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The Development of Iron Catalysts for Cross-Coupling Reactions

Part of the Topics in Organometallic Chemistry book series (TOPORGAN,volume 50)

Abstract

Cross-coupling between organometallic nucleophiles and organic electrophiles is currently one of the most widely investigated areas of organic homogeneous catalysis with iron. This overview charts the development and application of iron catalysts for cross-coupling reactions, focusing predominantly on findings over the last 5 years.

Keywords

  • Cross-coupling
  • Iron
  • Iron catalysis

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  • DOI: 10.1007/3418_2015_99
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Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
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Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
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Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30

Abbreviations

acac:

Acetylacetonate

Ar:

Aryl

9-BBN:

9-Borabicyclo[3.3.1]nonane

bmim:

1-Butyl-3-methylimidazolium

cat:

Catalyst

Cp:

Cyclopentadienyl

dpbz:

1,2-Bis(diphenylphosphino)benzene

dppe:

1,2-Bis(diphenylphosphino)ethane

dppp:

1,3-Bis(diphenylphosphino)propane

EPR:

Electron paramagnetic resonance

Mes:

Mesityl, 2,4,6-trimethylphenyl

NHC:

N-heterocyclic carbene

NMP:

N-methylpyrrolidone

salen:

N,N′-ethylenebis(salicylimine)

Tf:

Triflate

THF:

Tetrahydrofuran

TMEDA:

N,N,N′,N′-tetramethyl-1,2-ethylenediamine

TMS:

Trimethylsilyl

Ts:

Tosyl

Xantphos:

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

References

  1. Vavon G, Mottez P (1944) Action des dèrivés halogénés sur les magnésiens aromatiques en prèsence de chlorure ferrique. C R Hebd Seances Acad Sci 218:557–559

    CAS  Google Scholar 

  2. Tamura M, Kochi J (1971) Vinylation of Grignard reagents – catalysis by iron. J Am Chem Soc 93:1487–1489

    CAS  CrossRef  Google Scholar 

  3. Tamura M, Kochi J (1971) Coupling of Grignard reagents with organic halides. Synthesis 3:303–305

    CrossRef  Google Scholar 

  4. Neumann SM, Kochi JK (1975) Synthesis of olefins. Cross-coupling of alkenyl halides and Grignard reagents catalyzed by iron complexes. J Org Chem 40:599–606

    CAS  CrossRef  Google Scholar 

  5. Smith RS, Kochi JK (1976) Mechanistic studies of iron catalysis in the cross coupling of alkenyl halides and Grignard reagents. J Org Chem 41:502–509

    CAS  CrossRef  Google Scholar 

  6. Kochi JK (1974) Electron-transfer mechanisms for organometallic intermediates in catalytic reactions. Acc Chem Res 7:351–360

    CAS  CrossRef  Google Scholar 

  7. Molander GA, Rahn BJ, Shubert DC, Bonde SE (1983) Iron catalyzed cross-coupling reactions. Synthesis of arylethenes. Tetrahedron Lett 24:5449–5452

    CAS  CrossRef  Google Scholar 

  8. Cahiez G, Avedissian H (1998) Highly stereo- and chemoselective iron-catalyzed alkenylation of organomagnesium compounds. Synthesis 8:1199–1205

    CrossRef  Google Scholar 

  9. Cahiez G, Marquais S (1996) Cu-catalyzed alkylation and Fe catalyzed alkenylation of organomanganese reagents. Pure Appl Chem 68:53–60

    CAS  CrossRef  Google Scholar 

  10. Dohle W, Kopp F, Cahiez G, Knochel P (2001) Fe(III)-catalyzed cross-coupling between functionalized arylmagnesium compounds and alkenyl halides. Synlett 12:1901–1904

    CrossRef  Google Scholar 

  11. Fürstner A, Leitner A (2002) Iron-catalyzed cross-coupling reactions of alkyl Grignard reagents with aryl chlorides, tosylates, and triflates. Angew Chem Int Ed 41:609–612

    CrossRef  Google Scholar 

  12. Fürstner A, Leitner A, Méndez M, Krause H (2002) Iron-catalyzed cross-coupling reactions. J Am Chem Soc 124:13856–13863

    CrossRef  Google Scholar 

  13. Fürstner A, Leitner A (2003) A catalytic approach to (R)-(+)-muscopyridine with integrated “self-clearance”. Angew Chem Int Ed 42:308–311

    CrossRef  Google Scholar 

  14. Martin R, Fürstner A (2004) Cross-coupling of alkyl halides with aryl Grignard reagents catalyzed by a low-valent iron complex. Angew Chem Int Ed 43:3955–3957

    CAS  CrossRef  Google Scholar 

  15. Nakamura M, Matsuo K, Ito S, Nakamura E (2004) Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl Grignard reagents. J Am Chem Soc 126:3686–3687

    CAS  CrossRef  Google Scholar 

  16. Nagano T, Hayashi T (2004) Iron-catalyzed grignard cross-coupling with alkyl halides possessing β-hydrogens. Org Lett 6:1297–1299

    CAS  CrossRef  Google Scholar 

  17. Bedford RB, Bruce DW, Frost RM, Goodby JW, Hird M (2004) Iron(III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens. Chem Commun:2822–2823

    Google Scholar 

  18. Bedford RB, Bruce DW, Frost RM, Hird M (2005) Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens. Chem Commun:4161–4163

    Google Scholar 

  19. Bedford RB, Betham M, Bruce DW, Danopoulos AA, Frost RM, Hird M (2006) Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary alkyl halides with aryl Grignard reagents. J Org Chem 71:1104–1110

    CAS  CrossRef  Google Scholar 

  20. Fürstner A, Martin R, Krause H, Seidel G, Goddard R, Lehmann CW (2008) Preparation, structure, and reactivity of nonstabilized organoiron compounds. Implications for iron-catalyzed cross coupling reactions. J Am Chem Soc 130:8773–8787

    CrossRef  Google Scholar 

  21. Sherry BD, Fürstner A (2008) The promise and challenge of iron-catalyzed cross coupling. Acc Chem Res 41:1500–1511

    CAS  CrossRef  Google Scholar 

  22. Jegelka M, Plietker B (2011) Catalysis by means of complex ferrates. Top Organomet Chem 33:177–213

    CAS  Google Scholar 

  23. Sun C-L, Fürstner A (2013) Formal ring-opening/cross-coupling reactions of 2-pyrones: iron-catalyzed entry into stereodefined dienyl carboxylates. Angew Chem Int Ed 52:13071–13075

    CAS  CrossRef  Google Scholar 

  24. Cahiez G, Gager O, Habiak V (2008) Iron-catalyzed alkenylation of Grignard reagents by enol phosphates. Synthesis 16:2636–2644

    CrossRef  Google Scholar 

  25. Cahiez G, Habiak V, Gager O (2008) Efficient preparation of terminal conjugated dienes by coupling of dienol phosphates with Grignard reagents under iron catalysis. Org Lett 10:2389–2392

    CAS  CrossRef  Google Scholar 

  26. Bartoccini F, Piersanti G, Armaroli S, Cerri A, Cabri W (2014) Development of a practical and sustainable strategy for the synthesis of ST1535 by an iron-catalyzed Kumada cross-coupling reaction. Tetrahedron Lett 55:1376–1378

    CAS  CrossRef  Google Scholar 

  27. Guo W-J, Wang Z-X (2013) Iron-catalyzed cross-coupling of aryltrimethylammonium triflates and alkyl Grignard reagents. Tetrahedron 69:9580–9585

    CAS  CrossRef  Google Scholar 

  28. Malhotra S, Seng PS, Koenig SG, Deese AJ, Ford KA (2013) Chemoselective sp2-sp3 cross-couplings: Iron-catalyzed alkyl transfer to dihaloaromatics. Org Lett 15:3698–3701

    CAS  CrossRef  Google Scholar 

  29. Gülak S, Jacobi von Wangelin A (2012) Chlorostyrenes in iron-catalyzed biaryl coupling reactions. Angew Chem Int Ed 51:1357–1361

    CrossRef  Google Scholar 

  30. Ding K, Zannat F, Morris JC, Brennessel WW, Holland PL (2009) Coordination of N-methylpyrrolidone to iron(II). J Organomet Chem 694:4204–4208

    CAS  CrossRef  Google Scholar 

  31. Kuzmina OM, Steib AK, Flubacher D, Knochel P (2012) Iron-catalyzed cross-coupling of N-heterocyclic chlorides and bromides with arylmagnesium reagents. Org Lett 14:4818–4821

    CAS  CrossRef  Google Scholar 

  32. Cheung CW, Ren P, Hu X (2014) Mild and phosphine-free iron-catalyzed cross-coupling of nonactivated secondary alkyl halides with alkynyl Grignard reagents. Org Lett 16:2566–2569

    CAS  CrossRef  Google Scholar 

  33. Guerinot A, Reymond S, Cossy J (2007) Iron-catalyzed cross-coupling of alkyl halides with alkenyl Grignard reagents. Angew Chem Int Ed 46:6521–6524

    CAS  CrossRef  Google Scholar 

  34. Denmark SE, Cresswell AJ (2013) Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents. J Org Chem 78:12593–12628

    CAS  CrossRef  Google Scholar 

  35. Cahiez G, Habiak V, Duplais C, Moyeux A (2007) Iron-catalyzed alkylations of aromatic Grignard reagents. Angew Chem Int Ed 46:4364–4366

    CAS  CrossRef  Google Scholar 

  36. Rushworth PJ, Hulcoop DG, Fox DJ (2013) Iron/tetramethylethylenediamine-catalyzed ambient-temperature coupling of alkyl Grignard reagents and aryl chlorides. J Org Chem 78:9517–9521

    CAS  CrossRef  Google Scholar 

  37. Czaplik WM, Mayer M, Jacobi von Wangelin A (2009) Domino iron catalysis: direct aryl-alkyl cross-coupling. Angew Chem Int Ed 48:607–610

    CAS  CrossRef  Google Scholar 

  38. Czaplik WM, Mayer M, Jacobi von Wangelin A (2011) Iron-catalyzed reductive aryl-alkenyl cross-coupling reactions. ChemCatChem 3:135–138

    CAS  CrossRef  Google Scholar 

  39. Greenhalgh MD, Kolodziej A, Sinclair F, Thomas SP (2014) Iron-catalyzed hydromagnesiation: synthesis and characterization of benzylic Grignard reagent intermediate and application in the synthesis of ibuprofen. Organometallics 33:5811–5819

    CAS  CrossRef  Google Scholar 

  40. Greenhalgh MD, Thomas SP (2012) Iron-catalyzed, highly regioselective synthesis of α-aryl carboxylic acids from styrene derivatives and CO2. J Am Chem Soc 134:11900–11903

    CAS  CrossRef  Google Scholar 

  41. Noda D, Sunada Y, Hatakeyama T, Nakamura M, Nagashima H (2009) Effect of TMEDA on iron-catalyzed coupling reactions of ArMgX with alkyl halides. J Am Chem Soc 131:6078–6079

    CAS  CrossRef  Google Scholar 

  42. Bedford RB, Brenner PB, Carter E, Cogswell PM, Haddow MF, Harvey JN, Murphy DM, Nunn J, Woodall CH (2014) TMEDA in iron-catalyzed Kumada coupling: amine adduct versus homoleptic “ate” complex formation. Angew Chem Int Ed 53:1804–1808

    CAS  CrossRef  Google Scholar 

  43. Bedford RB, Betham M, Bruce DW, Davis SA, Frost RM, Hird M (2006) Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents. Chem Commun:1398–1400

    Google Scholar 

  44. Kuzmina OM, Steib AK, Markiewicz JT, Flubacher D, Knochel P (2013) Ligand-accelerated iron- and cobalt-catalyzed cross-coupling reactions between N-heteroaryl halides and aryl magnesium reagents. Angew Chem Int Ed 52:4945–4949

    CAS  CrossRef  Google Scholar 

  45. Chowdhury RR, Crane AK, Fowler C, Kwong P, Kozak CM (2008) Iron(III) amine-bis(phenolate) complexes as catalysts for the coupling of alkyl halides with aryl Grignard reagents. Chem Commun:94–96

    Google Scholar 

  46. Hasan K, Dawe LN, Kozak CM (2011) Synthesis, structure, and C-C cross-coupling activity of (amine)bis(phenolato)iron(acac) complexes. Eur J Inorg Chem 29:4610–4621

    CrossRef  Google Scholar 

  47. Reckling AM, Martin D, Dawe LN, Decken A, Kozak CM (2011) Structure and C-C cross-coupling reactivity of iron(III) complexes of halogenated amine-bis(phenolate) ligands. J Organomet Chem 696:787–794

    CAS  CrossRef  Google Scholar 

  48. Qian X, Dawe LN, Kozak CM (2011) Catalytic alkylation of aryl Grignard reagents by iron(III) amine-bis(phenolate) complexes. Dalton Trans 40:933–943

    CAS  CrossRef  Google Scholar 

  49. Chard EF, Dawe LN, Kozak CM (2013) Coupling of benzyl halides with aryl Grignard reagents catalyzed by iron(III) amine-bis(phenolate) complexes. J Organomet Chem 737:32–39

    CAS  CrossRef  Google Scholar 

  50. Cahiez G, Gager O, Buendia J, Patinote C (2012) Iron thiolate complexes: efficient catalysts for coupling alkenyl halides with alkyl Grignard reagents. Chem Eur J 18:5860–5863

    CAS  CrossRef  Google Scholar 

  51. Dongol KG, Koh H, Sau M, Chai CLL (2007) Iron-catalysed sp3–sp3 cross-coupling reactions of unactivated alkyl halides with alkyl Grignard reagents. Adv Synth Catal 349:1015–1018

    CAS  CrossRef  Google Scholar 

  52. Hatakeyama T, Fujiwara Y, Okada Y, Itoh T, Hashimoto T, Kawamura S, Ogata K, Takaya H, Nakamura M (2011) Kumada-Tamao-Corriu coupling of alkyl halides catalyzed by an iron-bisphosphine complex. Chem Lett 40:1030–1032

    CAS  CrossRef  Google Scholar 

  53. Kawamura S, Nakamura M (2013) Ligand-controlled iron-catalyzed cross coupling of benzylic chlorides with aryl Grignard reagents. Chem Lett 42:183–185

    CAS  CrossRef  Google Scholar 

  54. Hatakeyama T, Okada Y, Yoshimoto Y, Nakamura M (2011) Tuning chemoselectivity in iron-catalyzed Sonogashira-type reactions using a bisphosphine ligand with peripheral steric bulk: selective alkynylation of nonactivated alkyl halides. Angew Chem Int Ed 50:10973–10976

    CAS  CrossRef  Google Scholar 

  55. Sun C-L, Krause H, Fürstner A (2014) A practical procedure for iron-catalyzed cross-coupling reactions of sterically hindered aryl-Grignard reagents with primary alkyl halides. Adv Synth Catal 356:1281–1291

    CAS  CrossRef  Google Scholar 

  56. Bica K, Gaertner P (2006) An iron-containing ionic liquid as recyclable catalyst for aryl Grignard cross-coupling of alkyl halides. Org Lett 8:733–735

    CAS  CrossRef  Google Scholar 

  57. Ghorai SK, Jin M, Hatakeyama T, Nakamura M (2012) Cross-coupling of non-activated chloroalkanes with aryl Grignard reagents in the presence of iron/N-heterocyclic carbene catalysts. Org Lett 14:1066–1069

    CAS  CrossRef  Google Scholar 

  58. Silberstein AL, Ramgren SD, Garg NK (2012) Iron-catalyzed alkylations of aryl sulfamates and carbamates. Org Lett 14:3796–3799

    CAS  CrossRef  Google Scholar 

  59. Perry MC, Gillett AN, Law TC (2012) An unprecedented iron-catalyzed cross-coupling of primary and secondary alkyl Grignard reagents with non-activated aryl chlorides. Tetrahedron Lett 53:4436–4439

    CAS  CrossRef  Google Scholar 

  60. Agrawal T, Cook SP (2013) Iron-catalyzed cross-coupling reactions of alkyl Grignards with aryl sulfamates and tosylates. Org Lett 15:96–99

    CAS  CrossRef  Google Scholar 

  61. Guisan-Ceinos M, Tato F, Bunuel E, Calle P, Cardenas DJ (2013) Fe-catalyzed Kumada-type alkyl-alkyl cross-coupling. Evidence for the intermediacy of Fe(I) complexes. Chem Sci 4:1098–1104

    CAS  CrossRef  Google Scholar 

  62. Hatakeyama T, Nakamura M (2007) Iron-catalyzed selective biaryl coupling: remarkable suppression of homocoupling by the fluoride anion. J Am Chem Soc 129:9844–9845

    CAS  CrossRef  Google Scholar 

  63. Hatakeyama T, Hashimoto S, Ishizuka K, Nakamura M (2009) Highly selective biaryl cross-coupling reactions between aryl halides and aryl Grignard reagents: a new catalyst combination of N-heterocyclic carbenes and iron, cobalt, and nickel fluorides. J Am Chem Soc 131:11949–11963

    CAS  CrossRef  Google Scholar 

  64. Chua Y-Y, Duong HA (2014) Selective Kumada biaryl cross-coupling reaction enabled by an iron(III) alkoxide-N-heterocyclic carbene catalyst system. Chem Commun 50:8424–8427

    CAS  CrossRef  Google Scholar 

  65. Sapountzis I, Lin W, Kofink CC, Despotopoulou C, Knochel P (2005) Iron-catalyzed aryl–aryl cross-couplings with magnesium-derived copper reagents. Angew Chem Int Ed 44:1654–1657

    CAS  CrossRef  Google Scholar 

  66. Dunet G, Knochel P (2006) Iron-catalyzed cross-coupling between alkenyl and dienyl sulfonates and functionalized arylcopper reagents. Synlett 3:407–410

    Google Scholar 

  67. Kofink CC, Blank B, Pagano S, Götz N, Knochel P (2007) Iron-catalyzed aryl–aryl cross-coupling reaction tolerating amides and unprotected quinolinones. Chem Commun:1954–1956

    Google Scholar 

  68. Castagnolo D, Botta M (2010) Iron-catalyzed cross-coupling between 1-bromoalkynes and Grignard-derived organocuprate reagents. Eur J Org Chem 2010(24):3224–3228

    CrossRef  Google Scholar 

  69. Cahiez G, Marquais S (1996) Highly chemo- and stereoselective Fe-catalyzed alkenylation of organomanganese reagents. Tetrahedron Lett 37:1773–1776

    CAS  CrossRef  Google Scholar 

  70. Hatakeyama T, Nakagawa N, Nakamura M (2009) Iron-catalyzed Negishi coupling toward an effective olefin synthesis. Org Lett 11:4496–4499

    CAS  CrossRef  Google Scholar 

  71. Ito S, Fujiwara Y, Nakamura E, Nakamura M (2009) Iron-catalyzed cross-coupling of alkyl sulfonates with arylzinc reagents. Org Lett 11:4306–4309

    CAS  CrossRef  Google Scholar 

  72. Bedford RB, Huwe M, Wilkinson MC (2009) Iron-catalysed Negishi coupling of benzyl halides and phosphates. Chem Commun:600–602

    Google Scholar 

  73. Bedford RB, Hall MA, Hodges GR, Huwe M, Wilkinson MC (2009) Simple mixed Fe-Zn catalysts for the Suzuki couplings of tetraarylborates with benzyl halides and 2-halopyridines. Chem Commun:6430–6432

    Google Scholar 

  74. Hatakeyama T, Kondo Y, Fujiwara YI, Takaya H, Ito S, Nakamura E, Nakamura M (2009) Iron-catalysed fluoroaromatic coupling reactions under catalytic modulation with 1,2-bis(diphenylphosphino)benzene. Chem Commun:1216–1218

    Google Scholar 

  75. Adams CJ, Bedford RB, Carter E, Gower NJ, Haddow MF, Harvey JN, Huwe M, Cartes MA, Mansell SM, Mendoza C, Murphy DM, Neeve EC, Nunn J (2012) Iron(I) in Negishi cross-coupling reactions. J Am Chem Soc 134:10333–10336

    CAS  CrossRef  Google Scholar 

  76. Bedford RB, Carter E, Cogswell PM, Gower NJ, Haddow MF, Harvey JN, Murphy DM, Neeve EC, Nunn J (2013) Simplifying iron-phosphine catalysts for cross-coupling reactions. Angew Chem Int Ed 52:1285–1288

    CAS  CrossRef  Google Scholar 

  77. Lin X, Zheng F, Qing F-L (2012) Iron-catalyzed cross-coupling reactions between arylzinc reagents and alkyl halides bearing β-fluorines. Organometallics 31:1578–1582

    CAS  CrossRef  Google Scholar 

  78. Guo Y, Young DJ, Hor TSA (2008) Palladium-free Suzuki-Miyaura cross-coupling at elevated pressures. Tetrahedron Lett 49:5620–5621

    CAS  CrossRef  Google Scholar 

  79. Bedford RB, Nakamura M, Gower NJ, Haddow MF, Hall MA, Huwe M, Hashimoto T, Okopie RA (2009) Iron-catalysed Suzuki coupling? A cautionary tale. Tetrahedron Lett 50:6110–6111

    CAS  CrossRef  Google Scholar 

  80. Kylmälä T, Valkonen A, Rissanen K, Xu Y, Franzén R (2009) Retraction notice to “trans-Tetrakis(pyridine)dichloroiron(II) as catalyst for Suzuki cross-coupling in ethanol and water”. doi:10.1016/j.tetlet.2009.07.103

  81. Bézier D, Darcel C (2010) Retraction: iron-catalyzed Suzuki–Miyaura cross-coupling reaction. Adv Synth Catal 2010(352):1081

    CrossRef  Google Scholar 

  82. Yu Y, Brennessel WW, Holland PL (2007) Borane B-C bond cleavage by a low-coordinate iron hydride complex and N-N Bond cleavage by the hydridoborate product. Organometallics 26:3217–3226

    CAS  CrossRef  Google Scholar 

  83. Dunsford JJ, Cade IA, Fillman KL, Neidig ML, Ingleson MJ (2014) Reactivity of (NHC)2FeX2 complexes toward arylborane Lewis acids and arylboronates. Organometallics 33:370–377

    CAS  CrossRef  Google Scholar 

  84. Bedford RB, Brenner PB, Carter E, Clifton J, Cogswell PM, Gower NJ, Haddow MF, Harvey JN, Kehl JA, Murphy DM, Neeve EC, Neidig ML, Nunn J, Snyder BER, Taylor J (2014) Iron phosphine catalyzed cross-coupling of tetraorganoborates and related Group 13 nucleophiles with alkyl halides. Organometallics 33:5767–5780

    CAS  CrossRef  Google Scholar 

  85. Hatakeyama T, Hashimoto T, Kathriarachchi K, Zenmyo T, Seike H, Nakamura M (2012) Iron-catalyzed alkyl-alkyl Suzuki-Miyaura coupling. Angew Chem Int Ed 51:8834–8837

    CAS  CrossRef  Google Scholar 

  86. Hatakeyama T, Hashimoto T, Kondo Y, Fujiwara Y, Seike H, Takaya H, Tamada Y, Ono T, Nakamura M (2010) Iron-catalyzed Suzuki-Miyaura coupling of alkyl halides. J Am Chem Soc 132:10674–10676

    CAS  CrossRef  Google Scholar 

  87. Hashimoto T, Hatakeyama T, Nakamura M (2012) Stereospecific cross-coupling between alkenylboronates and alkyl halides catalyzed by iron–bisphosphine complexes. J Org Chem 77:1168–1173

    CAS  CrossRef  Google Scholar 

  88. Bedford RB, Brenner PB, Carter E, Carvell TW, Cogswell PM, Gallagher T, Harvey JN, Murphy DM, Neeve EC, Nunn J, Pye DR (2014) Expedient iron-catalyzed coupling of alkyl, benzyl and allyl halides with arylboronic esters. Chem Eur J 20:7935–7938

    CAS  CrossRef  Google Scholar 

  89. Bedford RB, Gallagher T, Pye DR, Savage W (2015) Towards iron-catalysed Suzuki Biaryl cross-coupling: unusual reactivity of 2-halobenzyl halides. doi:10.1055/s-0034-1380135

  90. Kawamura S, Ishizuka K, Takaya H, Nakamura M (2010) The first iron-catalysed aluminium-variant Negishi coupling: critical effect of co-existing salts on the dynamic equilibrium of arylaluminium species and their reactivity. Chem Commun 46:6054–6056

    CAS  CrossRef  Google Scholar 

  91. Kawamura S, Kawabata T, Ishizuka K, Nakamura M (2012) Iron-catalysed cross-coupling of halohydrins with aryl aluminium reagents: a protecting-group-free strategy attaining remarkable rate enhancement and diastereoinduction. Chem Commun 48:9376–9378

    CAS  CrossRef  Google Scholar 

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Bedford, R.B., Brenner, P.B. (2015). The Development of Iron Catalysts for Cross-Coupling Reactions. In: Bauer, E. (eds) Iron Catalysis II. Topics in Organometallic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/3418_2015_99

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