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Iron Catalysis II pp 83–144Cite as

Iron-Catalyzed Carbon–Nitrogen, Carbon–Phosphorus, and Carbon–Sulfur Bond Formation and Cyclization Reactions

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

Abstract

The formation of carbon–heteroatom bonds (C–X bonds with X=N, S, P) upon addition of X-nucleophiles or X-electrophiles to unsaturated alkynes and alkenes, cross-coupling reactions, cycloadditions, tandem or consecutive reactions, or C–H functionalization is an attractive strategy in organic synthesis and is an intensive research area. Many organometallic species, more specifically palladium, nickel, and rhodium complexes, have paved the way to useful synthetic applications in this field. This chapter will cover iron-catalyzed bond-forming reactions between carbon and a heteroatom.

Keywords

  • Iron catalysis
  • C–X bond formation
  • Cross-coupling reactions
  • Cycloaddition
  • C–H functionalization
  • Addition reactions

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Fig. 1
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Abbreviations

AIBN:

Azobisisobutyronitrile

BINAP:

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

cod:

1,5-Cyclooctadiene

DCIB:

1,2-Dichloroisobutane

DDQ:

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DMEDA:

N,N′-Dimethylethylenediamine

DMSO:

Dimethyl sulfoxide

dppe:

1,2-Bis(diphenylphosphino)ethane

dppf:

1,1′-Bis(diphenylphosphino)ferrocene

dppp:

1,3-Bis(diphenylphosphino)propane

DTBP:

Di-tert-butyl peroxide

4-F-dppbz:

Bis(4-fluorophenyl)phosphinobenzene

HDA:

Hetero-Diels–Alder reaction

HMDS:

Bis(trimethylsilyl)amine

NBS:

N-Bromosuccinimide

Pc:

Phthalocyaninato

TBHP:

tert-Butyl hydroperoxide, tBuOOH

TEMPO:

(2,2,6,6-Tetramethylpiperidin-1-yl)oxyl

terpy:

Terpyridine ligand

triflate:

OTf, Trifluoromethanesulfonate, CF3SO3 −

TMSCl:

Trimethylsilyl chloride

TPP:

Tetraphenylporphyrin

TTN:

Total turnover number

References

  1. Bruneau C (2013) Top Organomet Chem 43:203

    CAS  Google Scholar 

  2. Evano G, Gaumont A-C, Alayrac C, Wrona IE, Giguere JR, Delacroix O, Bayle A, Jouvin K, Theunissen C, Gatignol J, Silvanus AC (2014) Tetrahedron 70:1529

    CAS  Google Scholar 

  3. Chemler SR, Bovino MT (2013) ACS Catal 3:1076

    CAS  Google Scholar 

  4. Hesp KD (2014) Angew Chem Int Ed 53:2034

    CAS  Google Scholar 

  5. Yim JC-H, Schafer LL (2014) Eur J Org Chem 6825

    Google Scholar 

  6. Evano G, Toumi M, Coste A (2009) Chem Commun 2009:4166

    Google Scholar 

  7. Li Y-M, Yang S-D (2013) Synlett 1739

    Google Scholar 

  8. Rossi R, Bellina F, Lessi M (2010) Synthesis 4131

    Google Scholar 

  9. Stanley LM, Sibi MP (2008) Chem Rev 108:2887

    CAS  Google Scholar 

  10. Adrio J, Carretero JC (2011) Chem Commun 47:6784

    CAS  Google Scholar 

  11. Chopade PR, Louie J (2006) Adv Synth Catal 348:2307

    CAS  Google Scholar 

  12. Neely JM, Rovis T (2014) Org Chem Front 1:1010

    CAS  Google Scholar 

  13. Aubin Y, Fischmeister C, Thomas CM, Renaud J-L (2010) Chem Soc Rev 39:4130

    CAS  Google Scholar 

  14. Evano G, Blanchard N, Toumi M (2008) Chem Rev 108:3054

    CAS  Google Scholar 

  15. Surry DS, Buchwald SL (2011) Chem Sci 2:27

    CAS  Google Scholar 

  16. Surry DS, Buchwald SL (2010) Chem Sci 1:13

    CAS  Google Scholar 

  17. Taillefer M, Xia N, Ouali A (2007) Angew Chem Int Ed 46:934

    CAS  Google Scholar 

  18. Guo D, Huang H, Xu J, Jiang H, Liu H (2008) Org Lett 10:4513

    CAS  Google Scholar 

  19. Suwiński J, Świerczek K (2001) Tetrahedron 57:1639

    Google Scholar 

  20. Teo YC (2009) Adv Synth Catal 351:720

    CAS  Google Scholar 

  21. Lee HW, Chan ASC, Kwong FY (2009) Tetrahedron Lett 50:5868

    CAS  Google Scholar 

  22. Mao J, Xie G, Zhan J, Hua Q, Shi D (2009) Adv Synth Catal 351:1268

    CAS  Google Scholar 

  23. Nakamura Y, Ilies L, Nakamura E (2011) Org Lett 13:5998

    CAS  Google Scholar 

  24. Hatakeyama T, Imayoshi R, Yoshimoto Y, Ghorai SK, Jin M, Takaya H, Norisuye K, Sohrin Y, Nakamura M (2012) J Am Chem Soc 134:20262

    CAS  Google Scholar 

  25. Johannsen M, Jørgensen KA (1998) Chem Rev 98:1689

    CAS  Google Scholar 

  26. Plietker B (2006) Angew Chem Int Ed 45:6053

    CAS  Google Scholar 

  27. Guérinot A, Serra-Muns A, Gnamm C, Bensoussan C, Reymond S, Cossy J (2010) J Org Lett 12:1808

    Google Scholar 

  28. Wang Z, Li S, Yu H, Wang Y, Sun X (2012) J Org Chem 77:8615

    CAS  Google Scholar 

  29. Kozhushkov SI, Potukuchi HK, Ackermann L (2013) Catal Sci Technol 3:562

    CAS  Google Scholar 

  30. Mousseau JJ, Charette AB (2013) Acc Chem Res 46:412

    CAS  Google Scholar 

  31. Huang Z, Dong G (2014) Tetrahedron Lett 55:5869

    CAS  Google Scholar 

  32. Ferreira EM (2014) Nature Chem 6:94

    CAS  Google Scholar 

  33. Yu D-G, de Azambuja F, Glorius F (2014) Angew Chem Int Ed 53:7710

    CAS  Google Scholar 

  34. Yeung CS, Dong VM (2011) Chem Rev 111:1215

    CAS  Google Scholar 

  35. Wu Y, Wang J, Mao F, Kwong FY (2014) Chem Asian J 9:26

    CAS  Google Scholar 

  36. Jia F, Li Z (2014) Org Chem Front 1:194

    CAS  Google Scholar 

  37. Huang D, Wang H, Xue F, Shi Y (2011) J Org Chem 76:7269

    CAS  Google Scholar 

  38. Murru S, Srivastava RS (2014) Eur J Org Chem 2174

    Google Scholar 

  39. Murru S, Gallo AA, Srivastava RS (2012) J Org Chem 77:7119

    CAS  Google Scholar 

  40. Xia Q, Chen W, Qiu H (2011) J Org Chem 76:7577

    CAS  Google Scholar 

  41. Cheng Y, Dong W, Wang L, Parthasarathy K, Bolm C (2014) Org Lett 16:2000

    CAS  Google Scholar 

  42. Chen D, Pan F, Gao J, Yang J (2013) Synlett 2085

    Google Scholar 

  43. Sun M, Zhang T, Bao W (2014) Tetrahedron Lett 55:893

    CAS  Google Scholar 

  44. Karthikeyan I, Sekar G (2014) Eur J Org Chem 8055

    Google Scholar 

  45. Matsubara T, Asako S, Ilies L, Nakamura E (2014) J Am Chem Soc 136:646

    CAS  Google Scholar 

  46. Correa A, García Mancheño O, Bolm C (2008) Chem Soc Rev 37:1108

    CAS  Google Scholar 

  47. Zhang L, Deng L (2012) Chinese Sci Bull 57:2352

    CAS  Google Scholar 

  48. Chow TWS, Chen GQ, Liu Y, Zhou CY, Che CM (2012) Pure Appl Chem 84:1685

    CAS  Google Scholar 

  49. Liu Y, Che CM (2010) Chem Eur J 16:10494

    CAS  Google Scholar 

  50. Hennessy ET, Liu RY, Iovan DA, Duncan RA, Betley TA (2014) Chem Sci 5:1526

    CAS  Google Scholar 

  51. Paradine SM, White CM (2012) J Am Chem Soc 134:2036

    CAS  Google Scholar 

  52. Liu P, Wong EL-M, Yuen AW-H, Che C-M (2008) Org Lett 10:3275

    CAS  Google Scholar 

  53. Liu Y, Guan X, Wong EL-M, Liu P, Huang JS, Che CM (2013) J Am Chem Soc 135:7194

    CAS  Google Scholar 

  54. Mansuy D, Mahy JP, Dureault A, Bedi G, Battioni PJ (1984) Chem Soc Chem Commun 1161

    Google Scholar 

  55. Breslow R, Gellman SHJ (1982) Chem Soc Chem Commun 1400

    Google Scholar 

  56. Nam W (2007) Acc Chem Res 40:522

    CAS  Google Scholar 

  57. Sorokin AB (2013) Chem Rev 113:8152

    CAS  Google Scholar 

  58. Gross Z, Gray HB (2004) Adv Synth Catal 346:165

    CAS  Google Scholar 

  59. McDonald AR, Que L Jr (2013) Coord Chem Rev 257:414

    CAS  Google Scholar 

  60. Talsi EP, Bryliakov KP (2012) Coord Chem Rev 256:1418

    CAS  Google Scholar 

  61. de Visser SP, Rohde J-U, Lee Y-M, Cho J, Nam W (2013) Coord Chem Rev 257:381

    Google Scholar 

  62. King ER, Hennessy ET, Betley TA (2011) J Am Chem Soc 133:4917

    CAS  Google Scholar 

  63. King ER, Betley TA (2009) Inorg Chem 48:2361

    CAS  Google Scholar 

  64. Liu Y, Wei J, Che CM (2010) Chem Commun 46:6926

    CAS  Google Scholar 

  65. Li J, Wu C, Zhang Q, Yan B (2013) Dalton Trans 42:14369

    CAS  Google Scholar 

  66. Bonnamour J, Bolm C (2011) Org Lett 13:2012

    CAS  Google Scholar 

  67. Shen M, Driver TG (2008) Org Lett 10:3367

    CAS  Google Scholar 

  68. Hennessy ET, Betley TA (2013) Science 340:591

    CAS  Google Scholar 

  69. Nguyen Q, Nguyen T, Driver TG (2013) J Am Chem Soc 135:620

    CAS  Google Scholar 

  70. McIntosh JA, Coelho PS, Farwell CC, Wang ZJ, Lewis JC, Brown TR, Arnold FH (2013) Angew Chem Int Ed 52:9309

    CAS  Google Scholar 

  71. Singh R, Bordeaux M, Fasan R (2014) ACS Catal 4:546

    CAS  Google Scholar 

  72. Imhof W, Anders E, Göbel A, Görls H (2003) Chem Eur J 9:1166

    CAS  Google Scholar 

  73. Imhof W, Anders E (2004) Chem Eur J 10:5717

    CAS  Google Scholar 

  74. Driller KM, Klein H, Jackstell R, Beller M (2009) Angew Chem Int Ed 48:6041

    CAS  Google Scholar 

  75. Prateeptongkum S, Driller KM, Jackstell R, Spannenberg A, Beller M (2010) Chem Eur J 16:9606

    CAS  Google Scholar 

  76. Mathur P, Joshi RK, Rai DK, Jha B, Mobin SM (2012) Dalton Trans 41:5045

    CAS  Google Scholar 

  77. Das B, Reddy GC, Balasubramanyam P, Veeranjaneyulu B (2010) Synlett 2010:1625

    Google Scholar 

  78. Fan JM, Gao LF, Wang ZY (2009) Chem Commun 5021

    Google Scholar 

  79. Viton F, Bernardinelli G, Kündig EP (2002) J Am Chem Soc 124:4968

    CAS  Google Scholar 

  80. Badoiu A, Bernardinelli G, Mareda J, Kündig EP, Viton F (2008) Chem Asian J 3:1298

    CAS  Google Scholar 

  81. Wu H, Wang B, Liu H, Wang L (2011) Tetrahedron 67:1210

    CAS  Google Scholar 

  82. Wang M, Liu X, He P, Lin L, Feng X (2013) Chem Commun 49:2572

    CAS  Google Scholar 

  83. Sun B, Ma Q, Wang Y, Zhao Y, Liao P, Bi X (2014) Eur J Org Chem 75:52

    Google Scholar 

  84. Sharpless KB, Chong AO, Oshima J (1976) J Org Chem 41:177

    Google Scholar 

  85. Alexanian EJ, Lee C, Sorensen EJ (2005) J Am Chem Soc 127:7690

    CAS  Google Scholar 

  86. Szolcsányi P, Gracza T (2005) Chem Commun 3948

    Google Scholar 

  87. Noack M, Göttlich R (2002) Chem Commun 536

    Google Scholar 

  88. Williamson KS, Yoon TP (2010) J Am Chem Soc 132:4570

    CAS  Google Scholar 

  89. Michaelis DJ, Shaffer CJ, Yoon TP (2007) J Am Chem Soc 129:1866

    CAS  Google Scholar 

  90. Michaelis DJ, Ischay MA, Yoon TP (2008) J Am Chem Soc 130:6610

    CAS  Google Scholar 

  91. Michaelis DJ, Williamson KS, Yoon TP (2009) Tetrahedron 65:5118

    CAS  Google Scholar 

  92. Benkovics T, Du J, Guzei I, Yoon TP (2009) J Org Chem 74:5545

    CAS  Google Scholar 

  93. Williamson KS, Yoon TP (2012) J Am Chem Soc 134:12370

    CAS  Google Scholar 

  94. Ren Q, Guan S, Shen X, Fang J (2014) Organometallics 33:1423

    CAS  Google Scholar 

  95. Liu G-S, Zhang Y-Q, Yuan Y-A, Xu H (2013) J Am Chem Soc 135:3343

    CAS  Google Scholar 

  96. Zhang Y-Q, Yuan Y-A, Liu G-S, Xu H (2013) Org Lett 15:3910

    CAS  Google Scholar 

  97. Bach T, Schlummer B, Harms K (2000) Chem Commun 287

    Google Scholar 

  98. Bach T, Schlummer B, Harms K (2001) Chem Eur J 7:2581

    CAS  Google Scholar 

  99. Bach T, Schlummer B, Harms K (2000) Synlett 1330

    Google Scholar 

  100. Michaux J, Terrasson V, Marque S, Wehbe J, Prim D, Campagne J-M (2007) Eur J Org Chem 2601

    Google Scholar 

  101. Cheng X, Xia Y, Xei H, Xu B, Zhang C, Li Y, Qian G, Zhang X, Li K, Li W (2008) Eur J Org Chem 1929

    Google Scholar 

  102. Dal Zotto C, Michaux J, Zarate-Ruiz A, Gayon E, Campagne J-M, Terrasson V, Pieters G, Virieux D, Gaucher A, Prim D (2011) J Organomet Chem 696:296

    CAS  Google Scholar 

  103. Komeyama K, Morimoto T, Takaki K (2006) Angew Chem Int Ed 45:2938

    CAS  Google Scholar 

  104. Bernoud E, Oulié P, Guillot R, Mellah M, Hannedouche J (2014) Angew Chem Int Ed 53:4930

    CAS  Google Scholar 

  105. Hsieh THH, Dong VM (2009) Tetrahedron 65:3062

    CAS  Google Scholar 

  106. For selected examples of drugs containing ring pyridines, see: Kodimuthali A, Lal Jabaris SS, Pal M (2008) J Med Chem 51:5471

    Google Scholar 

  107. For reviews on pyridine as ligand in homogeneous catalysis, see: Gibson VC, Redshaw C, Solan GA (2007) Chem Rev 107:1745

    Google Scholar 

  108. Wurz RP (2007) Chem Rev 107:5570

    CAS  Google Scholar 

  109. For a recent review on pyridine synthesis, see: Hill MD (2010) Chem Eur J 16:12052

    Google Scholar 

  110. For recent reviews on transition metal-catalysed [2+2+2] cycloaddition for pyridine synthesis, see: Weding N, Hapke M (2011) Chem Soc Rev 40:4525

    Google Scholar 

  111. Sugiyama Y-K, Okamoto S (2011) Synthesis 2247

    Google Scholar 

  112. Shaaban MR, El-Sayed R, Elwahy AHM (2011) Tetrahedron 67:6095

    CAS  Google Scholar 

  113. Domίnguez G, Pérez-Castells J (2011) Chem Soc Rev 40:3430

    Google Scholar 

  114. Broere DLJ, Ruijter E (2012) Synthesis 2639

    Google Scholar 

  115. For applications of the metal-catalysed [2+2+2] cycloaddition reaction in natural product synthesis, see: Witulski B, Grand J (2013) in Application to the Synthesis of Natural Products, in Transition-Metal-Mediated Aromatic Ring Construction (ed K. Tanaka), John Wiley & Sons, Inc., Hoboken, NJ, USA. doi: 10.1002/9781118629871.ch7

    Google Scholar 

  116. For a recent example, see: Xu F, Wang C, Li X, Wan B (2012) ChemSusChem 5:854 and references cited therein

    Google Scholar 

  117. Komine Y, Tanaka K (2010) Org Lett 12:1312 and references cited therein

    Google Scholar 

  118. Onodera G, Shimizu Y, Kimura J-n, Kobayashi J, Ebihara Y, Kondo K, Sakata K, Takeuchi R (2012) J Am Chem Soc 134:10515

    CAS  Google Scholar 

  119. For a selected recent example, see: Garcia P, Evanno Y, George P, Sevrin M, Ricci G, Malacria M, Aubert C, Gandon V (2011) Org Lett 13:2030 and references cited therein

    Google Scholar 

  120. Sugiyama Y-k, Okamoto S (2011) Synthesis 2247 and references cited therein

    Google Scholar 

  121. Zou Y, Liu QY, Deiters A (2011) Org Lett 13:4352 and references cited therein

    Google Scholar 

  122. Weding N, Jackstell R, Jiao H, Spannenberg A, Hapke M (2011) Adv Synth Catal 353:3423 and references cited therein

    Google Scholar 

  123. Knoch F, Kremer F, Schmidt U, Zenneck U, Le Floch P, Mathey F (1996) Organometallics 15:2713

    CAS  Google Scholar 

  124. Wang C, Li X, Wu F, Wan B (2011) Angew Chem Int Ed 50:7162

    CAS  Google Scholar 

  125. D’Souza BR, Lane TK, Louie J (2011) J Org Lett 13:2936

    Google Scholar 

  126. For reviews on non-innocent ligands and related complexes, see: van der Vlugt JI (2012) Eur J Inorg Chem 363

    Google Scholar 

  127. Blanchard S, Derat E, Desage-El Murr M, Fensterbank L, Malacria M, Mouriès-Mansuy V (2012) Eur J Inorg Chem 376

    Google Scholar 

  128. Schauer PA, Low PJ (2012) Eur J Inorg Chem 390

    Google Scholar 

  129. Schneider S, Meiners J, Askevold B (2012) Eur J Inorg Chem 412

    Google Scholar 

  130. Lyaskovskyy V, de Bruin B (2012) ACS Catal 2:270

    CAS  Google Scholar 

  131. Chirik PJ, Wieghardt KW (2010) Science 327:794

    CAS  Google Scholar 

  132. Caulton KG (2012) Eur J Inorg Chem 435

    Google Scholar 

  133. Lane TK, D’Souza BR, Louie J (2012) J Org Chem 77:7555

    CAS  Google Scholar 

  134. Wang C, Wang D, Xu F, Pan B, Wan B (2013) J Org Chem 78:3065

    CAS  Google Scholar 

  135. Lane TK, Nguyen MH, D’Souza BR, Spahin NA, Louie J (2013) J Chem Commun 49:7735

    CAS  Google Scholar 

  136. Ferré K, Toupet L, Guerchais V (2002) Organometallics 21:2578

    Google Scholar 

  137. Richard V, Ipouck M, Mérel DS, Gaillard S, Whitby RJ, Witulski B, Renaud J-L (2014) Chem Commun 50:593

    CAS  Google Scholar 

  138. Cao K, Zhang FM, Tu YQ, Zhuo XT, Fan CA (2009) Chem Eur J 15:6332

    CAS  Google Scholar 

  139. Ertürk E, Demir AS (2008) ARKIVOC 160

    Google Scholar 

  140. Plancq B, Ollevier T (2012) Chem Commun 48:3806

    CAS  Google Scholar 

  141. Allen CL, Lapkin AA, Williams JMJ (2009) Tetrahedron Lett 50:4262

    CAS  Google Scholar 

  142. Wang F, Liu H, Fu H, Jiang Y, Zhao Y (2009) Adv Synth Catal 351:246

    CAS  Google Scholar 

  143. Anxionnat B, Guérinot A, Reymond S, Cossy J (2009) Tetrahedron Lett 50:3470

    CAS  Google Scholar 

  144. Chen GQ, Xu ZJ, Liu Y, Zhou CY, Che CM (2011) Synlett 1174

    Google Scholar 

  145. Qin C, Zhou W, Chen F, Ou Y, Jiao N (2011) Angew Chem Int Ed 50:12595

    CAS  Google Scholar 

  146. Evano G, Jouvin K, Coste A (2013) Synthesis 17

    Google Scholar 

  147. Yao B, Liang Z, Niu T, Zhang Y (2009) J Org Chem 74:4630

    CAS  Google Scholar 

  148. Yan W, Ye X, Weise K, Petersen JL, Shi X (2012) Chem Commun 48:3521

    CAS  Google Scholar 

  149. Eisenberger P, Gishig S, Togni A (2006) Chem Eur J 12:2579

    CAS  Google Scholar 

  150. Deng QH, Bleith T, Wadepohl H, Gade LH (2013) J Am Chem Soc 135:5356

    CAS  Google Scholar 

  151. Deng QH, Wadepohl H, Gade LH (2011) Chem Eur J 17:14922

    Google Scholar 

  152. Bach T, Körber C (2000) J Org Chem 65:2358

    CAS  Google Scholar 

  153. Bacci JP, Greenman KL, Van Vranken DL (2003) J Org Chem 68:4955

    CAS  Google Scholar 

  154. Prateeptongkum S, Jovel I, Jackstell R, Vogl N, Xeckbecker C, Beller M (2009) Chem Commun 1990

    Google Scholar 

  155. Chu C-M, Huang W-J, Lu C, Wu P, Liu J-T, Yao C-F (2006) Tetrahedron Lett 47:7375

    CAS  Google Scholar 

  156. Kawatsura M, Komatsu Y, Yamamoto M, Hayase S, Itoh T (2007) Tetrahedron Lett 48:6480

    CAS  Google Scholar 

  157. White JD, Shaw S (2014) Chem Sci 5:2200

    CAS  Google Scholar 

  158. Alt I, Rohse P, Plietker B (2013) ACS Catal 3:3002

    CAS  Google Scholar 

  159. Shen T, Yuan Y, Song S, Jiao N (2014) Chem Commun 50:4115

    CAS  Google Scholar 

  160. Correa A, Carril M, Bolm C (2008) Angew Chem Int Ed 47:2880

    CAS  Google Scholar 

  161. Wu W-Y, Wang J-C, Tsai F-Y (2009) Green Chem 11:326

    CAS  Google Scholar 

  162. Lin Y-Y, Wang Y-J, Lin C-H, Cheng J-H, Lee C-F (2012) J Org Chem 77:6100

    CAS  Google Scholar 

  163. Zeng X, Ilies L, Nakamura E (2012) Org Lett 14:954

    CAS  Google Scholar 

  164. Iwasaki M, Fujii T, Yamamoto A, Nakajima K, Nishihara Y (2014) Chem Asian J 9:58

    CAS  Google Scholar 

  165. Liu S, Tang L, Chen H, Zhao F, Deng G-J (2014) Org Biomol Chem 12:6076

    CAS  Google Scholar 

  166. Holzwarth MS, Frey W, Plietker B (2011) Chem Commun 47:11113

    CAS  Google Scholar 

  167. Jegelka M, Plietker B (2009) Org Lett 11:3462

    CAS  Google Scholar 

  168. Qiu J-W, Zhang X-G, Tang R-Y, Zhong P, Li J-H (2009) Adv Synth Catal 351:2319

    CAS  Google Scholar 

  169. Khemnar AB, Bhanage BM (2014) RSC Adv 4:8939

    CAS  Google Scholar 

  170. Holzwarth MS, Alt I, Plietker B (2012) Angew Chem Int Ed 51:5351

    CAS  Google Scholar 

  171. Carter DS, Van Vranken DL (2000) Org Lett 2:1303

    CAS  Google Scholar 

  172. Prabharasuth R, Van Vranken DL (2001) J Org Chem 66:5256

    CAS  Google Scholar 

  173. Shi X, Ren X, Ren Z, Li J, Wang Y, Yang S, Gu J, Gao Q, Huang G (2014) Eur J Org Chem 5083

    Google Scholar 

  174. Kazankova MA, Efimova IV, Kochetkov AN, Afanas’ev VV, Beletskaya IP, Dixneuf PH (2001) Synlett 497

    Google Scholar 

  175. Kazankova MA, Efimova IV, Kochetkov AN, Afanas’ev VV, Beletskaya IP (2002) Russ J Org Chem 38:1465

    CAS  Google Scholar 

  176. Alonso F, Beletskaya IP, Yus M (2004) Chem Rev 104:3079

    CAS  Google Scholar 

  177. Delacroix O, Gaumont AC (2005) Curr Org Chem 9:1851

    CAS  Google Scholar 

  178. Mimeau D, Delacroix O, Gaumont AC (2003) Chem Commun 2928

    Google Scholar 

  179. Kamitani M, Itazaki M, Tamiya C, Nakazawa H (2012) J Am Chem Soc 134:11932

    CAS  Google Scholar 

  180. Rommel S, Dieskau AP, Plietker B (2013) Eur J Org Chem 2013:1790

    CAS  Google Scholar 

  181. Taniguchi T, Idota A, Yokoyama S-i, Ishibashi H (2011) Tetrahedron Lett 52:4768

    CAS  Google Scholar 

  182. Boobalan R, Chen C (2013) Adv Synth Catal 355:3443

    CAS  Google Scholar 

  183. Wu J, Sun W, Wang W-Z, Xia H-G (2006) Chin J Chem 24:1054

    CAS  Google Scholar 

  184. Reddy BVS, Krishna AS, Ganesh AV, Kumar GGKSN (2011) Tetrahedron Lett 52:1359

    CAS  Google Scholar 

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  1. Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507, Normandie University, University of Caen Basse Normandie, 14050, Caen, France

    Jean-Luc Renaud & Sylvain Gaillard

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  1. Jean-Luc Renaud
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  2. Sylvain Gaillard
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Correspondence to Jean-Luc Renaud .

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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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Renaud, JL., Gaillard, S. (2015). Iron-Catalyzed Carbon–Nitrogen, Carbon–Phosphorus, and Carbon–Sulfur Bond Formation and Cyclization Reactions. In: Bauer, E. (eds) Iron Catalysis II. Topics in Organometallic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/3418_2015_103

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