Oligomerization of Olefins

Chapter
Part of the Lecture Notes in Chemistry book series (LNC, volume 85)

Abstract

This article reviews recent studies on oligomerization of olefins catalyzed by transition metal complexes. Ni, Pd, and Fe complexes, having a ligand with a similar structure to the ethylene polymerization catalyst but with less bulky substituents, convert ethylene to the oligomers as a mixture with various chain lengths with Schulz–Flory molecular weight distribution. Cossee-type insertion of ethylene into the M–C bond and frequent elimination of α-olefins are proposed as the major reaction mechanism. The reaction using the Fe catalyst for polymerization and large excess of chain transfer reagents such as ZnEt2 can yield the oligomers with Poisson distribution. Cr complexes with various ligands promote selective trimerization and/or tetramerization of ethylene to produce 1-hexene and/or 1-octene. The mechanism involving metallacycle is proposed to account for the selectivity. Several Ti and Ta complexes are also effective for the trimerization of ethylene. Oligomerization of α-olefins has been also studied, although the product is frequently composed of branched oligomers and/or inner olefins.

Keywords

Pyrrole Tantalum Trimethylsilyl Pyridyl Et2O 

References

  1. 1.
    Skupińska J (1991) Oligomerization of α-olefins to higher oligomers skupińska. Chem Rev 91:613Google Scholar
  2. 2.
    Dixon JT, Green MJ, Hess FM, Morgan DH (2004) Advances in selective ethylene trimerisation—a critical overview. J Organomet Chem 689:3641Google Scholar
  3. 3.
    Speiser F, Braunstein P, Saussine L (2005) Catalytic ethylene dimerization and oligomerization: recent developments with nickel complexes containing P,N-chelating ligands. Acc Chem Res 38:784Google Scholar
  4. 4.
    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 250:1391Google Scholar
  5. 5.
    Kuhn P, Sémeril D, Matt D, Chetcuti M, Lutz P (2007) Structure-reactivity relationships in SHOP-type complexes: tunable catalysts for the oligomerisation and polymerisation of ethylene. Dalton Trans 515Google Scholar
  6. 6.
    Wass DF (2007) Chromium-catalysed ethene trimerisation and tetramerisation—breaking the rules in olefin oligomerisation. Dalton Trans 816Google Scholar
  7. 7.
    Belov GP (2008) Selective dimerization, oligomerization, homopolymerization and copolymerization of olefins with complex organometallic catalysts. Russ J Appl Chem 81:1655Google Scholar
  8. 8.
    McGuinness D (2009) Alkene oligomerisation and polymerisation with metal-NHC based catalysts. Dalton Trans 6915Google Scholar
  9. 9.
    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 254:431Google Scholar
  10. 10.
    Agapie T (2011) Selective ethylene oligomerization: recent advances in chromium catalysis and mechanistic investigations. Coord Chem Rev 255:861Google Scholar
  11. 11.
    van Leeuwen PWNM, Clément ND, Tschan MJ-L (2011) New processes for the selective production of 1-octenea. Coord Chem Rev 255:1499Google Scholar
  12. 12.
    Kinoshita S, Kawamura K, Fujita T (2011) Early-transition-metal catalysts with phenoxy-Imine-type ligands for the oligomerization of ethylene. Chem Asian J 6:284Google Scholar
  13. 13.
    Schulz GVZ (1935) Highly polymerized compounds CXXII the relation between reaction composition of the reaction product in macropolymerization processes. Phys Chem Abt B 30:379 (1939 43:25)Google Scholar
  14. 14.
    Flory PJ (1940) Molecular size distribution in ethylene oxide polymers. J Am Chem Soc 62:1561Google Scholar
  15. 15.
    Whyman R (2001) Olefin oligomerization and polymerization. Applied organometallic chemistry and catalysis, chap. 6. Oxford Press, Oxford Google Scholar
  16. 16.
    Peuckert M, Keim W (1983) A new nickel complex for the oligomerization of ethylene. Organometallics 2:594Google Scholar
  17. 17.
    Kuhn P, Sémeril D, Jeunesse C, Matt D, Neuburger M, Mota A (2006) Ethylene oligomerisation and polymerisation with nickel phosphanylenolates bearing electron-withdrawing substituetns: structure—reactivity relationships. Chem Eur J 12:5210Google Scholar
  18. 18.
    Malinoski JM, Brookhart M (2003) Polymerization and oligomerization of ethylene by cationic nickel(II) and palladium(II) complexes containing bidentate phenacyldiarylphosphine ligands. Organometallics 22:5324Google Scholar
  19. 19.
    Komon ZJA, Bu X, Bazan GC (2000) Synthesis, characterization, and ethylene oligomerization acting of [(C5H5)2PC6H4C(O-B(C6F5)3O-κ2 P,O)Ni(η 3-CH2C6H5). J Am Chem Soc 122:12379Google Scholar
  20. 20.
    Svejda SA, Brookhart M (1999) Ethylene oligomerization and propylene dimerization using cationic (α-Diimine)Nickel(II) catalysts. Organometallics 18:65Google Scholar
  21. 21.
    Killian CM, Johnson LK, Brookhart M (1997) Preparation of linear a-Olefins using cationic nickel(II) α-Diimine catalysts. Organometallics 16:2005Google Scholar
  22. 22.
    Conley MP, Burns CT, Jordan RF (2007) Mechanism of ethylene oligomerization by a cationic palladium(II) alkyl complex that contains a (3,5-Me2-pyrazolyl)2CHSi(p-tolyl)3) ligand. Organometallics 26:6750Google Scholar
  23. 23.
    Salo EV, Guan Z (2003) Late-transition-metal complexes with bisazaferrocene ligands for ethylene oligomerization. Organometallics 22:5033Google Scholar
  24. 24.
    Yu J, Hu X, Zeng Y, Zhang L, Ni C, Hao X, Sun W-H (2011) Synthesis, characterisation and ethylene oligomerisation behaviour of N-(2-substituted-5,6,7-trihydroquinolin-8-ylidene)arylaminonickel dichlorides. New J Chem 35:178Google Scholar
  25. 25.
    Spencer LP, Altwer R, Wei P, Gelmini L, Gauld J, Stephan DW (2003) Pyridine—and Imidazole—Phosphinimine bidentate ligand complexes: considerations for ethylene oligomerization catalysts. Organometallics 22:3841Google Scholar
  26. 26.
    Chen H-P, Liu Y-H, Peng S-M, Liu S-T (2003) New bulky Phosphino—pyridine ligands. palladium and nickel complexes for the catalytic polymerization and oligomerization of ethylene. Organometallics 22:4893Google Scholar
  27. 27.
    Flapper J, Kooijman H, Lutz M, Spek AL, van Leeuwen PWNM, Elsevier CJ, Kamer PCJ (2009) Nickel and palladium complexes of pyridine—phosphine ligands as ethene oligomerization catalysts. Organometallics 28:1180Google Scholar
  28. 28.
    Flapper J, van Leeuwen PWNM, Elsevier CJ, Kamer PCJ (2009) Nickel and palladium complexes of pyridine—phosphine ligands bearing aromatic substituents and their behavior as catalysts in ethene oligomerization. Organometallics 28:3264Google Scholar
  29. 29.
    Flapper J, Kooijman H, Lutz M, Spek AL, van Leeuwen PWNM, Elsevier CJ, Kamer PCJ (2009) Nickel and palladium complexes of new pyridine—phosphine ligands and their use in ethene oligomerization. Organometallics 28:3272Google Scholar
  30. 30.
    Dyer PW, Fawcett J, Hanton MJ (2008) Rigid N-Phosphino guanidine P,N ligands and their use in nickel-catalyzed oligomerization. Organometallics 27:5082Google Scholar
  31. 31.
    Daugulis O, Brookhart M, White PS (2002) Phosphinidine—palladium complexes for the polymerization and oligomerization of ethylene. Organometallics 21:5935Google Scholar
  32. 32.
    Doherty MD, Trudeau S, White PS, Morken JP, Brookhart M (2007) Ethylene oligomerization catalyzed by a unique phosphine—oxazoline palladium(II) complex. propagation and chain transfer mechanisms. Organometallics 26:1261Google Scholar
  33. 33.
    Speiser F, Braunstein P, Saussine L, Welter R (2004) Nickel complexes with oxazoline-based P,N-chelate ligands: syntehsis, structures, and catalytic ethylene oligomerization behavior. Organometallics 23:2613Google Scholar
  34. 34.
    Speiser F, Braunstein P, Saussine L (2004) New nickel ethylene oligomerization catalysts bearing bidentate P,N-phosphinopyridine ligands with different substitutents to phosphorus. Organometallics 23:2625Google Scholar
  35. 35.
    Speiser F, Braunstein P, Saussine L (2004) Nickel complexes bearing new P,N-phosphinopyridine ligands for the catalytic oligomerization of ethylene. Organometallics 23:2633Google Scholar
  36. 36.
    Kermagoret A, Braunstein P (2008) Mono- and dinuclear nickel complexes with phosphino-, phosphinito-, and phosphonitopyridine ligands: synthesis, structures, and catalytic oligomerization of ethylene. Organometallics 27:88Google Scholar
  37. 37.
    Chavez P, Rios IG, Kermagoret A, Pattacini R, Meli A, Bianchini C, Giambastiani G, Braunstein P (2009) Nickel complexes with phosphinito-oxazoline ligands: temperature-controlled formation of mono- or dinuclear complexes and catalytic oligomerization of ethylene and propylene. Organometallics 28:1776Google Scholar
  38. 38.
    Zhang S, Pattacini R, Jie S, Braunstein P (2012) A phosphino-oxazoline ligand as a P,N-bridge in palladium/cobalt or P,N-chelate in nickel complexes: catalytic ethylene oligomerization. Dalton Trans 41:379Google Scholar
  39. 39.
    Weng Z, Teo S, Koh LL, Hor TSA (2005) Ethylene oligomerization at coordinatively and electronically unsaturated low-valent nickel. Angew Chem Int Ed 44:7560Google Scholar
  40. 40.
    Jie S, Zhang S, Sun W-H (2007) 2-Arylimino-9-phenyl-1, 10-phenanthrolinyl-iron, -cobalt and -nickel complexes: synthesis, characterization and ethylene oligomerizaiton behavior. Eur J Inorg Chem 5584Google Scholar
  41. 41.
    Gao R, Zhang M, Liang T, Wang F, Sun W-H (2008) Nickel(II) complexes chelated by 2-arylimino-6-benzoxazolylpyridine: synthesis, characterization, and ethylene oligomerization. Organometallics 27:5641Google Scholar
  42. 42.
    Chen X, Zhang L, Yu J, Hao X, Liu H, Sun W-H (2011) Synthesis, characterization and ethylene oligomerization behavior of 2-(Chloro-substituted-1h-benzoimidazol-2-yl)-6-(1-aryliminoethyl)pyridylnickel dihalides. Inorg Chim Acta 370:156Google Scholar
  43. 43.
    Liu H, Zhang L, Chen L, Redshaw C, Li Y, Sun W-H (2011) Synthesis, characterization and ethylene oligomerization behavior of 2-benzoimidazol-8-ethoxyquinolylnickel dihalides. Dalton Trans 40:2614Google Scholar
  44. 44.
    Hou J, Sun W-H, Zhang S, Ma H, Deng Y, Lu X (2006) Synthesis and characterization of tridentate nickel complexes bearing P^N^N and P^N^P ligands and their catalytic properties in ethylene oligomerization. Organometallics 25:236Google Scholar
  45. 45.
    Shi P-Y, Liu Y-H, Peng S-M, Liu S-T (2002) Palladium(II) complexes containing P~N~O donors. Ligand effect of tridentate versus bidentate coordination on the oligomerization of ethylene. Organometallics 21:3203Google Scholar
  46. 46.
    Zhang C, Sun W-H, Wang Z-X (2006) Cobalt and nickel complexes bearing pyrazolyliminophosphorane ligands: synthesis, characterisation and catalytic ethylene oligomerisation behavior. Eur J Inorg Chem 4895Google Scholar
  47. 47.
    Sun W-H, Hao P, Zhang S, Shi Q, Zuo W, Tang X (2007) Iron(II) and cobalt(II) 2-(benzimidazolyl)-6-(1-(arylimino)ethyl)pyridyl complexes as catalysts for ethylene oligomerization and polymerization. Organometallics 26:2720Google Scholar
  48. 48.
    Bianchini C, Mantovani G, Meli A, Migliacci F, Laschi F (2003) Selective oligomerization of ethylene to linear a-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 22:2545Google Scholar
  49. 49.
    Small BL, Brookhart M (1998) Iron-based catalysts with exceptionally high activities and selectivities for oligomerization of ethylene to linear α-olefins. J Am Chem Soc 120:7143Google Scholar
  50. 50.
    Britovsek 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 6:2221Google Scholar
  51. 51.
    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 22:4312Google Scholar
  52. 52.
    Chen Y, Qian C, Sun J (2003) Fluoro-substituted 2,6-Bis(imino)pyridyl iron and cobalt complexes: high-activity ethylene oligomerization catalysts. Organometallics 22:1231Google Scholar
  53. 53.
    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 C1-symmetric [2,6-Bis(arylimino)pyridyl]iron dichloride precursor. Organometallics 23:6087Google Scholar
  54. 54.
    Bianchini C, Mantovani G, Meli A, Migliacci F, Zanobini F, Laschi F, Sommazzi A (2003) Oligomerization of ethylene to lnear a-olefins by new Cs- and C1-symmetric [2,6-Bis(imino)pyridyl]iron and –cobalt dichloride complexes. Eur J Inorg Chem 1620Google Scholar
  55. 55.
    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 25:666Google Scholar
  56. 56.
    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 28:2225Google Scholar
  57. 57.
    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 309:166Google Scholar
  58. 58.
    Zhang M, Hao P, Zuo W, Jie S, Sun W-H (2008) 2-(Benzimidazolyl)-1,10-phenanthrolyl metal (Fe and Co) complexes and their catalytic behaviors toward ethylene oligomerization. J Organomet Chem 693:483Google Scholar
  59. 59.
    Wang K, Wedeking K, Zuo W, Zhang D, Sun W-H (2008) Iron(II) and cobalt(II) complexes bearing N-((pyridine-2-yl)methylene)-quinolin-8-amine derivatives: synthesis and application to ethylene oligomerization. J Organomet Chem 693:1073Google Scholar
  60. 60.
    Boudier A, Breuil P-AR, Magna L, Rangheard C, Ponthus J, Olivier-Bourbigou H, Braunstein P (2011) Novel catalytic system for ethylene oligomerization: an iron(III) complex with an anionic N,N,N ligand. Organometallics 30:2640Google Scholar
  61. 61.
    Tenza K, Hanton MJ, Slawin AMZ (2009) Ethylene oligomerization using first-row transition metal complexes featuring heterocyclic variants of bis(imino)pyridine ligands. Organometallics 28:4852Google Scholar
  62. 62.
    Small BL, Rios R, Fernandez ER, Carney MJ (2007) Oligomerization of ethylene using new iron catalysts bearing pendant donor modified α-diimine ligands. Organometallics 26:1744Google Scholar
  63. 63.
    Small BL, Rios R, Fernandez ER, Gerlach DL, Halfen JA, Carney MJ (2010) Oligomerization of ethylene using new tridentate iron catalysts bearing α-diimine ligands with pendant S and P donors. Organometallics 29:6723Google Scholar
  64. 64.
    Zhang W, Sun W-H, Hou J, Wedeking K, Schultz S, Fröhlich R, Song H (2006) Synthesis, characterization, and ethylene oligomerization and polymerization of [2,6-Bis(2-benzimidazolyl)pyridyl]chromium chlorides. Organometallics 25:1961Google Scholar
  65. 65.
    Zhang S, Jie S, Shi Q, Sun W-H (2007) Chromium(III) complexes bearing 2-imino-1,10-phenanthrolines: synthesis, molecular structures and ethylene oligomerization and polymerization. J Mol Catal A: Chem 276:174Google Scholar
  66. 66.
    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 37:4375Google Scholar
  67. 67.
    Chen Y, Zuo W, Hao P, Zhang S, Gao K, Sun W-H (2008) Chromium(III) complexes ligated by 2-(1-isopropyl-2-benzimidazolyl)-6-(1-(arylimino)ethyl) pyridines: synthesis, characterization and their ethylene oligomerization and polymerization. J Organomet Chem 693:750Google Scholar
  68. 68.
    Xiao L, Zhang M, Sun W-H (2010) Synthesis, characterization and ethylene oligomerization and polymerization of 2-(1H-2-benzimidazolyl)-6-(1-(arylimino)ethyl)pyridylchromium chlorides. Polyhedron 29:142Google Scholar
  69. 69.
    Gao R, Liang T, Wang F, Sun W-H (2009) Chromium(III) complexes bearing 2-benzoxazolyl-6-arylimino-pyridines: synthesis and their ethylene reactivity. J Organomet Chem 694:3701Google Scholar
  70. 70.
    Zhang M, Wang K, Sun W-H (2009) Chromium(III) complexes bearing 2-benzazole-1,10-phenanthrolines: synthesis, molecular structures and ethylene oligomerization and polymerization. Dalton Trans 6354Google Scholar
  71. 71.
    McGuinness DS, Gibson VC, Wass DF, Steed JW (2003) Bis(carbine)pyridine complexes of Cr(III): exceptionally active catalysts for the oligomerization of ethylene. J Am Chem Soc 125:12716Google Scholar
  72. 72.
    McGuinness DS, Gibson VC, Steed JW (2004) Bis(carbine)pyridine complexes of the early to middle transition metals: survey of ethylene oligomerization and polymerization capability. Organometallics 23:6288Google Scholar
  73. 73.
    McGuinness DS, Suttil JA, Gardiner MG, Davies NW (2008) Ethylene oligomerization with Cr-NHC catalysts: further insights into the extended metallacycle mechanism of chain growth. Organometallics 27:4238Google Scholar
  74. 74.
    Kirillov E, Roisnel T, Razavi A, Carpentier J-F (2009) Chromium(III) complexes of sterically crowded bidentate {ONR} and tridentate {ONNR} naphthoxy-imine ligands: syntheses, structures, and use in ethylene oligomerization. Organometallics 28:2401Google Scholar
  75. 75.
    Britovsek GJP, Cohen SA, Gibson VC, Maddox PJ, van Meurs M (2002) Iron-catalyzed polyethylene chain growth on zinc: linear α-olefins with a Poisson distribution. Angew Chem Int Ed 41:489Google Scholar
  76. 76.
    Hessen B, van der Heijden H (1996) Homologation of α-olefins with ethene by a neutral zirconium alkyl complex. J Am Chem Soc 118:11670Google Scholar
  77. 77.
    Manyik RM, Walker WE, Wilson TP (1977) A soluble chromium-based catalyst for ethylene trimerization and polymerization. J Catal 47:197Google Scholar
  78. 78.
    Briggs JR (1989) The selective trimerization of ethylene to hex-1-ene. J Chem Soc Chem Commun 674Google Scholar
  79. 79.
    Emrich R, Heinemann O, Jolly PW, Krüger C, Verhovnik GPJ (1997) The role of metallacycles in the chromium-catalyzed trimerization of ethylene. Organometallics 16:1511Google Scholar
  80. 80.
    van Rensburg WJ, Grové C, Steynberg JP, Stark KB, Huyser JJ, Steynberg PJ (2004) A DFT study toward the mechanism of chromium-catalyzed ethylene trimerization. Organometallics 23:1207Google Scholar
  81. 81.
    Bhaduri S, Mukhopadhyay S, Kulkarni SA (2009) Density functional studies on chromium catalyzed ethylene trimerization. J Organomet Chem 694:1297Google Scholar
  82. 82.
    Carter A, Cohen SA, Cooley NA, Murphy A, Scutt J, Wass DF (2002) High activity ethylene trimerisation catalysts based on diphosphine ligands. Chem Commun 858Google Scholar
  83. 83.
    Blann K, Bollmann A, Dixon JT, Hess FM, Killian E, Maumela H, Morgan DH, Neveling A, Otto S, Overett MJ (2005) Highly selective chromium-based ethylene trimerisation catalysts with bulky diphosphinoamine ligands. Chem Commun 620 Google Scholar
  84. 84.
    Agapie T, Schofer SJ, Labinger JA, Bercaw JE (2004) Mechanistic studies of the ethylene trimerization reaction with chromium—diphosphine catalysts: experimental evidence for a mechanism involving metallacyclic intermediates. J Am Chem Soc 126:1304Google Scholar
  85. 85.
    Agapie T, Labinger JA, Bercaw JE (2007) Mechanistic studies of olefin and alkyne trimerization with chromium catalysts: deuterium labeling and studies of regiochemistry using a model chromacyclopentane complex. J Am Chem Soc 129:14281Google Scholar
  86. 86.
    Agapie T, Day MW, Henling LM, Labinger JA, Bercaw JE (2006) A chromium-diphosphine system for catalytic ethylene trimerization: synthetic and structural studies of chromium complexes with a nitrogen-bridged diphosphine ligand with ortho-methoxyaryl substituetns. Organometallics 25:2733Google Scholar
  87. 87.
    Schofer SJ, Day MW, Henling LM, Labinger JA, Bercaw JE (2006) Ethylene trimerization catalysts based on chromium complexes with a nitrogen-bridged diphosphine ligand having ortho-methoxyaryl or ortho-thiomethoxy substituents: well-defined catalyst precursors and investigations of the mechanism. Organometallics 25:2743Google Scholar
  88. 88.
    Bowen LE, Haddow MF, Orpen AG, Wass DF (2007) One electron oxidation of chromium n,n-bis(diarylphosphino)amine and bis(diarylphosphino)methane complexes relevant to ethene trimerisation and tetramerisation. Dalton Trans 1160Google Scholar
  89. 89.
    Aluri BR, Peulecke N, Peitz S, Spannenberg A, Müller BH, Schulz S, Drexler H-J, Heller D, Al-Hazmi MH, Mosa FM, Wöhl A, Müller W, Rosenthal U (2010) Coordination Coordination chemistry of new selective ethylene trimerisation ligand Ph2PN(iPr)P(Ph)NH(R) (R = iPr, Et) and tests in catalysis. Dalton Trans 39:7911Google Scholar
  90. 90.
    Wöhl A, Müller W, Peitz S, Peulecke N, Aluri BR, Müller BH, Heller D, Rosenthal U, Al-Hazmi MH, Mosa FM (2010) Influence of process parameters on the reaction kinetics of the chromium-catalyzed trimerization of ethylene. Chem Eur J 16:7833Google Scholar
  91. 91.
    Müller BH, Peulecke N, Peitz S, Aluri BR, Rosenthal U, Al-Hazmi MH, Mosa FM, Wöhl A, Müller W (2011) Activity enhancement of a catalyst system for the selective trimerization of ethene to 1-hexene by modification of the chromium to chloride to aluminium ratio. Chem Eur J 17:6935Google Scholar
  92. 92.
    Klemps C, Payet E, Magna L, Saussine L, Le Goff XF, Le Floch P (2009) PCNCP ligands in the chromium-catalyzed oligomerization of ethyene: tri- versus tetramerization. Chem Eur J 15:8259Google Scholar
  93. 93.
    McGuinness DS, Wasserscheid P, Keim W, Hu C, Englert U, Dixon JT, Grove C (2003) Novel Cr-PNP complexes as catalysts for the trimerisation of ethylene. Chem Commun 2003:334Google Scholar
  94. 94.
    McGuinness DS, Wasserscheid P, Keim W, Morgan D, Dixon JT, Bollmann A, Maumela H, Hess F, Englert U (2003) First Cr(III)—SNS complexes and their use as highly efficient catalysts for the trimerization of ethylene to 1-hexene. J Am Chem Soc 125:5272Google Scholar
  95. 95.
    Jabri A, Temple C, Crewdson P, Gambarotta S, Korobkov I, Duchateau R (2006) Role of the metal oxidation state in the sns—cr catalyst for ethylene trimerization: isolation of di- and trivalent cationic intermediates. J Am Chem Soc 128:9238Google Scholar
  96. 96.
    Temple CN, Jabri A, Crewdson P, Gambarotta S, Korobkov I, Duchateau R (2006) The question of the Cr oxidation state in the {Cr(SNS)} catalyst for selective ethylene trimerization: an unanticipated re-oxidation pathway. Angew Chem Int Ed 45:7050Google Scholar
  97. 97.
    Temple CN, Gambarotta S, Korobkov I, Duchateau R (2007) New insight into the role of the metal oxidation state in controlling the selectivity of the Cr-(SNS) ethylene trimerization catalyst. Organometallics 26:4598Google Scholar
  98. 98.
    McGuinness DS, Wasserscheid P, Morgan DH, Dixon JT (2005) Ethylene trimerization with mixed-donor ligand (N,P,S) chromium complexes: effect of ligand structure on activity and selectivity. Organometallics 24:552Google Scholar
  99. 99.
    McGuinness DS, Brown DB, Tooze RP, Hess FM, Dixon JT, Slawin MZ (2006) Ethylene trimerization with Cr—PNP and Cr—SNS complexes: effect of ligand structure, metal oxidation state, and role of activator on catalysis. Organometallics 25:3605Google Scholar
  100. 100.
    Bluhm ME, Walter O, Döring M (2005) Chromium imine and amine complexes as homogeneous catalysts for the trimerisation and polymerisation of ethylene. J Organomet Chem 690:713Google Scholar
  101. 101.
    Zhang J, Braunstein P, Hor TSA (2008) Highly selective chromium(III) ethylene trimerization catalysts with [NON] and [NSN] heteroscorpionate ligands. Organometallics 27:4277Google Scholar
  102. 102.
    Zhang J, Li A, Hor TSA (2009) Ligand effect on ethylene trimerisation with [NNN]-heteroscorpionate pyrazolyl Cr(III) catalysts. Dalton Trans 9327Google Scholar
  103. 103.
    Zhang J, Li A, Hor TSA (2009) Crystallographic revelation of the role of alme3 (in mao) in cr [NNN] pyrazolyl catalyzed ethylene trimerization. Organometallics 28:2935Google Scholar
  104. 104.
    Kilpatrick AFR, Kulangara SV, Cushion MG, Duchateau R, Mountford P (2010) Synthesis and ethylene trimerisation capability of new chromium(II) and chromium(III) heteroscorpionate complexes. Dalton Trans 39:3653Google Scholar
  105. 105.
    Albahily K, Al-Baldawi D, Gambarotta S, Duchateau R, Koç E, Burchell TJ (2008) Preparation and characterization of a switchable singel-component chromium trimerization catalyst. Organometallics 27:5708Google Scholar
  106. 106.
    Albahily K, Al-Baldawi D, Gambarotta S, Koç E, Duchateau R (2008) Isolation of a chromium hydride single-component ethylene polymerization catalyst. Organometallics 27:5943Google Scholar
  107. 107.
    Albahily K, Fomitcheva V, Gambarotta S, Korobkov I, Murugesu M, Gorelsky SI (2011) Preparation and characterization of a reduced chromium complex via vinyl oxidative coupling: formation of a self-activating catalyst for selective ethylene trimerization. J Am Chem Soc 133:6380Google Scholar
  108. 108.
    Thapa I, Gambarotta S, Korobkov I, Murugesu M, Budzelaar P (2012) Isolation and characterization of a class II mixed-valence chromium(I)/(II) self-activating ethylene trimerization catalyst. Organometallics 31:486Google Scholar
  109. 109.
    Vidyaratne I, Nikiforov GB, Gorelsky SI, Gambarotta S, Duchateau R, Korobkov I (2009) Isolation of a self-activating ethylene trimerization catalyst. Angew Chem Int Ed 48:6552Google Scholar
  110. 110.
    Deckers PJW, Hessen B, Teuben JH (2001) Switching a catalyst system from ethene polymerization to ethene trimerization with a hemilabile ancillary ligand. Angew Chem Int Ed 40:2516Google Scholar
  111. 111.
    Deckers PJW, Hessen B, Teuben JH (2002) Catalytic trimerization of ethene with highly active cyclopentadienyl—arene titanium catalysts. Organometallics 21:5122Google Scholar
  112. 112.
    Often E, Batinas AA, Meetsma A, Hessen B (2009) Versatile coordination of cyclopentadienyl-arene ligands and its role in titanium—catalyzed ethylene trimerization. J Am Chem Soc 131:5298Google Scholar
  113. 113.
    Huang J, Wu T, Qian Y (2003) Ethylene trimerization with a half-sandwich titanium complex bearing a pendant thienyl group. Chem Commun 2816Google Scholar
  114. 114.
    Wu T, Qian Y, Huang J (2004) Catalytic trimerization of ethylene by half-sandwich titanium complexes bearing a pendant ethereal group. J Mol Catal A: Chem 214:227Google Scholar
  115. 115.
    Hagen H, Kretschmer WP, van Buren FR, Hessen B, van Oeffelen DA (2006) Selective ethylene trimerization: a study into the mechanism and the reduction of PE formation. J Mol Catal A: Chem 248:237Google Scholar
  116. 116.
    Blok ANJ, Budzelaar PHM, Gal AW (2003) Mechanism of ethene trimerization at an ansa-(arene)(cyclopentadienyl) titanium fragment. Organometallics 22:2564Google Scholar
  117. 117.
    de Bruin TJM, Magna L, Raybaud P, Toulhoat H (2003) Hemilablile ligand induced selectivity: a DFT study on ethylene trimerization catalyzed by titanium complexes. Organometallics 22:3404Google Scholar
  118. 118.
    Tobisch S, Ziegler T (2003) Catalytic linear oligomerization of ethylene to higher a-olefins: insight into the origin of the selective generation of 1-hexene promoted by a cationic cyclopentadienyl-arene titanium active catalyst. Organometallics 22:5392Google Scholar
  119. 119.
    Tobisch S, Ziegler T (2004) Catalytic oligomerization of ethylene to higher linear a-olefins promoted by cationic group 4 cyclopentadienyl-arene active catalysts: a DFT investigation exploring the influence of electronic factors on the catalytic properties by modification of the hemilabile arene functionality. Organometallics 23:4077Google Scholar
  120. 120.
    Tobisch S, Ziegler T (2004) Catalytic oligomerization of ethylene to higher linear a-olefins promoted by the cationic group 4 [(h5-Cp-(CMe2-bridge)-Ph)MII(ethylene)2]+ (M = Ti, Zr, Hf) active catalysts: a density functional investigation of the influence of the metal on the catalytic activity and selectivity. J Am Chem Soc 126:9059Google Scholar
  121. 121.
    Tobisch S, Ziegler T (2005) Catalytic oligomerization of ethylene to higher linear a-olefins promoted by cationic group 4 cyclopentadienyl-arene active catalysts: toward the computational design of zirconium- and hafnium-based ethylene trimerization catalysts. Organometallics 24:256Google Scholar
  122. 122.
    Suzuki Y, Kinoshita S, Shibahara A, Ishii S, Kawamura K, Inoue Y, Fujita T (2010) Trimerization of ethylene to 1-hexene with titanium complexes bearing phenoxy—imine ligands with pendant donors combined with MAO. Organometallics 29:2394Google Scholar
  123. 123.
    Andes C, Harkins SB, Murtuza S, Oyler K, Sen A (2001) New tantalum-based catalyst system for the selective trimerization of ethene to 1-hexene. J Am Chem Soc 123:7423Google Scholar
  124. 124.
    Yu Z-X, Houk KN (2003) Why trimerization? computational elucidation of the origin of selective trimerization of ethene catalyzed by [TaCl3(CH3)2] and an agostic assisted hydride transfer mechanism. Angew Chem Int Ed 42:808Google Scholar
  125. 125.
    Arteaga-Müller R, Tsurugi H, Saito T, Yanagawa M, Oda S, Mashima K (2009) New tantalum ligand-free catalyst system for highly selective trimerization of ethylene affording 1-hexene: new evidence of a metallacycle mechanism. J Am Chem Soc 131:5370Google Scholar
  126. 126.
    Kondo T, Yamamoto K, Takagi D, Shen L, Yoshida Y, Kimura Y, Toshimitsu A, Kuramoto M, Shiraki Y (2010) Selective trimerization of ethylene to isohexenes catalyzed by a ruthenium(0) complex. Chem Cat Chem 2:1565Google Scholar
  127. 127.
    Bollmann A, Blann K, Dixon JT, Hess F, Killian E, Maumela H, McGuinness DS, Morgan DH, Neveling A, Otto S, Overett M, Slawin AMZ, Wasserscheid P, Kuhlmann S (2004) Ethylene tetramerization: a new route to produce 1-octene in exceptionally high selectivites. J Am Chem Soc 126:14712Google Scholar
  128. 128.
    Overett MJ, Blann K, Bollmann A, Dixon JT, Hess FM, Killian E, Maumela H, Morgan DH, Neveling A, Otto S (2005) Ethylene trimerisation and tetramerisation catalysts with polar-substituted diphosphinoamine ligands. Chem Commun 622Google Scholar
  129. 129.
    Blann K, Bollmann A, de Bod H, Dixon JT, Killian E, Nongodlwana P, Maumela MC, Maumela H, McConnell AE, Morgan DH, Overett M, Prétorius M, Kuhlmann S, Wasserscheid P (2007) Ethylene tetramerisation: subtle effects exhibited by N-substituted diphosphinoamine ligands. J Catal 249:244Google Scholar
  130. 130.
    Kuhlmann S, Blann K, Bollmann A, Dixon JT, Killian E, Maumela MC, Maumela H, Morgan DH, Prétorius M, Taccardi N, Wasserscheid P (2007) N-substituted diphosphinoamines: toward rational ligand design for the efficient tetramerization of ethylene. J Catal 245:279Google Scholar
  131. 131.
    Killian E, Blann K, Bollmann A, Dixon JT, Kuhlmann S, Maumela MC, Maumela H, Morgan DH, Nongodlwana P, Overett MJ, Prétorius M, Höfener K, Wasserscheid P (2007) The use of Bis(diphenylphosphino)amines with N-aryl functionalities in selective ethylene tri- and tetramerisation. J Mol Catal A: Chem 270:214Google Scholar
  132. 132.
    Elowe PR, McCann C, Pringle PG, Spitzmesser SK, Bercaw JE (2006) Nitrogen-linked diphosphine ligands with ethers attached to nitrogen for chromium-catalyzed ethylene tri- and tetramerization. Organometallics 25:5255Google Scholar
  133. 133.
    Weng Z, Teo S, Hor TSA (2007) Chromium(III) catalysed ethylene tetramerization promoted by Bis(phosphino)amines with an N-functionalized pendant. Dalton Trans 3493Google Scholar
  134. 134.
    Overett MJ, Blann K, Bollmann A, de Villiers R, Dixon JT, Killian E, Maumela MC, Maumela H, McGuinness DS, Morgan DH, Rucklidge A, Slawin AMZ (2008) Carbon-bridged diphosphine ligands for chromium-catalyzed ethylene tetramerisation and trimerisation reactions. J Mol Catal A: Chem 283:114Google Scholar
  135. 135.
    Kim S-K, Kim T-J, Chung J-H, Hahn T-K, Chae S-S, Lee H-S, Cheong M, Kang SO (2010) Bimetallic ethylene tetramerization catalysts derived from chiral DPPDME ligands: syntheses, structural characterizations, and catalytic performance of [(DPPDME)CrCl3]2 (DPPDME = S,S- and R,R-chiraphos and meso-achiraphos). Organometallics 29:5805Google Scholar
  136. 136.
    Dulai A, de Bod H, Hanton MJ, Smith DM, Downing S, Mansell SM, Wass DF (2009) C-substituted Bis(diphenylphosphino)methane-type ligands for chromium-catalyzed selective ethylene oligomerization reactions. Organometallics 28:4613Google Scholar
  137. 137.
    Rucklidge AJ, McGuinness DS, Tooze RP, Slawin AMZ, Pelletier JDA, Hanton MJ, Webb PB (2007) Ethylene tetramerization with cationic chromium(I) complexes. Organometallics 26:2782Google Scholar
  138. 138.
    McGuinness DS, Rucklidge AJ, Tooze RP, Slawin AMZ (2007) Cocatalyst influence in selective oligomerization: effect on activity, catalyst stability, and 1-hexene/1-octene selectivity in the ethylene trimerization and tetramerization reaction. Organometallics 26:2561Google Scholar
  139. 139.
    McGuinness DS, Overett M, Tooze RP, Blann K, Dixon JT, Slawin AMZ (2007) Ethylene tri- and tetramerization with borate cocatalysts: effects on activity, selectivity, and catalyst degradation pathways. Organometallics 26:1108Google Scholar
  140. 140.
    Jiang T, Ning Y, Zhang B, Li J, Wang G, Yi J, Huang Q (2006) Preparation of 1-octene by the selective tetramerization of ethylene. J Mol Catal A: Chem 259:161Google Scholar
  141. 141.
    Chen H, Liu X, Hu W, Ning Y, Jiang T (2007) Effects of halide in homogeneous Cr(III)/PNP/MAO catalytic systems for ethylene tetramerization toward 1-octene. J Mol Catal A: Chem 270:273Google Scholar
  142. 142.
    Overett MJ, Blann K, Bollmann A, Dixon JT, Haasbroek D, Killian E, Maumela H, McGuinness DS, Morgan DH (2005) Mechanistic investigations of the ethylene tetramerisation reaction. J Am Chem Soc 127:10723Google Scholar
  143. 143.
    Jabri A, Crewdson P, Gambarotta S, Korobkov I, Duchateau R (2006) Isolation of a cationic chromium(II) species in a catalytic system for ethylene tri- and tetramerization. Organometallics 25:715Google Scholar
  144. 144.
    Wöhl A, Müller W, Peulecke N, Müller BH, Peitz S, Heller D, Rosenthal U (2009) Reaction kinetics of the ethene tetramerization catalyst system CrCl3(THF)3, Ph2PN(iPr)PPh2 and MAO: the unexpected and unusual formation of odd-numbered 1-olefins. J Mol Catal A: Chem 297:1Google Scholar
  145. 145.
    Peitz S, Aluri BR, Peulecke N, Müller BH, Wöhl A, Müller W, Al-Hazmi MH, Mosa FM, Rosenthal U (2010) An alternative mechanistic concept for homogeneous selective ethylene oligomerization of chromium-based catalysts: binuclear metallacycles as a reason for 1-octene selectivity? Chem Eur J 16:7670Google Scholar
  146. 146.
    Christoffers J, Bergman RG (1996) Catalytic dimerization reactions of α-olefins and α,ω-dienes with Cp2ZrCl2/poly(methylalumoxane): formation of dimers, carbocycles, and oligomers. J Am Chem Soc 118:4715Google Scholar
  147. 147.
    Keim W, Hoffmann B, Lodewick R, Peuckert M, Schmitt G (1979) Linear oligomerization of olefins via nickel chelate complexes and mechanistic considerations based on semi-empirical calculations. J Mol Catal 6:79Google Scholar
  148. 148.
    Beach DL, Bozik JE, Wu C-Y, Kissin YV (1986) Linear dimerization of propylene and 1-butene catalyzed by (η 3-4-cyclooctene-1-yl)(1,1,1,5,5,5-hexafluoro-2,4-pentanedionato)nickel. J Mol Catal 34:345Google Scholar
  149. 149.
    Ellis B, Keim W, Wasserscheid P (1999) Linear dimerisation of but-1-ene in biphasic mode using buffered chloroaluminate ionic liquid solvents. Chem Commun 337Google Scholar
  150. 150.
    Small BL, Marcucci AJ (2001) Iron catalysts for the head-to-head dimerization of a-olefins and mechanistic implications for the production of linear α-olefins. Organometallics 20:5738Google Scholar
  151. 151.
    Small BL (2003) Tridentate cobalt catalysts for linear dimerization and isomerization of α-olefins. Organometallics 22:3178Google Scholar
  152. 152.
    Tellmann KP, Gibson VC, White AJP, Williams DJ (2005) Selective dimerization/oligomerization of α-olefins by cobalt bis(imino)pyridine catalysts stabilized by trifluoromethyl substituents: group 9 metal catalysts with productivities matching those of iron systems. Organometallics 24:280Google Scholar
  153. 153.
    Broene RD, Brookhart M, Lamanna WM, Volpe AF Jr (2005) Cobalt-catalyzed dimerization of α-olefins to give linear α-olefin products. J Am Chem Soc 127:17194Google Scholar
  154. 154.
    McLain SJ, Sancho J, Schrock RR (1980) Selective dimerization of monosubstituted α-olefins by tantalacyclopentane catalysts. J Am Chem Soc 102:5610Google Scholar
  155. 155.
    Köhn RD, Haufe M, Kociok-Köhn G, Grimm S, Wasserscheid P, Keim W (2000) Selective trimerization of α-olefins with triazacyclohexane complexes of chromium as catalysts. Angew Chem Int Ed 39:4337Google Scholar
  156. 156.
    Wassercheid P, Grimm S, Köhn RD, Haufe M (2001) Synthesis of synthetic lubricants by trimerization of 1-decene and 1-dodecene with homogeneous chromium catalysts. Adv Synth Catal 343:814Google Scholar
  157. 157.
    RajanBabu TV (2009) In pursuit of an ideal carbon-carbon bond-forming reaction: development and applications of the hydrovinylation of olefins. Synlett 853Google Scholar
  158. 158.
    Hilt G (2012) Hydrovinylation reactions—atom-economic transformations with steadily increasing synthetic potential. Eur J Org Chem 4441Google Scholar
  159. 159.
    RajanBabu TV (2003) Asymmetric hydrovinylation. Chem Rev 103:2845Google Scholar
  160. 160.
    Ura Y, Tsujita H, Mitsudo T, Kondo T (2007) Ruthenium-complex-catalyzed highly selective co-oligomerization of alkenes. Bull Korean Chem Soc 28:2139Google Scholar
  161. 161.
    Ura Y, Tsujita H, Wada K, Kondo T, Mitsudo T (2005) Ruthenium-complex-catalyzed regio- and stereoselective linear codimerization of 2-norbornenes with acrylic compounds. J Org Chem 70:6623Google Scholar
  162. 162.
    Tsujita H, Ura Y, Matsuki S, Wada K,Kondo T, Mitsudo T (2007) Regio- and stereoselective synthesis of enamides and dienamides by ruthenium-catalyzed co-oligomerization of N-vinylamides with alkenes or alkynes. Angew Chem Int Ed 46:5160Google Scholar
  163. 163.
    Kondo T, Takagi D, Tsujita H, Ura Y, Wada K, Mitsudo T, Kondo T (2007) Highly selective dimerization of styrenes and linear co-dimerization of styrenes with ethylene catalyzed by a ruthenium complex. Angew Chem Int Ed 46:5958Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  1. 1.Chemical Resources Laboratory (R1-04)Tokyo Institute of TechnologyYokohamaJapan

Personalised recommendations