Skip to main content
SpringerLink
Log in

Iron-Catalyzed C–H Bond Activation

  • Chapter
  • First Online:
C-H Bond Activation and Catalytic Functionalization II

Part of the book series: Topics in Organometallic Chemistry ((volume 56))

Abstract

Iron-catalyzed C–H bond activation followed by C–C bond formation has received much attention in recent years, motivated by the environmental and economical merits of iron, as well as the scientific challenge in controlling and understanding the reactivity of iron species. This review describes the utilization of iron as a catalyst for directed C–H bond activation, followed by C–C bond formation. Catalytic activation of C(sp2)-H and C(sp3-H) bonds, followed by oxidative reaction with nucleophiles, or reaction with electrophiles is described. Reactions of substrates possessing a directing group are mainly discussed, but other substrates are also presented. Carbon–heteroatom bond formation is also briefly discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Dyker G (ed) (2005) Handbook of C–H transformations. Wiley-VCH, Weinheim

    Google Scholar 

  2. Godula K, Sames D (2006) Science 312:67

    Article  CAS  Google Scholar 

  3. Gutekunst WR, Baran PS (2011) Chem Soc Rev 40:1976

    Article  CAS  Google Scholar 

  4. Wencel-Delord J, Glorius F (2013) Nat Chem 5:369

    Article  CAS  Google Scholar 

  5. Segawa Y, Maekawa T, Itami K (2015) Angew Chem Int Ed 54:66

    Article  CAS  Google Scholar 

  6. Nakamura E, Sato K (2011) Nat Mater 10:158

    Article  CAS  Google Scholar 

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

    Google Scholar 

  8. Bolm C (2009) Nat Chem 1:420

    Article  CAS  Google Scholar 

  9. Kulkarni A, Daugulis O (2009) Synthesis 4087

    Google Scholar 

  10. Sun C-L, Li B-J, Shi Z-J (2011) Chem Rev 111:1293

    Article  CAS  Google Scholar 

  11. Bauer I, Knölker H-J (2015) Chem Rev 115:3170

    Article  CAS  Google Scholar 

  12. Yoshikai N (2014) Iron-catalyzed cross-coupling reactions. In: Marek I, Rappoport Z (eds) The chemistry of organoiron compounds. Wiley, Chichester

    Google Scholar 

  13. Ambhaikar NB (2015) Iron-catalyzed C–H activation. In: Li JJ (ed) C–H bond activation in organic synthesis. CRC, Boca Raton

    Google Scholar 

  14. Mihovilovic MD, Schnürch M (2014) ChemCatChem 6:2194

    Article  CAS  Google Scholar 

  15. Su B, Cao Z-C, Shi Z-J (2015) Acc Chem Rev 48:886

    Article  CAS  Google Scholar 

  16. Nakamura E, Yoshikai N (2010) J Org Chem 75:6061

    Article  CAS  Google Scholar 

  17. Bagga MM, Pauson PL, Preston FJ, Reed RI (1965) Chem Commun 543

    Google Scholar 

  18. Baikie PE, Mills OS (1966) Chem Commun 707

    Google Scholar 

  19. Bagga MM, Flannigan WT, Knox GR, Pauson PL, Preston FJ, Reed RI (1968) J Chem Soc C 36

    Google Scholar 

  20. Alper H, Chan ASK (1971) Chem Commun 1203

    Google Scholar 

  21. Klein H-F, Camadanli S, Beck R, Leukel D, Flörke U (2005) Angew Chem Int Ed 44:975

    Article  CAS  Google Scholar 

  22. Camadanli S, Beck R, Flörke U, Klein H-F (2009) Organometallics 28:2300

    Article  CAS  Google Scholar 

  23. Norinder J, Matsumoto A, Yoshikai N, Nakamura E (2008) J Am Chem Soc 130:5858

    Article  CAS  Google Scholar 

  24. Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2009) Angew Chem Int Ed 48:2925

    Article  CAS  Google Scholar 

  25. Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2010) Synlett 313

    Google Scholar 

  26. Ilies L, Konno E, Chen Q, Nakamura E (2012) Asian J Org Chem 1:142

    Article  CAS  Google Scholar 

  27. Gu Q, Al Mamari HH, Graczyk K, Diers E, Ackermann L (2014) Angew Chem Int Ed 53:3868

    Article  CAS  Google Scholar 

  28. Yoshikai N, Asako S, Yamakawa T, Ilies L, Nakamura E (2011) Chem Asian J 6:3059

    Article  CAS  Google Scholar 

  29. Cahiez G, Chaboche C, Mahuteau-Betzer F, Ahr M (2005) Org Lett 7:1943

    Article  CAS  Google Scholar 

  30. Nagano T, Hayashi T (2005) Org Lett 7:491

    Article  CAS  Google Scholar 

  31. Sirois JJ, Davis R, DeBoef B (2014) Org Lett 16:868

    Article  CAS  Google Scholar 

  32. Simmons EM, Hartwig JF (2012) Angew Chem Int Ed 51:3066

    Article  CAS  Google Scholar 

  33. Bedford RB (2015) Acc Chem Rev 48:1485

    Article  CAS  Google Scholar 

  34. Ilies L, Asako S, Nakamura E (2011) J Am Chem Soc 133:7672

    Article  CAS  Google Scholar 

  35. Ilies L, Kobayashi M, Matsumoto A, Yoshikai N, Nakamura E (2012) Adv Synth Catal 354:593

    Article  CAS  Google Scholar 

  36. Bogdanovic B, Schwickardi M (2000) Angew Chem Int Ed 39:4610

    Article  CAS  Google Scholar 

  37. Czaplik WM, Mayer M, Jacobi von Wangelin A (2009) Angew Chem Int Ed 48:607

    Article  CAS  Google Scholar 

  38. Czaplik WM, Mayer M, Jacobi von Wangelin A (2011) ChemCatChem 3:135

    Article  CAS  Google Scholar 

  39. Kobayashi Y, Mizojiri R (1996) Tetrahedron Lett 37:8531

    Article  CAS  Google Scholar 

  40. Hatakeyama T, Hashimoto T, Kondo Y, Fujiwara Y, Seike H, Takaya H, Tamada Y, Ono T, Nakamura M (2010) J Am Chem Soc 132:10674

    Article  CAS  Google Scholar 

  41. Zaitsev VG, Shabashov D, Daugulis O (2005) J Am Chem Soc 127:13154

    Article  CAS  Google Scholar 

  42. Rouquet G, Chatani N (2013) Angew Chem Int Ed 52:11726

    Article  CAS  Google Scholar 

  43. Daugulis O, Roane J, Tran LD (2015) Acc Chem Res 48:1053

    Article  CAS  Google Scholar 

  44. Shang R, Ilies L, Asako S, Nakamura E (2014) J Am Chem Soc 136:14349

    Article  CAS  Google Scholar 

  45. Bedford RB, Hall MA, Hodges GR, Huwe M, Wilkinson MC (2009) Chem Commun 6430

    Google Scholar 

  46. Bedford RB, Gower NJ, Haddow MF, Harvey JN, Nunn J, Okopie RA, Sankey F (2012) Angew Chem Int Ed 51:5435

    Article  CAS  Google Scholar 

  47. Blanchard S, Derat E, Murr M, Fensterbank L, Malacria M, Mouries-Mansuy V (2012) Eur J Inorg Chem 376

    Google Scholar 

  48. Ilies L, Ichikawa S, Asako S, Matsubara T, Nakamura E (2015) Adv Synth Catal. doi:10.1002/adsc.201500276

    Google Scholar 

  49. Asako S, Ilies L, Nakamura E (2013) J Am Chem Soc 135:17755

    Article  CAS  Google Scholar 

  50. Asako S, Norinder J, Ilies L, Yoshikai N, Nakamura E (2014) Adv Synth Catal 356:1481

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  52. Ilies L, Matsubara T, Ichikawa S, Asako S, Nakamura E (2014) J Am Chem Soc 136:13126

    Article  CAS  Google Scholar 

  53. Monks BM, Fruchey ER, Cook SP (2014) Angew Chem Int Ed 53:11065

    Article  CAS  Google Scholar 

  54. Fruchey ER, Monks BM, Cook SP (2014) J Am Chem Soc 136:13130

    Article  CAS  Google Scholar 

  55. Wong MY, Yamakawa T, Yoshikai N (2015) Org Lett 17:442

    Article  CAS  Google Scholar 

  56. Gao K, Yoshikai N (2014) Acc Chem Res 47:1208

    Article  CAS  Google Scholar 

  57. Tolman CA, Ittel SD, English AD, Jesson JP (1978) J Am Chem Soc 100:4080

    Article  CAS  Google Scholar 

  58. Baker MV, Field LD (1986) J Am Chem Soc 108:7433

    Article  CAS  Google Scholar 

  59. Jones WD, Foster GP, Putinas JM (1987) J Am Chem Soc 109:5047

    Article  CAS  Google Scholar 

  60. Vallée F, Mousseau JJ, Charette AB (2010) J Am Chem Soc 132:1514

    Article  Google Scholar 

  61. Liu W, Cao H, Lei A (2010) Angew Chem Int Ed 49:2004

    Article  CAS  Google Scholar 

  62. Yanagisawa S, Itami K (2011) ChemCatChem 3:827

    Article  CAS  Google Scholar 

  63. Wen J, Qin S, Ma L-F, Dong L, Zhang J, Liu S-S, Duan Y-S, Chen S-Y, Hu C-W, Yu X-Q (2010) Org Lett 12:2694

    Article  CAS  Google Scholar 

  64. Wen J, Zhang J, Chen S-Y, Li J, Yu X-Q (2008) Angew Chem Int Ed 47:8897

    Article  CAS  Google Scholar 

  65. Singh PP, Aithagani SK, Yadav M, Singh VP, Vishwakarma RA (2013) J Org Chem 78:2639

    Article  CAS  Google Scholar 

  66. Uchiyama N, Shirakawa E, Nishikawa R, Hayashi T (2011) Chem Commun 47:11671

    Article  CAS  Google Scholar 

  67. Matsumoto A, Ilies L, Nakamura E (2011) J Am Chem Soc 133:6557

    Article  CAS  Google Scholar 

  68. Ilies L, Matsumoto A, Kobayashi M, Yoshikai N, Nakamura E (2012) Synlett 23:2381

    Article  CAS  Google Scholar 

  69. Hojo M, Murakami Y, Aihara H, Sakuragi R, Baba Y, Hosomi A (2001) Angew Chem Int Ed 40:621

    Article  CAS  Google Scholar 

  70. Shirakawa E, Yamagami T, Kimura T, Yamaguchi S, Hayashi T (2005) J Am Chem Soc 127:17164

    Article  CAS  Google Scholar 

  71. Zhang D, Ready JM (2006) J Am Chem Soc 128:15050

    Article  CAS  Google Scholar 

  72. Yamagami T, Shintani R, Shirakawa E, Hayashi T (2007) Org Lett 9:1045

    Article  CAS  Google Scholar 

  73. Shirakawa E, Ikeda D, Masui S, Yoshida M, Hayashi T (2012) J Am Chem Soc 134:272

    Article  CAS  Google Scholar 

  74. Sunada Y, Soejima H, Nagashima H (2014) Organometallics 33:5936

    Article  CAS  Google Scholar 

  75. Ito J, Hosokawa S, Khalid HB, Nishiyama H (2015) Organometallics 34:1377

    Article  CAS  Google Scholar 

  76. Hatanaka T, Ohki Y, Tatsumi K (2010) Chem Asian J 5:1657

    Article  CAS  Google Scholar 

  77. Yan G, Jiang Y, Kuang C, Wang S, Liu H, Zhang Y, Wang J (2010) Chem Commun 46:3170

    Article  CAS  Google Scholar 

  78. Mazzacano TJ, Mankad NP (2013) J Am Chem Soc 135:17258

    Article  CAS  Google Scholar 

  79. Dombray T, Werncke CG, Jiang S, Grellier M, Vendier L, Bontemps S, Sortais J-B, Sabo-Etienne S, Darcel C (2015) J Am Chem Soc 137:4062

    Article  CAS  Google Scholar 

  80. Xu G, Sun H, Li X (2009) Organometallics 28:6090

    Article  CAS  Google Scholar 

  81. Ohki Y, Hatanaka T, Tatsumi K (2008) J Am Chem Soc 130:17174

    Article  CAS  Google Scholar 

  82. Shang R, Ilies L, Matsumoto A, Nakamura E (2013) J Am Chem Soc 135:6030

    Article  CAS  Google Scholar 

  83. Waltz KM, Hartwig JF (1997) Science 277:211

    Article  CAS  Google Scholar 

  84. Waltz KM, Hartwig JF (2000) J Am Chem Soc 122:11358

    Article  CAS  Google Scholar 

  85. Yoshikai N, Mieczkowski A, Matsumoto A, Ilies L, Nakamura E (2010) J Am Chem Soc 132:5568

    Article  CAS  Google Scholar 

  86. Singh PP, Gudup S, Ambala S, Singh U, Dadhwal S, Singh B, Sawant SD, Vishwakarma RA (2011) Chem Commun 47:5852

    Article  CAS  Google Scholar 

  87. Singh PP, Gudup S, Aruri H, Singh U, Ambala S, Yadav M, Sawant SD, Vishwakarma RA (2012) Org Biomol Chem 10:1587

    Article  CAS  Google Scholar 

  88. Sekine M, Ilies L, Nakamura E (2013) Org Lett 15:714

    Article  CAS  Google Scholar 

  89. Li C-J (2009) Acc Chem Res 42:335

    Article  CAS  Google Scholar 

  90. Li Z (2014) Org Chem Front 1:194

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, The University of Tokyo, School of Science, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan

    Laurean Ilies & Eiichi Nakamura

Authors
  1. Laurean Ilies
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Eiichi Nakamura
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Laurean Ilies or Eiichi Nakamura .

Editor information

Editors and Affiliations

  1. Université de Rennes, Rennes, France

    Pierre H. Dixneuf

  2. Université de Rennes, Rennes, France

    Henri Doucet

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Ilies, L., Nakamura, E. (2015). Iron-Catalyzed C–H Bond Activation. In: Dixneuf, P., Doucet, H. (eds) C-H Bond Activation and Catalytic Functionalization II. Topics in Organometallic Chemistry, vol 56. Springer, Cham. https://doi.org/10.1007/3418_2015_129

Download citation

Publish with us

Policies and ethics

Search

Navigation