobalt(II) complexes with biphenyl-bridged bis(pyridylimine) ligands—syntheses, structures and reactivities. Eur J Inorg Chem 1071–1080
Gao R, Wang K, Li Y, Wang F, Sun W-H, Redshaw C, Bochmann M (2009) 2-Benzoxazolyl-6-(1-(arylimino)ethyl)pyridyl cobalt (II) chlorides: a temperature switch catalyst in oligomerization and polymerization of ethylene. J Mol Catal A Chem 309:166–171
Gao R, Li Y, Wang F, Sun W-H, Bochmann M (2009) 2-Benzoxazolyl-6-[1-(arylimino)ethyl]pyridyliron(II) chlorides as ethylene oligomerization catalysts. Eur J Inorg Chem 4149–4156
Gao R, Zhang M, Liang T, Wang F, Sun W (2008) Nickel(II) complexes chelated by 2-arylimino-6-benzoxazolylpyridine: syntheses, characterization, and ethylene oligomerization. Organometallics 27:5641–5648
Hao P, Chen Y, Xiao T, Sun W-H (2010) Iron(III) complexes bearing 2-(benzimidazole)-6-(1-aryliminoethyl)pyridines: synthesis, characterization and their catalytic behaviors toward ethylene oligomerization and polymerization. J Organomet Chem 695:90–95
Chen Y, Hao P, Zuo W, Gao K, Sun W-H (2008) 2-(1-Isopropyl-2-benzimidazolyl)-6-(1-aryliminoethyl)pyridyl transition metal (Fe, Co, and Ni) dichlorides: syntheses, characterizations and their catalytic behaviors toward ethylene reactivity. J Organomet Chem 693:1829–1840
Xiao L, Gao R, Zhang M, Li Y, Cao X, Sun W-H (2009) 2-(1H–2-benzimidazolyl)-6-(1-(arylimino)ethyl)pyridyl iron(II) and cobalt(II) dichlorides: syntheses, characterizations, and catalytic behaviors toward ethylene reactivity. Organometallics 28:2225–2233
Sun W-H, Hao P, Zhang S, Shi Q, Zuo W, Tang X, Lu X (2007) Iron(II) and cobalt(II) 2-(benzimidazolyl)-6-(1-(arylimino)ethyl)pyridyl complexes as catalysts for ethylene oligomerization and polymerization. Organometallics 26:2720–2734
Wang K, Hao P, Zhang D, Sun W-H (2008) Tridentate NˆNˆN iron(II) and cobalt(II) complexes of ion-paired structures: synthesis, characterization and magnetism. J Mol Struct 890:95–100
Karam AR, Catarí EL, López-Linares F, Agrifoglio G, Albano CL, Díaz-Barrios A, Lehmann TE, Pekerar SV, Albornoz LA, Atencio R, González T, Ortega HB, Joskowics P (2005) Synthesis, characterization and olefin polymerization studies of iron(II) and cobalt(II) catalysts bearing 2, 6-bis(pyrazol-1-yl)pyridines and 2, 6-bis(pyrazol-1-ylmethyl)pyridines ligands. Appl Catal A Gen 280:165–173
Calderazzo F, Englert U, Hub C, Marchetti F, Pampaloni G, Passarelli V, Romano A, Santi R (2003) Synthesis and structural characterization of iron(II) derivatives of heterocyclic tridentate amines. Inorg Chim Acta 344:197–206
Zabel D, Schubert A, Wolmershäuser G, Jones Jr RL, Thiel WR (2008) Iron and cobalt complexes of tridentate N-donor ligands in ethylene polymerization: efficient shielding of the active sites by simple phenyl groups. Eur J Inorg Chem 3648–3654
Imanishi Y, Nomura K (2000) Olefin polymerization and copolymerization with soluble transition-metal complex catalysts. J Polym Sci Part A Polym Chem 38:4613–4626
Tondreau AM, Darmon LM, Wile BM, Floyd SK, Lobkovsky E, Chirik PJ (2009) Enantiopure pyridine bis(oxazoline) “Pybox” and bis(oxazoline) “Box” iron dialkyl complexes: comparison to bis(imino)pyridine compounds and application to catalytic hydrosilylation of ketones. Organometallics 28:3928–3940
Nakayama Y, Baba Y, Yasuda H, Kawakita K, Ueyama N (2003) Stereospecific polymerizations of conjugated dienes by single site iron complexes having chelating N, N, N-donor ligands. Macromolecules 36:7953–7958
Danopoulos AA, Tsoureas N, Wright JA, Light ME (2004) N-Heterocyclic pincer dicarbene complexes of iron(II): C-2 and C-5 metalated carbenes on the same metal center. Organometallics 23:166–168
McGuinness DS, Gibson VC, Steed JW (2004) Bis(carbene)pyridine complexes of the early to middle transition metals: survey of ethylene oligomerization and polymerization capability. Organometallics 23:6288–6292
Danopoulos AA, Wright JA, Motherwell WB, Ellwood S (2004) N-Heterocyclic “Pincer” dicarbene complexes of cobalt(I), cobalt(II), and cobalt(III). Organometallics 23:4807–4810
Al-Benna S, Sarsfield MJ, Thornton-Pett M, Ormsby DL, Maddox PJ, Brès P, Bochmann M (2000) Sterically hindered iminophosphorane complexes of vanadium, iron, cobalt and nickel: a synthetic, structural and catalytic study. Dalton Trans 4247–4257
Müllera G, Klinga M, Leskelä M, Rieger B (2002) Iron and cobalt complexes of a series of tridentate P, N, P ligands synthesis, characterization, and application in ethene polymerization reactions. Z Anorg Allg Chem 628:2839–2846
Sun W-H, Jie S, Zhang S, Zhang W, Song Y, Ma H, Chen J, Wedeking K, Fröhlich R (2006) Iron complexes bearing 2-imino-1, 10-phenanthrolinyl ligands as highly active catalysts for ethylene oligomerization. Organometallics 25:666–677
Jie S, Zhang S, Wedeking K, Zhang W, Ma H, Lu X, Deng Y, Sun W-H (2006) Cobalt(II) complexes bearing 2-imino-1, 10-phenanthroline ligands: synthesis, characterization and ethylene oligomerization. C R Chim 9:1500–1509
Jie S, Zhang S, Sun W-H, Kuang X, Liu T, Guo J (2007) Iron(II) complexes ligated by 2-imino-1, 10-phenanthrolines: preparation and catalytic behavior toward ethylene oligomerization. J Mol Catal A Chem 269:85–96
Zhang M, Zhang W, Xiao T, Xiang J-F, Hao X, Sun W-H (2010) 2-Ethyl-ketimino-1, 10-phenanthroline iron(II) complexes as highly active catalysts for ethylene oligomerization. J Mol Catal A Chem 320:92–96
Jie S, Zhang S, Sun W-H (2007) 2-Arylimino-9-phenyl-1,10-phenanthrolinyl-iron, -cobalt and -nickel complexes: synthesis, characterization and ethylene oligomerization behavior. Eur J Inorg Chem 5584–5598
Pelletier JDA, Champouret YDM, Cadarso J, Clowes L, Gañete M, Singh K, Thanarajasingham V, Solan GA (2006) Electronically variable imino-phenanthrolinyl-cobalt complexes; synthesis, structures and ethylene oligomerisation studies. J Organomet Chem 691:4114–4123
Zhang M, Hao P, Zuo W, Jie S, Sun W-H (2008) 2-(Benzimidazol-2-yl)-1, 10-phenanthrolyl metal (Fe and Co) complexes and their catalytic behaviors toward ethylene oligomerization. J Organomet Chem 693:483–491
Zhang M, Gao R, Hao X, Sun W-H (2008) 2-Oxazoline/benzoxazole-1, 10-phenanthrolinylmetal (iron, cobalt or nickel) dichloride: synthesis, characterization and their catalytic reactivity for the ethylene oligomerization. J Organomet Chem 693:3867–3877
Wang L, Ren H, Sun J (2008) Fe(acac)3-bis(imino)pyridine/MAO: a new catalytic system for ethylene polymerization. J Appl Polym Sci 108:167–173
Wang L, Sun J (2008) Methylene bridged binuclear bis(imino)pyridyl iron(II) complexes and their use as catalysts together with Al(i-Bu)3 for ethylene polymerization. Inorg Chim Acta 361:1843–1849
Liu J, Li Y, Liu J, Li Z (2005) Ethylene polymerization with a highly active and long-lifetime macrocycle trinuclear 2, 6-bis(imino)pyridyliron. Macromolecules 38:2559–2563
Tolstikov GA, Ivanchev SS, Oleinik II, Ivancheva NI, Oleinik IV (2005) New multifunctional bis(imino)pyridine-iron chloride complexes and ethylene polymerization catalysts on their basis. Doklady Phys Chem 404:182–185
Zheng Z-J, Chen J, Li Y-S (2004) The synthesis and catalytic activity of poly(bis(imino)pyridyl) iron(II) metallodendrimer. J Organomet Chem 689:3040–3045
Khamker Q, Champouret YDM, Singh K, Solan GA (2009) Bis(imino)quaterpyridine-bearing multimetallic late transition metal complexes as ethylene oligomerisation catalysts. Dalton Trans 8935–8944
Barbaro P, Bianchini C, Giambastiani G, Rios IG, Meli A, Oberhauser W, Segarra AM, Sorace L, Toti A (2007) Synthesis of new polydentate nitrogen ligands and their use in ethylene polymerization in conjunction with iron(II) and cobalt(II) bis-halides and methylaluminoxane. Organometallics 26:4639–4651
Bianchini C, Giambastiani G, Rios IG, Meli A, Oberhauser W, Sorace L, Toti A (2007) Synthesis of a new polydentate ligand obtained by coupling 2, 6-bis(imino)pyridine and (imino)pyridine moieties and its use in ethylene oligomerization in conjunction with iron(II) and cobalt(II) bis-halides. Organometallics 26:5066–5078
Zhang S, Vystorop I, Tang Z, Sun W-H (2007) Bimetallic (iron or cobalt) complexes bearing 2-methyl-2, 4-bis(6-iminopyridin-2-yl)-1H–1, 5-benzodiazepines for ethylene reactivity. Organometallics 26:2456–2460
Talsi EP, Babushkin DE, Semikolenova NV, Zudin VN, Panchenko VN, Zakharov VA (2001) Polymerization of ethylene catalyzed by iron complex bearing 2, 6-bis(imine)pyridyl ligand: 1H and 2H NMR monitoring of ferrous species formed via catalyst activation with AlMe3, MAO, AlMe3/B(C6F5)3 and AlMe3/CPh3B(C6F5)4. Macromol Chem Phys 202:2046–2051
Castro PM, Lahtinen P, Axenov K, Viidanoja J, Kotiaho T, Leskelä M, Repo T (2005) Activation of 2, 6-bis(imino)pyridine iron(II) chloride complexes by methylaluminoxane: an electrospray ionization tandem mass spectrometry investigation. Organometallics 24:3664–3670
Bryliakov KP, Talsi EP, Semikolenova NV, Zakharov VA (2009) Formation and nature of the active sites in bis(imino)pyridine iron-based polymerization catalysts. Organometallics 28:3225–3232
Deng L, Margl P, Ziegler T (1999) Mechanistic aspects of ethylene polymerization by iron(II)-bisimine pyridine catalysts: a combined density functional theory and molecular mechanics study. J Am Chem Soc 121:6479–6487
Griffiths EAH, Britovsek GJP, Gibson VC, Gould IR (1999) Highly active ethylene polymerisation catalysts based on iron: an ab initio study. Chem Commun 1333–1334
Khoroshun DV, Musaev DG, Vreven T, Morokuma K (2001) Theoretical study on bis(imino)pyridyl-Fe(II) olefin poly- and oligomerization catalysts. Dominance of different spin states in propagation and ?-hydride transfer pathways. Organometallics 20:2007–2026
Bryliakov KP, Semikolenova NV, Zakharov VA, Talsi EP (2004) Active intermediates of ethylene polymerization over 2, 6-bis(imino)pyridyl iron complex activated with aluminum trialkyls and methylaluminoxane. Organometallics 23:5375–5378
Bouwkamp MW, Bart SC, Hawrelak EJ, Trovitch RJ, Lobkovsky E, Chirik PJ (2005) Square planar bis(imino)pyridine iron halide and alkyl complexe. Chem Commun 3406–3408
Fernández I, Trovitch RJ, Lobkovsky E, Chirik PJ (2008) Synthesis of bis(imino)pyridine iron di- and monoalkyl complexes: stability differences between FeCH2SiMe3 and FeCH2CMe3 derivatives. Organometallics 27:109–118
Scott J, Gambarotta S, Korobkov I, Budzelaar PHM (2005) Reduction of (diiminopyridine)iron: evidence for a noncationic polymerization pathway? Organometallics 24:6298–6300
Cámpora J, Naz AM, Palma P, Álvarez E, Reyes ML (2005) 2, 6-Diiminopyridine iron(II) dialkyl complexes. Interaction with aluminum alkyls and ethylene polymerization catalysis. Organometallics 24:4878–4881
Scott J, Gambarotta S, Korobkov I, Budzelaar PHM (2005) Metal versus ligand alkylation in the reactivity of the (bis-iminopyridinato)Fe catalyst. J Am Chem Soc 127:13019–13029
Bouwkamp MW, Lobkovsky E, Chirik PJ (2005) Bis(imino)pyridine iron(II) alkyl cations for olefin polymerization. J Am Chem Soc 127:9660–9661
Trovitch RJ, Lobkovsky E, Chirik PJ (2008) Bis(imino)pyridine iron alkyls containing ?-hydrogens: synthesis, evaluation of kinetic stability, and decomposition pathways involving chelate participation. J Am Chem Soc 130:11631–11640
Bart SC, Ch?opek K, Bill E, Bouwkamp MW, Lobkovsky E, Neese F, Wieghardt K, Chirik PJ (2006) Electronic structure of bis(imino)pyridine iron dichloride, monochloride, and neutral ligand complexes: a combined structural, spectroscopic, and computational study. J Am Chem Soc 128:13901–13912
Bart SC, Lobkovsky E, Chirik PJ (2004) Preparation and molecular and electronic structures of iron(0) dinitrogen and silane complexes and their application to catalytic hydrogenation and hydrosilation. J Am Chem Soc 126:13794–13807
Margl P, Deng L, Ziegler T (1999) Cobalt(II) imino pyridine assisted ethylene polymerization: a quantum-mechanical/molecular-mechanical density functional theory investigation. Organometallics 18:5701–5708
Gibson VC, Humphries MJ, Tellmann KP, Wass DF, White AJP, Williams DJ (2001) The nature of the active species in bis(imino)pyridyl cobalt ethylene polymerisation catalysts. Chem Commun 2252–2253
Kooistra TM, Knijnenburg Q, Smits JMM, Horton AD, Budzelaar PHM, Gal AW (2001) Olefin polymerization with [{bis(imino)pyridyl}CoIICl2]: generation of the active species involves CoI. Angew Chem Int Ed 40:4719–4722
Steffen W, Blömker T, Kleigrewe N, Kehr G, Fröhlich R, Erker G (2004) Generation of bis(iminoalkyl)pyridine cobalt(I) cations under metal alkyl free conditions that polymerize ethane. Chem Commun 1188–1189
Gibson VC, Tellmann KP, Humphries MJ, Wass DF (2002) Bis(imino)pyridine cobalt alkyl complexes and their reactivity toward ethylene: a model system for ?-hydrogen chain transfer. Chem Commun 2316–2317
Tellmann KP, Humphries MJ, Rzepa HS, Gibson VC (2004) Experimental and computational study of ?-H transfer between cobalt(I) alkyl complexes and 1-alkenes. Organometallics 23:5503–5513
Semikolenova NV, Zakharov VA, Talsi EP, Babushkin DE, Sobolev AP, Echevskaya LG, Khysniyarov MM (2002) Study of the ethylene polymerization over homogeneous and supported catalysts based on 2, 6-bis(imino)pyridyl complexes of Fe(II) and Co(II). J Mol Catal A Chem 182–183:283–294
Soshnikov IE, Semikolenova NV, Bushmelev AN, Bryliakov KP, Lyakin OY, Redshaw C, Zakharov VA, Talsi EP (2009) Investigating the nature of the active species in bis(imino)pyridine cobalt ethylene polymerization catalysts. Organometallics 28:6003–6013
Humphries MJ, Tellmann KP, Gibson VC, White AJP, Williams DJ (2005) Investigations into the mechanism of activation and initiation of ethylene polymerization by bis(imino)pyridine cobalt catalysts: synthesis, structures, and deuterium labeling studies. Organometallics 24:2039–2050
Knijnenburg Q, Hetterscheid D, Kooistra TM, Budzelaar PHM (2004) The electronic structure of (diiminopyridine)cobalt(I) complexes. Eur J Inorg Chem 1204–1211
Bowman AC, Milsmann C, Atienza CCH, Lobkovsky E, Wieghardt K, Chirik PJ (2010) Synthesis and molecular and electronic structures of reduced bis(imino)pyridine cobalt dinitrogen complexes: ligand versus metal reduction. J Am Chem Soc 132:1676–1684
Tomov AK, Gibson VC, Britovsek GJP, Long RJ, Meurs M, Jones DJ, Tellmann KP, Chirinos JJ (2009) Distinguishing chain growth mechanisms in metal-catalyzed olefin oligomerization and polymerization systems: C2H4/C2D4 co-oligomerization/polymerization experiments using chromium, iron, and cobalt catalysts. Organometallics 28:7033–7040
Barabanov AA, Bukatov GD, Zakharov VA, Semikolenova NV, Echevskaja LG, Matsko MA (2005) Kinetic peculiarities of ethylene polymerization over homogeneous bis(imino)pyridine Fe(II) catalysts with different activators. Macromol Chem Phys 206:2292–2298
Wang S, Liu D, Mao B (2009) Characterization of compositional heterogeneity in the polyethylene prepared with bis(imino)pyridyl iron(II) precatalyst and triethylaluminum. J Appl Polym Sci 111:1151–1155
Wang S, Liu D, Huang R, Zhang Y, Mao B (2006) Studies on the activation and polymerization mechanism of ethylene polymerization catalyzed by bis(imino)pyridyl iron(II) precatalyst with alkylaluminum. J Mol Catal A Chem 245:122–131
Britovsek GJP, Cohen SA, Gibson VC, Maddox PJ, Meurs M (2002) Iron-catalyzed polyethylene chain growth on zinc: linear ?-olefins with a Poisson distribution. Angew Chem Int Ed 41:489–491
Britovsek GJP, Cohen SA, Gibson VC, Meurs M (2004) Iron catalyzed polyethylene chain growth on zinc: a study of the factors delineating chain transfer versus catalyzed chain growth in zinc and related metal alkyl systems. J Am Chem Soc 126:10701–10712
Wang Q, Li L, Fan Z (2005) Effects of tetraalkylaluminoxane activators on ethylene polymerization catalyzed by iron-based complexes. Eur Polym J 41:1170–1176
Li L, Wang Q, Fan ZQ (2004) Synthesis of polyethylene with bimodal molecular weight distribution by iron-based late transition metal catalyst/various aluminoxanes system. Chem J Chin Univ 25:1777–1779
Wang Q, Li L (2004) Effect of aluminoxane on molecular weight and molecular weight distribution of polyethylene prepared by an iron-based catalyst. Polym Int 53:1473–1478
Wang Q, Li L, Fan Z (2004) Polyethylene with bimodal molecular weight distribution synthesized by 2, 6-bis(imino)pyridyl complexes of Fe(II) activated with various activators. Eur Polym J 40:1881–1886
Wang Q, Li L, Fan Z (2005) Effect of alkylaluminum on ethylene polymerization catalyzed by 2, 6-bis(imino)pyridyl complexes of Fe(II). J Polym Sci Part A Polym Chem 43:1599–1606
Li L, Wang Q (2004) Synthesis of polyethylene with bimodal molecular weight distribution by supported iron-based catalyst. J Polym Sci Part A Polym Chem 42:5662–5669
Radhakrishnan K, Cramail H, Deffieux A, François P, Momtaz A (2003) Influence of alkylaluminium activators and mixtures thereof on ethylene polymerization with a tridentate bis(imino)pyridinyliron complex. Macromol Rapid Commun 24:251–254
Kumar KR, Sivaram S (2000) Ethylene polymerization using iron(II)bis(imino) pyridyl and nickel (diimine) catalysts: effect of cocatalysts and reaction parameters. Macromol Chem Phys 201:1513–1520
Wang Q, Yang H, Fan Z (2002) Efficient activators for an iron catalyst in the polymerization of ethylene. Macromol Rapid Commun 23:639–642
Knijnenburg Q, Smits JMM, Budzelaar PHM (2006) Reaction of the diimine pyridine ligand with aluminum alkyls: an unexpectedly complex reaction. Organometallics 25:1036–1046
Knijnenburg Q, Smits JMM, Budzelaar PHM (2004) Reaction of AlEt2Cl with the diiminepyridine ligand: an unexpected product. C R Chim 7:865–869
Scott J, Gambarotta S, Korobkov I, Knijnenburg Q, Bruin B, Budzelaar PHM (2005) Formation of a paramagnetic Al complex and extrusion of Fe during the reaction of (diiminepyridine)Fe with AlR3 (R = Me, Et). J Am Chem Soc 127:17204–17206
Yang H, Wang Q, Fan Z, Xu H (2004) Improved high-temperature performance of iron (II) complexes for ethylene polymerization by variation of aluminoxanes. Polym Int 53:37–40
Wang Q, Yang H, Fan Z, Xu H (2004) Performance of various activators in ethylene polymerization based on an iron(II) catalyst system. J Polym Sci Part A Polym Chem 42:1093–1099
Tudella J, Ribeiro MR, Cramail H, Deffieux A (2007) Novel organic activators for single site iron catalysts. Macromol Chem Phys 208:815–822
Ramos J, Cruz V, Muñoz-Escalona A, Martínez-Salazar J (2002) A computational study of iron-based Gibson-Brookhart catalysts for the copolymerization of ethylene and 1-hexene. Polymer 43:3635–3645
Takeuchi D, Matsuura R, Park S, Osakada K (2007) Cyclopolymerization of 1, 6-heptadienes catalyzed by iron and cobalt complexes: synthesis of polymers with trans- or cis-fused 1, 2-cyclopentanediyl groups depending on the catalyst. J Am Chem Soc 129:7002–7003
Takeuchi D, Matsuura R, Fukuda Y, Osakada K (2009) Selective cyclopolymerization of ?,?-dienes and copolymerization with ethylene catalyzed by Fe and Co complexes. Dalton Trans 8955–8962
Takeuchi D, Osakada K (2008) New polymerization of dienes and related monomers catalyzed by late transition metal complexes. Polymer 49:4911–4924
Takeuchi D, Matsuura R, Osakada K (2008) Copolymerization of hepta-1, 6-diene with ethylene catalyzed by cobalt complexes. Macromol Rapid Commun 29:1932–1936
Takeuchi D, Anada K, Osakada K (2004) Cobalt-complex-catalyzed copolymerization of ethylene with 2-aryl-1-methylenecyclopropanes. Angew Chem Int Ed 43:1233–1235
Takeuchi D, Osakada K (2005) Alternating copolymerization of ethylene with 7-methylenebicyclo[4.1.0]heptane promoted by the cobalt complex. Highly regulated structure and thermal rearrangement of the obtained copolymer. Macromolecules 38:1528–1530
Pelascini F, Peruch F, Lutz PJ, Wesolek M, Kress J (2003) Polymerization of norbornene with CoCl2 and pyridine bisimine cobalt(II) complexes activated with MAO. Macromol Rapid Commun 24:768–771
Pelascini F, Peruch F, Lutz PJ, Wesolek M, Kress J (2004) Polymerization of norbornene with Co(II) complexes. Macromol Symp 213:265–274
Sacchi MC, Sonzogni M, Losio S, Forlini F, Locatelli P, Tritto I, Licchelli M (2001) Vinylic polymerization of norbornene by late transition metal-based catalysis. Macromol Chem Phys 202:2052–2058
Yliheikkilä K, Lappalainen K, Castro PM, Ibrahim K, Abu-Surrah A, Leskelä M, Repo T (2006) Polymerization of acrylate monomers with MAO activated iron(II) and cobalt(II) complexes bearing tri- and tetradentate nitrogen ligands. Eur Polym J 42:92–100
Castro PM, Lankinen MP, Uusitalo A, Leskelä M, Repo T (2004) Polymerization of acrylate monomers by iron(II) complexes bearing bis(imino)pyridyl or phosphine ligands. Macromol Symp 213:199–208
Abu-Surrah AS, Qaroush AK (2007) Polymerization of vinyl monomers via MAO activated iron(II) dichloro complexes bearing bis(imino)pyridine-, quinolinaldimine- and thiophenaldimine-based tridentate nitrogen ligands. Eur Polym J 43:2967–2974
Fullana MJ, Miri MJ, Vadhavkar SS, Kolhatkar N, Delis AC (2008) Polymerization of methyl acrylate and as comonomer with ethylene using a bis(imino)pyridine iron(II) chloride/methylaluminoxane catalyst. J Polym Sci Part A Polym Chem 46:5542–5558
Liu J, Zheng Y, Li Y (2004) Polymerization of methyl methacrylate by iron(II) pyridinebisimine complexes. Polymer 45:2297–2301
Kim I, Ha YS, Ha C-S (2004) Polymerization of vinyl ethers by iron(II) and cobalt(II) pyridyl bis(imine) complexes in the presence of methylaluminoxane. Macromol Rapid Commun 25:1069–1072
de Souza RF, Casagrande OL Jr (2001) Recent advances in olefin polymerization using binary catalyst systems. Macromol Rapid Commun 22:1293–1301
Komon ZJA, Bazan GC (2001) Synthesis of branched polyethylene by tandem catalysis. Macromol Rapid Commun 22:467–478
Mecking S (1999) Reactor blending with early/late transition metal catalyst combinations in ethylene polymerization. Macromol Rapid Commun 20:139–143
Long Y-Y, Liu S-R, Cui L, Li Y-S (2010) Influence of branching on the thermal and crystallization behavior of bimodal polyethylenes synthesized with binary late-transition-metal catalyst combinations. J Appl Polym Sci 115:3045–3055
Pan L, Zhang KY, Li YG, Bo SQ, Li YS (2007) Thermal and crystallization behaviors of polyethylene blends synthesized by binary late transition metal catalysts combinations. J Appl Polym Sci 104:4188–4198
Quijada R, Rojas R, Bazan G, Komon ZJA, Mauler RS, Galland GB (2001) Synthesis of branched polyethylene from ethylene by tandem action of iron and zirconium single site catalysts. Macromolecules 34:2411–2417
Bianchini C, Frediani M, Giambastiani G, Kaminsky W, Meli A, Passaglia E (2005) Amorphous polyethylene by tandem action of cobalt and titanium single-site catalysts. Macromol Rapid Commun 26:1218–1223
Frediani M, Piel C, Kaminsky W, Bianchini C, Rosi L (2006) Tandem copolymerization: an effective control of the level of branching and molecular weight distribution. Macromol Symp 236:124–133
Kukalyekar N, Balzano L, Peters GWM, Rastogi S, Chadwick JC (2009) Characteristics of bimodal polyethylene prepared via co-immobilization of chromium and iron catalysts on an MgCl2-based support. Macromol React Eng 3:448–454
Huang R, Koning C, Chadwick JC (2007) Synergetic effect of a nickel diimine in ethylene polymerization with immobilized Fe-, Cr-, and Ti-based catalysts on MgCl2 supports. Macromolecules 40:3021–3029
Ivanchev SS, Ivancheva NI, Khaikin SY, Sviridova EV, Rogozin DG (2006) Polymerization of ethylene by SiO2-supported two-component catalytic systems containing bis(imino)pyridine and bis(imine) ligands. Polym Sci Ser A 48:251–256
Wang H, Ma Z, Ke Y, Hu Y (2003) Synthesis of linear low density polyethylene (LLDPE) by in situ copolymerization with novel cobalt and zirconium catalysts. Polym Int 52:1546–1552
Ye Z, Zhu S (2003) Synthesis of branched polypropylene with isotactic backbone and atactic side chains by binary iron and zirconium single-site catalysts. J Polym Sci Part A Polym Chem 41:1152–1159
Zhang Z, Lua Z, Chen S, Li H, Zhang X, Lu Y, Hu Y (2005) Synthesis of branched polyethylene from ethylene stock by an interference-free tandem catalysis of TiCl4/MgCl2 and iron catalyst. J Mol Catal A Chem 236:87–93
Lu Z, Zhang Z, Li Y, Wu C, Hu Y (2006) Synthesis of branched polyethylene by in situ polymerization of ethylene with combined iron catalyst and Ziegler–Natta catalyst. J Appl Polym Sci 99:2898–2903
Xu H, Guo C-Y, Zhang M, Yang H-J, Dong J, Yuan G (2007) In situ copolymerization of ethylene to linear low-density polyethylene (LLDPE) with calcosilicate (CAS-1) supported dual-functional catalytic system. Catal Commun 8:2143–2149
Ma Z, Ke Y, Wang H, Guo C, Zhang M, Sun W-H, Hu Y (2003) Ethylene polymerization with a silica-supported iron-based diimine catalyst. J Appl Polym Sci 88:466–469
Helldörfer M, Alt HG, Ebenhoch J (2002) Microgels as new support materials for heterogeneous cocatalysts in ethylene polymerization reactions. J Appl Polym Sci 86:3021–3029
Seitz M, Milius W, Alt HG (2007) Iron(II) coordination compounds with ?-alkenyl substituted bis(imino)pyridine ligands: self-immobilizing catalysts for the polymerization of ethylene. J Mol Catal A Chem 261:246–253
Huanga R, Kukalyekar N, Koning CE, Chadwick JC (2006) Immobilization and activation of 2,6-bis(imino)pyridyl Fe, Cr and V precatalysts using a MgCl2/AlRn(OEt)3?n support: effects on polyethylene molecular weight and molecular weight distribution. J Mol Catal A Chem 260:135–143
Huanga R, Liu D, Wang S, Mao B (2005) Preparation of spherical MgCl2 supported bis(imino)pyridyl iron(II) precatalyst for ethylene polymerization. J Mol Catal A Chem 233:91–97
Paulino IS, Schuchardt U (2004) Ethylene polymerization using iron catalysts heterogenized in MCM-41. Catal Commun 5:5–7
Armspach D, Matt D, Peruch F, Lutz P (2003) Cyclodextrin-encapsulated iron catalysts for the polymerization of ethylene. Eur J Inorg Chem 805–809
Leone G, Bertini F, Canetti M, Boggioni L, Conzatti L, Tritto I (2009) Long-lived layered silicates-immobilized 2, 6-bis(imino)pyridyl iron(II) catalysts for hybrid polyethylene nanocomposites by in situ polymerization: effect of aryl ligand and silicate modification. J Polym Sci Part A Polym Chem 47:548–564
Huang R, Koning CE, Chadwick JC (2007) Effects of hydrogen in ethylene polymerization and oligomerization with magnesium chloride-supported bis(imino)pyridyl iron catalysts. J Polym Sci Part A Polym Chem 45:4054–4061
Kaul FAR, Puchta GT, Schneider H, Bielert F, Mihalios D, Herrmann WA (2002) Immobilization of bis(imino)pyridyliron(II) complexes on silica. Organometallics 21:74–82
Jin G, Zhang D (2004) Micron-granula polyolefin with self-immobilized nickel and iron diimine catalysts bearing one or two allyl groups. J Polym Sci Part A Polym Chem 42:1018–1024
Liu C, Jin G (2002) Polymer-incorporated iron catalysts for ethylene polymerization—a new approach to immobilize iron olefin catalysts on polystyrene chains. New J Chem 26:1485–1489
Zheng Z, Liu J, Li Y (2005) Ethylene polymerization with silica-supported bis(imino)pyridyl iron(II) catalysts. J Catal 234:101–110
Kim I, Han BH, Ha C-S, Kim J-K, Suh H (2003) Preparation of silica-supported bis(imino)pyridyl iron(II) and cobalt(II) catalysts for ethylene polymerization. Macromolecules 36:6689–6691
Ray S, Sivaram S (2006) Silica-supported bis(imino)pyridyl iron(II) catalyst: nature of the support–catalyst interactions. Polym Int 55:854–861
Barabanov AA, Bukatov GD, Zakharov VA (2008) Effect of temperature on the number of active sites and propagation rate constant at ethylene polymerization over supported bis(imino)pyridine iron catalysts. J Polym Sci Part A Polym Chem 46:6621–6629
Barabanov AA, Bukatov GD, Zakharov VA, Semikolenova NV, Mikenas TB, Echevskaja LG, Matsko MA (2006) Kinetic study of ethylene polymerization over supported bis(imino)pyridine iron(II) catalysts. Macromol Chem Phys 207:1368–1375
Ma Z, Sun W-H, Zhu N, Li Z, Shao C, Hu Y (2002) Preparation of silica-supported late transition metal catalyst and ethylene polymerization. Polym Int 51:349–352
Barabanov AA, Bukatov GD, Zakharov VA, Semikolenova NV, Echevskaja LG, Matsko MA (2008) Ethylene polymerization over homogeneous and supported catalysts based on bis(imino)pyridine Co(II) complex: data on the number of active centers and propagation rate constant. Macromol Chem Phys 209:2510–2515
Xu H, Guo C, Xue C, Ma Z, Zhang M, Dong J, Wang J, Hu Y (2006) Novel layered calcosilicate-immobilized iron-based diimine catalyst for ethylene polymerization. Eur Polym J 42:203–208
Schilling M, Bal R, Görl C, Alt HG (2007) Heterogeneous catalyst mixtures for the polymerization of ethylene. Polymer 48:7461–7475
Han W, Müller C, Vogt D, Niemantsverdriet H, Thüne PC (2006) Introducing a flat model of the silica-supported bis(imino)pyridyl iron(II) polyolefin catalyst. Macromol Rapid Commun 27:279–283
Han W, Niemantsverdriet H, Thüne PC (2007) A flat model approach to tethered bis(imino)pyridyl iron ethylene polymerization catalysts. Macromol Symp 260:147–153
Guo C-Y, Xu H, Zhang M, Zhang X, Yan F, Yuan G (2009) Immobilization of bis(imino)pyridine iron complexes onto mesoporous molecular sieves and their catalytic performance in ethylene oligomerization. Catal Commun 10:1467–1471
Zhang M, Xu H, Guo C, Ma Z, Dong J, Ke Y, Hu Y (2005) Ethylene polymerization with iron-based diimine catalyst supported on MCM-41. Polym Int 54:274–278
Guo C, Jin G-X, Wang F (2004) Preparation and characterization of SBA-15 supported iron(II)-bisimine pyridine catalyst for ethylene polymerization. J Polym Sci Part A Polym Chem 42:4830–4837
Huang R, Liu D, Wang S, Mao B (2004) Spherical MgCl2 supported iron catalyst for ethylene polymerization: effect of the preparation procedure on catalyst activity and the morphology of polyethylene particles. Macromol Chem Phys 205:966–972
Xu R, Liu D, Wang S, Mao B (2006) Preparation of spherical MgCl2-supported late-transition metal catalysts for ethylene polymerization. Macromol Chem Phys 207:779–786
Mikenas TB, Zakharov VA, Echevskaya LG, Matsko MA (2007) Kinetic features of ethylene polymerization over supported catalysts [2, 6-bis(imino)pyridyl iron dichloride/magnesium dichloride] with AlR3 as an activator. J Polym Sci Part A Polym Chem 45:5057–5066
Ray S, Galgali G, Lele A, Sivaram S (2005) In situ polymerization of ethylene with bis(imino)pyridine iron(II) catalysts supported on clay: the synthesis and characterization of polyethylene–clay nanocomposites. J Polym Sci Part A Polym Chem 43:304–318
Bouilhac C, Cloutet E, Deffieux A, Taton D, Cramail H (2007) Functional star-like polystyrenes as organic supports of MeDIP(2, 6-iPrPh)2FeCl2 catalyst toward ethylene polymerization. Macromol Chem Phys 208:1349–1361
Bouilhac C, Cloutet E, Cramail H, Deffieux A, Taton D (2005) Functionalized star-like polystyrenes as organic supports of a tridentate bis(imino)pyridinyliron/aluminic derivative catalytic system for ethylene polymerization. Macromol Rapid Commun 26:1619–1625
Laren MW, Duin MA, Klerk C, Naglia M, Rogolino D, Pelagatti P, Bacchi A, Pelizzi C, Elsevier CJ (2002) Palladium(0) complexes with unsymmetric bidentate nitrogen ligands for the stereoselective hydrogenation of 1-phenyl-1-propyne to (Z)-1-phenyl-1-propene. Organometallics 21:1546–1553
Arnáiz A, Cuevas JV, García-Herbosa G, Carbayo A, Casares JA, Gutierrez-Puebla E (2002) Revealing the diastereomeric nature of pincer terdentate nitrogen ligands 2,6-(arylaminomethyl)pyridine through coordination to palladium. Dalton Trans 2581–2586
Balamurugan R, Palaniandavar M, Halcrow MA (2006) Copper(II) complexes of sterically hindered Schiff base ligands: synthesis, structure, spectra and electrochemistry. Polyhedron 25:1077–1088
Holland JM, Liu X, Zhao JP, Mabbs FE, Kilner CA, Thornton-Pett M, Halcrow MA (2000) Copper complexes of 2,6-bis(iminomethyl)pyridine derivatives and of 1,3-bis(pyridine-2-yl)pyrazole. Effects of ligand bulk and conformational strain on the ground state of a six-co-ordinate copper(II) ion. Dalton Trans 3316–3324
Granifo J, Bird SJ, Orrell KG, Osborne AG, Šik V (1999) Synthesis and dynamic NMR studies of stereochemical non-rigidity in rhenium(I) complexes of 2, 6-bis[1-(phenylimino)ethyl]pyridine derivatives. Inorg Chim Acta 295:56–63
Çetinkaya B, Çetinkaya E, Brookhart M, White PS (1999) Ruthenium II complexes with 2, 6-pyridyl-diimine ligands: synthesis, characterization and catalytic activity in epoxidation reactions. J Mol Catal A Chem 142:101–112
Schmidt R, Hammon U, Gottfried S, Welch MB, Alt HG (2003) Iron(II)-based catalysts for ethene oligomerization. J Appl Polym Sci 88:476–482
Oleinik II, Oleinik IV, Abdrakhmanov IB, Ivanchev SS, Tolstikov GA (2004) Design of Schiff base-like postmetallocene catalytic systems for polymerization of olefins: II. Synthesis of 2, 6-bis(aryliminoalkyl)pyridines with cycloalkyl substituents. Russ J Gen Chem 74:1575–1578
Ionkin AS, Marshall WJ, Adelman DJ, Fones BB, Fish BM, Schiffhauer MF (2008) Modification of iron(II) tridentate bis(imino)pyridine complexes by a boryl group for the production of ?-olefins at high temperature. Organometallics 27:1902–1911
Liu J-Y, Zheng Y, Hu N-H, Li Y-S (2006) Electron effect of p-substituent on iron(II) and cobalt(II) pyridinebisimine catalyst for ethylene polymerization. Chin J Chem 24:1447–1451
Paulino IS, Schuchardt U (2004) A new iron catalyst for ethylene polymerization. J Mol Catal A Chem 211:55–58
Zhilovskii GS, Oleinik II, Ivanchev SS, Tolstikov GA (2009) Design of postmetallocene Schiff base-like catalytic systems for polymerization of olefins: XI. Synthesis of Schiff bases containing cycloalkyl substituents from 2-acetyl-6-bromopyridine. Russ J Org Chem 45:44–47
Toti A, Giambastiani G, Bianchini C, Meli A, Luconi L (2008) New functionalized vinyl monomers by ethylene-(functionalized)-norbornene hetero-trimerization catalyzed by cobalt(II)-(imino)pyridine complexes. Adv Synth Catal 350:1855–1866
Kuwabara J, Takeuchi D, Osakada K (2009) Structures of Co, Pd and Ni complexes with iminopyridine ligands having an hydroxymethyl or acrylate pendant group. Polyhedron 28:2459–2465
Acknowledgment
We thank the Fundação para Ciência e Tecnologia for financial support (Projects PPCDT/QUI/59025/2004, PTDC/QUI/65474/2006 and PTDC/EQU-EQU/110313/2009, co-financed by FEDER) and a postdoctoral fellowship to L.L. (SFRH/BPD/30733/2006).
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2011 Springer Science+Business Media B.V.
About this chapter
Cite this chapter
Li, L., Gomes, P.T. (2011). Oligomerization and Polymerization of Olefins with Iron and Cobalt Catalysts Containing 2,6-Bis(imino)pyridine and Related Ligands. In: CAMPORA, J., GIAMBASTIANI, G. (eds) Olefin Upgrading Catalysis by Nitrogen-based Metal Complexes II. Catalysis by Metal Complexes, vol 36. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-0696-5_3
Download citation
DOI: https://doi.org/10.1007/978-94-007-0696-5_3
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-007-0695-8
Online ISBN: 978-94-007-0696-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)