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Iron Catalysis II pp 173–216Cite as

Iron-Catalyzed Reduction and Hydroelementation Reactions

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

Abstract

During the last two decades, iron has proved to be an interesting transition metal which is a highly valuable alternative to classical precious ones for catalyzing organic transformations including the reduction of unsaturated C–C or C–heteroatom bonds. This chapter summarizes the rapid development of iron catalyzed selective reductions of alkene, alkyne, carbonyl and carboxylic derivatives. The emerging topic of hydroboration of alkenes and alkynes is also described.

Keywords

  • Alkenes
  • Alkynes
  • Carbonyl derivatives
  • Carboxylic acid derivatives
  • Hydroboration
  • Hydrogen transfer
  • Hydrogenation
  • Hydrosilylation
  • Iron
  • Reduction

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  • DOI: 10.1007/3418_2015_104
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Scheme 1
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Fig. 1
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Fig. 2
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Fig. 5
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Fig. 7
Fig. 8
Scheme 29
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Scheme 38
Scheme 39
Scheme 40
Scheme 41
Scheme 42
Scheme 43
Scheme 44
Scheme 45
Scheme 46
Scheme 47
Scheme 48
Scheme 49
Scheme 50
Scheme 51

Abbreviations

cat:

Catechol

cod:

1,5-Cyclooctadiene

Cp:

Cyclopentadienyl

dcpe:

1,2-Bisdicyclohexylphosphinoethane

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DFT:

Density functional theory

Dipp:

2,6-Diisopropylphenyl

DMC:

Dimethyl carbonate

DRA:

Direct reductive amination

EDTA-Na2 :

Ethylenediaminetetraacetic acid disodium salt

IMes:

1,3-Bis(2,4,6-trimethylphenyl) imidazole-2-ylidene

IPr:

1,3-Bis(2,6-diisopropylphenyl) imidazole-2-ylidene

MD’M:

[(MeO)2MeSiH]

Mes:

2,4,6-Trimethylphenyl

NHC:

N-Heterocyclic carbene

NPs:

Nanoparticles

pin:

Pinacol

PMHS:

Polymethylhydrosiloxane

t-PBO:

trans-4-Phenyl-but-3-en-2-one

terpy:

2,2′:6′,2″-Terpyridine

TFA:

Trifluoroacetic acid

TMDS:

1,1,3,3-Tetramethyldisiloxane

TMEDA:

N,N,N′,N′-Tetramethylethylenediamine

TMPP:

Tris(2,4,6-trimethoxyphenyl)phosphine

TOF:

Turnover frequency

TON:

Turnover number

References

  1. Bolm C, Legros J, Le Paih J, Zani L (2004) Chem Rev 104:6217

    CAS  Google Scholar 

  2. Plietker B (2008) Iron catalysis in organic chemistry. Wiley-VCH Verlag, Weinheim

    Google Scholar 

  3. Bauer EB (2008) Curr Org Chem 12:1341

    CAS  Google Scholar 

  4. Sun CL, Li BJ, Shi ZJ (2011) Chem Rev 111:1293

    CAS  Google Scholar 

  5. Bézier D, Sortais JB, Darcel C (2013) Adv Synth Catal 355:19

    Google Scholar 

  6. Gopalaiah K (2013) Chem Rev 113:3248

    CAS  Google Scholar 

  7. Riener K, Haslinger S, Raba A, Högerl MP, Cokoja M, Herrmann WA, Kühn FE (2014) Chem Rev 114:5215

    CAS  Google Scholar 

  8. Junge K, Schröder K, Beller M (2011) Chem Commun 47:4849

    CAS  Google Scholar 

  9. Le Bailly BAF, Thomas SP (2011) RSC Adv 1435

    Google Scholar 

  10. Zhang M, Zhang A (2010) Appl Organomet Chem 24:751

    CAS  Google Scholar 

  11. Morris RH (2009) Chem Soc Rev 38:2282

    CAS  Google Scholar 

  12. Gaillard S, Renaud JL (2008) ChemSusChem 1:505

    CAS  Google Scholar 

  13. Frankel EN, Emken EA, Peters HM, Davison VL, Butterfield RO (1964) J Org Chem 29:3292

    CAS  Google Scholar 

  14. Frankel EN, Emken EA, Davison VL (1965) J Org Chem 30:2739

    CAS  Google Scholar 

  15. Schroeder MA, Wrighton MS (1976) J Am Chem Soc 98:551

    CAS  Google Scholar 

  16. Inoue H, Suzuki M (1980) J Chem Soc Chem Commun 817

    Google Scholar 

  17. Inoue H, Sato M (1983) J Chem Soc Chem Commun 983

    Google Scholar 

  18. Lynch TJ, Banah M, Kaesz HD, Porter CR (1984) J Org Chem 49:1266

    CAS  Google Scholar 

  19. Nishiguchi T, Fukuzumi K (1971) J Chem Soc D Chem Commun 139

    Google Scholar 

  20. Nishiguchi T, Fukuzumi K (1972) Bull Chem Soc Jap 45:1656

    CAS  Google Scholar 

  21. Bianchini C, Meli A, Peruzzini M, Vizza F, Zanobini F, Frediani P (1989) Organometallics 8:2080

    CAS  Google Scholar 

  22. Bianchini C, Meli A, Peruzzini M, Frediani P, Bohanna C, Esteruelas MA, Oro LA (1992) Organometallics 11:138

    CAS  Google Scholar 

  23. Bianchini C, Farnetti E, Graziano M, Peruzzini M, Polo A (1993) Organometallics 12:3753

    CAS  Google Scholar 

  24. Wienhöfer G, Westerhaus FA, Jagadeesh RV, Junge K, Junge H, Beller M (2012) Chem Commun 48:4827

    Google Scholar 

  25. Daida EJ, Peters JC (2004) Inorg Chem 43:7474

    CAS  Google Scholar 

  26. Fong H, Moret ME, Lee Y, Peters JC (2013) Organometallics 32:3053

    CAS  Google Scholar 

  27. Bart SC, Hawrelak EJ, Lobkovsky E, Chirik PJ (2005) Organometallics 24:5518

    CAS  Google Scholar 

  28. Bart SC, Lobkovsky E, Chirik PJ (2004) J Am Chem Soc 126:13794

    CAS  Google Scholar 

  29. Trovitch RJ, Lobkovsky E, Bill E, Chirik PJ (2008) Organometallics 27:1470

    CAS  Google Scholar 

  30. Yu RP, Darmon JM, Hoyt JM, Margulieux GW, Turner ZR, Chirik PJ (2012) ACS Catal 2:1760

    CAS  Google Scholar 

  31. Trovitch RJ, Lobkovsky E, Chirik PJ (2006) Inorg Chem 45:7252

    CAS  Google Scholar 

  32. Srimani D, Diskin-Posner Y, Ben-David Y, Milstein D (2013) Angew Chem Int Ed 52:14131

    CAS  Google Scholar 

  33. Hoyt JM, Shevlin M, Margulieux GW, Krska SW, Tudge MT, Chirik PJ (2014) Organometallics 33:5781

    CAS  Google Scholar 

  34. Phua P, Le Fort L, Boogers JAF, Tristany M, de Vries JG (2009) Chem Commun 3747

    Google Scholar 

  35. Rangheard C, de Julian FC, Phua PH, Hoorn J, Lefort L, de Vries JG (2010) Dalton Trans 39:8464

    CAS  Google Scholar 

  36. Bedford R, Betham M, Bruce D, Davis S, Frost R, Hird M (2006) Chem Commun 1398

    Google Scholar 

  37. Stein M, Wieland J, Steurer P, Toelle F, Muelhaupt R, Breit B (2011) Adv Synth Catal 353:523

    CAS  Google Scholar 

  38. Hudson R, Hamasaka G, Osako T, Yamada YMA, Li CJ, Uozumi Y, Moores A (2013) Green Chem 15:2141

    CAS  Google Scholar 

  39. Kelsen V, Wendt B, Werkmeister S, Junge K, Beller M, Chaudret B (2013) Chem Commun 49:3416

    CAS  Google Scholar 

  40. Ojima I, Li Z, Zhu J (1998) In: Rappoport Z, Apeloig Y (eds) The chemistry of organosilicon compounds, vol 2. Wiley, New York, p 1687

    Google Scholar 

  41. Speier JL (1979) Adv Organomet Chem 17:407

    CAS  Google Scholar 

  42. Karstedt BD (1973) US Patent 3 715 334

    Google Scholar 

  43. Hitchcock PB, Lappert MF, Warhurst NJW (1991) Angew Chem Int Ed Engl 30:438

    Google Scholar 

  44. Nesmeyanov AN, Freidlina RK, Chukovskaya EC, Petrova RG, Belyavsky AB (1962) Tetrahedron 17:61

    CAS  Google Scholar 

  45. Schroeder MA, Wrighton MS (1977) J Organomet Chem 128:345

    CAS  Google Scholar 

  46. Kakiuchi F, Tanaka Y, Chatani N, Murai S (1993) J Organomet Chem 456:45

    CAS  Google Scholar 

  47. Archer AM, Bouwkamp MW, Cortez MP, Lobkovsky E, Chirik PJ (2006) Organometallics 25:4269

    CAS  Google Scholar 

  48. Greenhalgh MD, Frank DJ, Thomas SP (2014) Adv Synth Catal 356:584

    CAS  Google Scholar 

  49. Tondreau AM, Hojilla Atienza CC, Weller KJ, Nye SA, Lewis KM, Delis JGP, Chirik PJ (2012) Science 335:567

    CAS  Google Scholar 

  50. Hojilla Atienza CC, Tondreau AM, Weller KJ, Lewis KM, Cruse RW, Nye SA, Boyer JL, Delis JGP, Chirik PJ (2012) ACS Catal 2:2169

    CAS  Google Scholar 

  51. Peng D, Zhang Y, Du X, Zhang L, Leng X, Walter MD, Huang Z (2013) J Am Chem Soc 135:19154

    CAS  Google Scholar 

  52. Kamata K, Suzuki A, Nakai Y, Nakazawa H (2012) Organometallics 31:3825

    CAS  Google Scholar 

  53. Tondreau AM, Hojilla Atienza CC, Darmon JM, Milsmann C, Hoyt HM, Weller KJ, Nye SA, Lewis KM, Boyer J, Delis JGP, Lobkovsky E, Chirik PJ (2012) Organometallics 31:4886

    CAS  Google Scholar 

  54. Wu JY, Stanzl BN, Ritter T (2010) J Am Chem Soc 132:13214

    CAS  Google Scholar 

  55. Enthaler S, Haberberger M, Irran E (2011) Chem Asian J 6:1613

    CAS  Google Scholar 

  56. Haberberger M, Irran E, Enthaler S (2011) Eur J Inorg Chem 2797

    Google Scholar 

  57. Belger C, Plietker B (2012) Chem Commun 48:5419

    CAS  Google Scholar 

  58. Markó L, Radhi MA, Ötvös I (1981) J Organomet Chem 218:369

    Google Scholar 

  59. Markó L, Palágyi J (1983) Trans Met Chem 8:207

    Google Scholar 

  60. Casey CP, Guan H (2007) J Am Chem Soc 129:5816

    CAS  Google Scholar 

  61. Knölker HJ, Baum E, Goesmann H, Klauss R (1999) Angew Chem Int Ed 38:2064

    Google Scholar 

  62. Fleischer S, Zhou S, Junge K, Beller M (2013) Angew Chem Int Ed 52:5120

    CAS  Google Scholar 

  63. Tlili A, Schranck J, Neumann H, Beller M (2012) Chem Eur J 18:15935

    CAS  Google Scholar 

  64. Mérel DS, Elie M, Lohier JF, Gaillard S, Renaud JL (2013) ChemCatChem 5:2939

    Google Scholar 

  65. Berkessel A, Reichau S, von der Höh A, Leconte N, Neudörfl JM (2011) Organometallics 30:3880

    CAS  Google Scholar 

  66. Casey CP, Guan H (2009) J Am Chem Soc 131:2499

    CAS  Google Scholar 

  67. Bullock RM (2007) Angew Chem Int Ed 46:7360

    CAS  Google Scholar 

  68. Zhang H, Chen D, Zhang Y, Zhang G, Liu J (2010) Dalton Trans 39:1972

    CAS  Google Scholar 

  69. Rautenstrauch V, Hoang-Cong X, Churlaud R, Abdur-Rashid K, Morris RH (2003) Chem Eur J 9:4954

    CAS  Google Scholar 

  70. Sui-Seng C, Freutel F, Lough AJ, Morris RH (2008) Angew Chem Int Ed 47:940

    CAS  Google Scholar 

  71. Sui-Seng C, Haque FN, Hadzovic A, Pütz AM, Reuss V, Meyer N, Lough AJ, Zimmer-De Iuliis M, Morris RH (2009) Inorg Chem 48:735

    CAS  Google Scholar 

  72. Zhang J, Leitus G, Ben-David Y, Milstein D (2005) J Am Chem Soc 127:10840

    CAS  Google Scholar 

  73. Zhang J, Leitus G, Ben-David Y, Milstein D (2006) Angew Chem Int Ed 45:1113

    CAS  Google Scholar 

  74. Balaraman E, Gnanaprakasam B, Shimon LJW, Milstein D (2010) J Am Chem Soc 132:16756

    CAS  Google Scholar 

  75. Gunanathan C, Milstein D (2011) Acc Chem Res 44:588

    CAS  Google Scholar 

  76. Langer R, Leitus G, Ben-David Y, Milstein D (2011) Angew Chem Int Ed 50:2120

    CAS  Google Scholar 

  77. Yang X (2011) Inorg Chem 50:12836

    CAS  Google Scholar 

  78. Langer R, Iron MA, Konstantinovski L, Diskin-Posner Y, Leitus G, Ben-David Y, Milstein D (2012) Chem Eur J 18:7196

    CAS  Google Scholar 

  79. Lagaditis PO, Sues PE, Sonnenberg JF, Wan KY, Lough AJ, Morris RH (2014) J Am Chem Soc 136:1367

    CAS  Google Scholar 

  80. Wienhöfer G, Westerhaus FA, Junge K, Ludwig R, Beller M (2013) Chem Eur J 19:7701

    Google Scholar 

  81. Li Y, Yu S, Wu X, Xiao J, Shen W, Dong Z, Gao J (2014) J Am Chem Soc 136:4031

    CAS  Google Scholar 

  82. Lu LQ, Li Y, Junge K, Beller M (2013) Angew Chem Int Ed 52:8382

    CAS  Google Scholar 

  83. Jothimony K, Vancheesen S (1989) J Mol Catal 52:301

    CAS  Google Scholar 

  84. Jothimony K, Vancheesen S, Kuriacose JC (1985) J Mol Catal 32:11

    CAS  Google Scholar 

  85. Enthaler S, Hagemann B, Erre G, Junge K, Beller M (2006) Chem Asian J 1:598

    CAS  Google Scholar 

  86. Enthaler S, Erre G, Tse MK, Junge K, Beller M (2006) Tetrahedron Lett 47:8095

    CAS  Google Scholar 

  87. Enthaler S, Spilker B, Erre G, Junge K, Tse MK, Beller M (2008) Tetrahedron 64:3867

    CAS  Google Scholar 

  88. Polshettiwar V, Varma RS (2009) Green Chem 11:1313

    CAS  Google Scholar 

  89. Chen JS, Chen LL, Xing Y, Chen G, Shen WY, Dong ZR, Li YY, Gao JX (2004) Huaxue Xuebao 62:1745

    CAS  Google Scholar 

  90. Meyer N, Lough AJ, Morris RH (2009) Chem Eur J 15:5605

    CAS  Google Scholar 

  91. Mikhailine AA, Lough AJ, Morris RH (2009) J Am Chem Soc 131:1394

    CAS  Google Scholar 

  92. Lagaditis PO, Lough AJ, Morris RH (2010) Inorg Chem 49:10057

    CAS  Google Scholar 

  93. Mikhailine AA, Morris RH (2010) Inorg Chem 49:11039

    CAS  Google Scholar 

  94. Sues PE, Lough AJ, Morris RH (2011) Organometallics 30:4418

    CAS  Google Scholar 

  95. Mikhailine AA, Kim E, Dingels C, Lough AJ, Morris RH (2008) Inorg Chem 47:6587

    CAS  Google Scholar 

  96. Lagaditis PO, Lough AJ, Morris RH (2011) J Am Chem Soc 133:9662

    CAS  Google Scholar 

  97. Zuo W, Lough AJ, Feng Y, Morris RH (2013) Science 342:1080

    CAS  Google Scholar 

  98. Buchard A, Heuclin H, Auffrant A, Le Goff XF, Le Floch P (2009) Dalton Trans 1659

    Google Scholar 

  99. Yu S, Shen W, Li Y, Dong Z, Xu Y, Li Q, Zhang J, Gao J (2012) Adv Synth Catal 354:818

    CAS  Google Scholar 

  100. Kandepi VVKM, Cardoso JMS, Peris E, Royo B (2010) Organometallics 29:2777

    CAS  Google Scholar 

  101. Bala MD, Ikhile MI (2014) J Mol Catal A Chem 385:98

    CAS  Google Scholar 

  102. Wienhöfer G, Westerhaus FA, Junge K, Beller M (2013) J Organomet Chem 744:156

    Google Scholar 

  103. Brunner H, Fisch K (1990) Angew Chem Int Ed Engl 29:1131

    Google Scholar 

  104. Shaikh NS, Junge K, Beller M (2007) Org Lett 9:5429

    CAS  Google Scholar 

  105. Addis D, Shaikh NS, Zhou S, Das S, Junge K, Beller M (2010) Chem Asian J 5:1687

    CAS  Google Scholar 

  106. Shaikh NS, Enthaler S, Junge K, Beller M (2008) Angew Chem Int Ed 47:2497

    CAS  Google Scholar 

  107. Nishiyama H, Furuta A (2007) Chem Commun 760

    Google Scholar 

  108. Furuta A, Nishiyama H (2008) Tetrahedron Lett 49:110

    CAS  Google Scholar 

  109. Inagaki T, Phong LT, Furuta A, Ito JI, Nishiyama H (2010) Chem Eur J 16:3090

    CAS  Google Scholar 

  110. Langlotz BK, Wadepohl H, Gade LH (2008) Angew Chem Int Ed 47:4670

    CAS  Google Scholar 

  111. Tondreau AM, Darmon JM, Wile BM, Floyd SK, Lobkovsky E, Chirik PJ (2009) Organometallics 28:3928

    CAS  Google Scholar 

  112. Muller K, Schubert A, Jozak T, Ahrens-Botzong A, Schünemann V, Thiel WR (2011) ChemCatChem 3:887

    CAS  Google Scholar 

  113. Plietker B, Dieskau A (2009) Eur J Org Chem 775

    Google Scholar 

  114. Holzwarth M, Dieskau A, Tabassam M, Plietker B (2009) Angew Chem Int Ed 48:7251

    CAS  Google Scholar 

  115. Dieskau A, Begouin JM, Plietker B (2011) Eur J Org Chem 5291

    Google Scholar 

  116. Yang J, Tilley TD (2010) Angew Chem Int Ed 49:10186

    CAS  Google Scholar 

  117. Tondreau AA, Lobkovsky E, Chirik PJ (2008) Org Lett 10:2789

    CAS  Google Scholar 

  118. Bhattacharya P, Krause JA, Guan H (2011) Organometallics 30:4720

    CAS  Google Scholar 

  119. Wu S, Li X, Xiong Z, Xu W, Lu Y, Sun H (2013) Organometallics 32:3227

    CAS  Google Scholar 

  120. Zuo Z, Sun H, Wang L, Li X (2014) Dalton Trans 43:1176

    Google Scholar 

  121. Gutsulyak DV, Kuzmina LG, Howard JAK, Vyboishchikov SF, Nikonov GI (2008) J Am Chem Soc 130:3732

    CAS  Google Scholar 

  122. Zheng J, Misal Castro LC, Roisnel T, Darcel C, Sortais JB (2012) Inorg Chim Acta 380:301

    CAS  Google Scholar 

  123. Jiang F, Bézier D, Sortais JB, Darcel C (2011) Adv Synth Catal 353:239

    CAS  Google Scholar 

  124. Bézier D, Jiang F, Roisnel T, Sortais JB, Darcel C (2012) Eur J Inorg Chem 1333

    Google Scholar 

  125. Demir S, Gökçe Y, Kaloğlu N, Sortais JB, Darcel C, Özdemir İ (2013) Appl Organomet Chem 27:459

    CAS  Google Scholar 

  126. César V, Misal Castro LC, Dombray T, Sortais JB, Darcel C, Labat S, Miqueu K, Sotiropoulos JM, Brousses R, Lugan N, Lavigne G (2013) Organometallics 32:4643

    Google Scholar 

  127. Kumar D, Prakasham AP, Bheeter LP, Sortais JB, Gangwar M, Roisnel T, Kalita A, Darcel C, Ghosh P (2014) J Organomet Chem 762:81

    CAS  Google Scholar 

  128. Buitrago E, Zani L, Adolfsson H (2011) Appl Organomet Chem 25:748

    CAS  Google Scholar 

  129. Buitrago E, Tinnis F, Adolfsson H (2012) Adv Synth Catal 354:217

    CAS  Google Scholar 

  130. Hashimoto T, Urban S, Hoshino R, Ohki Y, Tatsumi K, Glorius F (2012) Organometallics 31:4474

    CAS  Google Scholar 

  131. Grohmann C, Hashimoto T, Fröhlich R, Ohki Y, Tatsumi K, Glorius F (2012) Organometallics 31:8047

    CAS  Google Scholar 

  132. Warratz S, Postigo L, Royo B (2013) Organometallics 32:893

    CAS  Google Scholar 

  133. Dal Zotto RC, Virieux D, Campagne JM (2009) Synlett 276

    Google Scholar 

  134. Zhou S, Fleischer S, Junge K, Beller M (2011) Angew Chem Int Ed 50:5120

    CAS  Google Scholar 

  135. Fleischer S, Werkmeister S, Zhou S, Junge K, Beller M (2012) Chem Eur J 18:9005

    CAS  Google Scholar 

  136. Fleischer S, Zhou S, Werkmeister S, Junge K, Beller M (2013) Chem Eur J 19:4997

    CAS  Google Scholar 

  137. Chakraborty S, Brennessel WW, Jones WD (2014) J Am Chem Soc 136:8564

    CAS  Google Scholar 

  138. Zhou S, Fleischer S, Junge K, Das S, Addis D, Beller M (2010) Angew Chem Int Ed 49:8121

    CAS  Google Scholar 

  139. Mikhailine AA, Maishan MI, Morris RH (2012) Org Lett 14:4638

    CAS  Google Scholar 

  140. Misal Castro LC, Sortais JB, Darcel C (2012) Chem Commun 48:151

    Google Scholar 

  141. Knifton JF (1976) J Org Chem 41:1200

    CAS  Google Scholar 

  142. Deshpande RM, Mahajan AN, Diwakar MM, Ozarde PS, Chaudhari RV (2004) J Org Chem 69:4835

    CAS  Google Scholar 

  143. Wienhöfer G, Baseda-Krüger M, Ziebart C, Westerhaus FA, Baumann W, Jackstell R, Junge K, Beller M (2013) Chem Commun 49:9089

    Google Scholar 

  144. Wienhöfer G, Sorribes I, Boddien A, Westerhaus F, Junge K, Junge H, Llusar R, Beller M (2012) J Am Chem Soc 133:12875

    Google Scholar 

  145. Junge K, Wendt B, Shaikh N, Beller M (2010) Chem Commun 46:1769

    CAS  Google Scholar 

  146. Pehlivan L, Métay E, Laval S, Dayoub W, Demonchaux P, Mignani G, Lemaire M (2010) Tetrahedron Lett 51:1939

    CAS  Google Scholar 

  147. Pehlivan L, Métay E, Laval S, Dayoub W, Demonchaux P, Mignani G, Lemaire M (2011) Tetrahedron 67:1971

    CAS  Google Scholar 

  148. Bhor MD, Bhanushali MJ, Nandurkar NS, Bhanage BM (2008) Tetrahedron Lett 49:965

    CAS  Google Scholar 

  149. Fleischer S, Zhou S, Junge K, Beller M (2011) Chem Asian J 6:2240

    CAS  Google Scholar 

  150. Pagnoux-Ozherelyeva A, Pannetier N, Diagne Mbaye M, Gaillard S, Renaud JL (2012) Angew Chem Int Ed 51:4976

    CAS  Google Scholar 

  151. Moulin S, Dentel H, Pagnoux-Ozherelyeva A, Gaillard S, Poater A, Cavallo L, Lohier JF, Renaud JL (2013) Chem Eur J 19:17881

    CAS  Google Scholar 

  152. Enthaler S (2010) ChemCatChem 2:1411

    CAS  Google Scholar 

  153. Jaafar H, Li H, Misal Castro LC, Zheng J, Roisnel T, Dorcet V, Sortais JB, Darcel C (2012) Eur J Inorg Chem 3546

    Google Scholar 

  154. Li H, Achard M, Bruneau C, Sortais JB, Darcel C (2014) RSC Adv 4:25892

    CAS  Google Scholar 

  155. Zhou S, Junge K, Addis D, Das S, Beller M (2009) Angew Chem Int Ed 48:9507

    CAS  Google Scholar 

  156. Sunada Y, Kawakami H, Motoyama Y, Nagashima H (2009) Angew Chem Int Ed 48:9511

    CAS  Google Scholar 

  157. Tsutsumi H, Sunada Y, Nagashima H (2011) Chem Commun 47:6581

    CAS  Google Scholar 

  158. Bézier D, Venkanna GT, Sortais JB, Darcel C (2011) ChemCatChem 3:1747

    Google Scholar 

  159. Volkov A, Buitrago E, Adolfsson H (2013) Eur J Org Chem 2066

    Google Scholar 

  160. Blom B, Tan G, Enthaler S, Inoue S, Epping JD, Driess M (2013) J Am Chem Soc 135:18108

    CAS  Google Scholar 

  161. Zhou S, Addis D, Das S, Junge K, Beller M (2009) Chem Commun 4883

    Google Scholar 

  162. Das S, Wendt B, Moeller K, Junge K, Beller M (2012) Angew Chem Int Ed 51:1662

    CAS  Google Scholar 

  163. Bornschein C, Werkmeister S, Werndt B, Jiao H, Alberico E, Baumann W, Junge H, Junge K, Beller M (2014) Nat Commun 5:4111

    CAS  Google Scholar 

  164. Bézier D, Venkanna GT, Misal Castro LC, Zheng J, Sortais JB, Darcel C (2012) Adv Synth Catal 354:1879

    Google Scholar 

  165. Junge K, Wendt B, Zhou S, Beller M (2013) Eur J Org Chem 2061

    Google Scholar 

  166. Ruddy AJ, Kelly CM, Crawford SM, Wheaton CA, Sydora OL, Small BL, Stradiotto M, Turculet L (2013) Organometallics 32:5581

    CAS  Google Scholar 

  167. Das S, Li Y, Junge K, Beller M (2012) Chem Commun 48:10742

    CAS  Google Scholar 

  168. Li H, Misal Castro LC, Zheng J, Roisnel T, Dorcet V, Sortais JB, Darcel C (2013) Angew Chem Int Ed 52:8045

    CAS  Google Scholar 

  169. Cong C, Fujihara T, Terao J, Tsuji Y (2014) Catal Commun 50:25

    CAS  Google Scholar 

  170. Zell T, Ben-David Y, Milstein D (2014) Angew Chem Int Ed 53:4685

    CAS  Google Scholar 

  171. Werkmeister S, Junge K, Wendt B, Alberico E, Jiao H, Baumann W, Junge H, Gallou F, Beller M (2014) Angew Chem Int Ed. doi:10.1002/anie.201402542

    Google Scholar 

  172. Chakraborty S, Dai H, Bhattacharya P, Fairweather NT, Gibson MS, Krause JA, Guan H (2014) J Am Chem Soc. doi:10.1021/ja405034

    Google Scholar 

  173. Misal Castro LC, Li H, Sortais JB, Darcel C (2012) Chem Commun 48:10514

    CAS  Google Scholar 

  174. Pouessel J, Jacquet O, Cantat T (2013) ChemCatChem 5:3552

    CAS  Google Scholar 

  175. Quadrelli EA, Centi G, Duplan JL, Perathoner S (2011) ChemSusChem 4:1194

    CAS  Google Scholar 

  176. Wang W, Wang S, Ma X, Gong J (2011) Chem Soc Rev 40:3703

    CAS  Google Scholar 

  177. Jessop PG, Ikariya T, Noyori R (1995) Chem Rev 95:259

    CAS  Google Scholar 

  178. Leitner W (1995) Angew Chem Int Ed Engl 34:2207

    CAS  Google Scholar 

  179. Jessop PG, Joó F, Tai CC (2004) Coord Chem Rev 248:2425

    CAS  Google Scholar 

  180. Federsel C, Jackstell R, Beller M (2010) Angew Chem Int Ed 49:6254

    CAS  Google Scholar 

  181. Tai CC, Chang T, Roller B, Jessop PG (2003) Inorg Chem 42:7340

    CAS  Google Scholar 

  182. Federsel C, Boddien A, Jackstell R, Jennerjahn R, Dyson PJ, Scopelliti R, Laurenczy G, Beller M (2010) Angew Chem Int Ed 49:9777

    CAS  Google Scholar 

  183. Drake JL, Manna CM, Byers JA (2013) Organometallics 32:6891

    CAS  Google Scholar 

  184. Ziebart C, Federsel C, Anbarasan P, Jackstell R, Baumann W, Spannenberg A, Beller M (2012) J Am Chem Soc 134:20701

    CAS  Google Scholar 

  185. Boddien A, Mellmann D, Gärtner F, Jackstell R, Junge H, Dyson PJ, Laurenczy G, Ludwig R, Beller M (2011) Science 333:1733

    CAS  Google Scholar 

  186. Yang X (2013) Dalton Trans 42:11987

    CAS  Google Scholar 

  187. Langer R, Diskin-Posner Y, Leitus G, Shimon LJM, Ben-David Y, Milstein D (2011) Angew Chem Int Ed 50:9948

    CAS  Google Scholar 

  188. Yang X (2011) ACS Catal 1:849

    CAS  Google Scholar 

  189. Frogneux X, Jacquet O, Cantat T (2014) Catal Sci Technol 4:1529

    CAS  Google Scholar 

  190. Enthaler S (2011) ChemCatChem 3:666

    CAS  Google Scholar 

  191. Cardoso JMS, Royo B (2012) Chem Commun 48:4944

    CAS  Google Scholar 

  192. Burgess K, Ohlmeyer MJ (1991) Chem Rev 91:1179

    CAS  Google Scholar 

  193. Miyaura N (2001) In: Togni A, Grützmacher H (eds) Catalytic heterofunctionalization. Wiley-VCH, Weinheim, pp 1–46

    Google Scholar 

  194. Hartwig JF (2011) Chem Soc Rev 40:1992

    CAS  Google Scholar 

  195. Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF (2010) Chem Rev 110:890

    CAS  Google Scholar 

  196. Hall DG (2005) Boronic acids. Wiley-VCH, New York

    Google Scholar 

  197. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    CAS  Google Scholar 

  198. Doucet H (2008) Eur J Org Chem 2013

    Google Scholar 

  199. Jana R, Pathak TP, Sigman MS (2011) Chem Rev 111:1417

    CAS  Google Scholar 

  200. Brown JM (2005) In: Evans PA (ed) Modern rhodium-catalysed organic reactions. Wiley-VCH Verlag, Weinheim, pp 33–54

    Google Scholar 

  201. Coyne AG, Guiry PJ (2008) In: Andersson PG, Munslow IJ (eds) Modern reduction methods. Wiley-VCH Verlag, Weinheim, pp 65–86

    Google Scholar 

  202. Hartwig JF, Huber S (1993) J Am Chem Soc 115:4908

    CAS  Google Scholar 

  203. Waltz KM, He X, Muhoro C, Hartwig JF (1995) J Am Chem Soc 117:11357

    CAS  Google Scholar 

  204. Wu JY, Moreau B, Ritter T (2009) J Am Chem Soc 131:12915

    CAS  Google Scholar 

  205. Haberberger M, Enthaler S (2011) Chem Asian J 8:50

    Google Scholar 

  206. Rawat VS, Sreedhar B (2014) Synlett 1132

    Google Scholar 

  207. Zhang L, Peng D, Leng X, Huang Z (2013) Angew Chem Int Ed 52:3676

    CAS  Google Scholar 

  208. Obligacion JV, Chirik PJ (2013) Org Lett 15:2680

    CAS  Google Scholar 

  209. Greenhalgh MD, Thomas SP (2013) Chem Commun 49:11230

    CAS  Google Scholar 

  210. Zheng J, Sortais JB, Darcel C (2014) ChemCatChem 6:763

    CAS  Google Scholar 

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  1. UMR 6226 CNRS-Université de Rennes 1 “Institut des Sciences Chimiques de Rennes”, Team “Organometallics: Materials and Catalysis”, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 263 Avenue du Général Leclerc, 35042, Rennes Cedex, France

    Christophe Darcel & Jean-Baptiste Sortais

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  1. Christophe Darcel
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  2. Jean-Baptiste Sortais
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Correspondence to Christophe Darcel .

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  1. Dept. of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri, USA

    Eike Bauer

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Darcel, C., Sortais, JB. (2015). Iron-Catalyzed Reduction and Hydroelementation Reactions. In: Bauer, E. (eds) Iron Catalysis II. Topics in Organometallic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/3418_2015_104

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