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Synthesis 2011(11): 1678-1690  
DOI: 10.1055/s-0030-1260028
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Inexpensive Copper/Iron-Cocatalyzed Reactions

Yijin Sua, Wei Jiaa, Ning Jiao*a,b
a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Bejing 100191, P. R. of China
Fax: +86(10)82805297; e-Mail: jiaoning@bjmu.edu.cn;
b State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
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Publication History

Received 10 February 2011
Publication Date:
06 May 2011 (online)

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Inexpensive Copper/Iron-Cocatalyzed ReactionsSynthesis 2011; 2011(11): e1-e1
DOI: 10.1055/s-0030-1260050

Abstract

Compared with other transition metals, copper and iron salts are inexpensive and stable to air and moisture. Moreover, iron is considered as an environmentally friendly catalyst. Due to these benign characteristics, both copper and iron catalysis have been extensively­ investigated. More recently, inexpensive copper/iron-cocatalyzed reactions have presented an attractive prospect for organic synthesis. This review presents recent progress in copper/iron-cocatalyzed arylation, alkynylation, C-H functionalization, and conjugate addition reactions.

1 Introduction

2 Arylation Reactions

2.1 C-N Bond Formation

2.2 C-O Bond Formation

2.3 C-S Bond Formation

2.4 Summary

3 Alkynylation Coupling Reactions

3.1 Sonogashira-Type Reactions

3.2 Glaser-Type Coupling

4 C-H Functionalization

5 Conjugate Addition Reactions

6 Conclusion

Key words

copper - iron - cocatalysis

    References

  • For books and reviews, see:
  • 1a Tsuji J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis   Wiley; Chichester: 2000. 
    Google Scholar
  • 1b Topics in Organometallic Chemistry: Palladium in Organic Synthesis   Tsuji J. Springer; New York: 2005. 
    Google Scholar
  • 1c Metal-catalyzed Cross-coupling Reactions   de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 1d Transition Metals for Organic Synthesis   2nd ed.:  Beller M. Bolm C. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 1e Buchwald SL. Acc. Chem. Res.  2008,  41:  1439 
    Google Scholar
  • For books and reviews, see:
  • 2a Catalysis Without Precious Metals   Bullock RM. Wiley-VCH; Weinheim: 2010. 
    Google Scholar
  • 2b Daugulis O. Do H.-Q. Shabashov D. Acc. Chem. Res.  2009,  42:  1074 
    Google Scholar
  • 2c Evano G. Blanchard N. Toumi M. Chem. Rev.  2008,  108:  3054 
    Google Scholar
  • 2d Alexakis A. Backvall JE. Krause N. Pamies O. Dieguez M. Chem. Rev.  2008,  108:  2796 
    Google Scholar
  • 2e Dudnik AS. Gevorgyan V. Angew. Chem. Int. Ed.  2010,  49:  2096 
    Google Scholar
  • 2f Armstrong A. Collins JC. Angew. Chem. Int. Ed.  2010,  49:  2282 
    Google Scholar
  • For recent reviews, see:
  • 3a Bolm C. Legros J. Le Paih J. Zani L. Chem. Rev.  2004,  104:  6217 
    Google Scholar
  • 3b Fürstner A. Martin R. Chem. Lett.  2005,  34:  624 
    Google Scholar
  • 3c Enthaler S. Junge K. Beller M. Angew. Chem. Int. Ed.  2008,  47:  3317 
    Google Scholar
  • For recent reviews, see:
  • 4a Kunz K. Scholtz U. Ganzer D. Synlett  2003,  2428 
    Google Scholar
  • 4b Ley SV. Thomas AW. Angew. Chem. Int. Ed.  2003,  42:  5400 
    Google Scholar
  • 4c Schnürch M. Flasik R. Khan AF. Spina M. Mihovilovic MD. Stanetty P. Eur. J. Org. Chem.  2006,  3283 
    Google Scholar
  • 5 Taillefer M. Xia N. Ouali A. Angew. Chem. Int. Ed.  2007,  46:  934 
    CrossrefPubMedGoogle Scholar
  • 6 Jadhav VH. Dumbre DK. Phapale VB. Borate HB. Wakharkar RD. Catal. Commun.  2007,  8:  65 
    CrossrefGoogle Scholar
  • 7 Wang Z. Fu H. Jiang Y. Zhao Y. Synlett  2008,  2540 
    Article in Thieme ConnectGoogle Scholar
  • 8 Guo D. Huang H. Zhou Y. Xu J. Jiang H. Chen K. Liu H. Green Chem.  2010,  12:  276 
    CrossrefGoogle Scholar
  • 9 Wu X.-F. Darcel C. Eur. J. Org. Chem.  2009,  4753 
    Google Scholar
  • 10a Song R.-J. Deng C.-L. Xie Y.-X. Li J.-H. Tetrahedron Lett.  2007,  48:  7845 
    Google Scholar
  • 10b Lam PYS. Deudon S. Averill KM. Li R. He MY. DeShong P. Clark CG. J. Am. Chem. Soc.  2000,  122:  7600 
    Google Scholar
  • For recent reviews, see:
  • 11a Beletskaya IP. Cheprakov AV. Coord. Chem. Rev.  2004,  248:  2337 
    Google Scholar
  • 11b Monnier F. Taillefer M. Angew. Chem. Int. Ed.  2009,  48:  6954 
    Google Scholar
  • 12 Liu X. Zhang S. Synlett  2011,  268 
    Article in Thieme ConnectGoogle Scholar
  • For recent reviews and articles, see:
  • 13a Kondo T. Mitsudo T. Chem. Rev.  2000,  100:  3205 
    Google Scholar
  • 13b Jiang Z. She J. Lin X. Adv. Synth. Catal.  2009,  351:  2558 
    Google Scholar
  • 13c Zhang Y. Ngeow KC. Ying JY. Org. Lett.  2007,  9:  3495 
    Google Scholar
  • 13d Wu W.-Y. Wang J.-C. Tsai F.-Y. Green Chem.  2009,  11:  326 
    Google Scholar
  • 13e Wong YC. Jayanth TT. Cheng CH. Org. Lett.  2006,  8:  5613 
    Google Scholar
  • 13f Kabir MS. Lorenz M. Van Linn ML. Namjoshi OA. Ara S. Cook JM. J. Org. Chem.  2010,  75:  3626 
    Google Scholar
  • 14 Ku X. Huang H. Jiang H. Liu H. J. Comb. Chem.  2009,  11:  338 
    CrossrefGoogle Scholar
  • 15 For recent reviews, see: Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
    Google Scholar
  • 16 Volla CMR. Vogel P. Tetrahedron Lett.  2008,  49:  5961 
    CrossrefGoogle Scholar
  • 17 Mao J. Xie G. Wu M. Guo J. Ji S. Adv. Synth. Catal.  2008,  350:  2477 
    CrossrefGoogle Scholar
  • 18 Huang H. Jiang H. Chen K. Liu H. J. Org. Chem.  2008,  73:  9061 
    CrossrefGoogle Scholar
  • For books and articles, see :
  • 19a Taylor RJK. In Organocopper Reagents: A Practical Approach   Oxford University Press; New York: 1994. 
    Google Scholar
  • 19b Wang D. Li J. Li N. Gao T. Hou S. Chen B. Green Chem.  2010,  12:  45 
    Google Scholar
  • 20 Meng X. Li C. Han B. Wang T. Chen B. Tetrahedron  2010,  66:  4029 
    CrossrefGoogle Scholar
  • For recent reviews, see:
  • 21a Thansandote P. Lautens M. Chem. Eur. J.  2009,  15:  5874 
    Google Scholar
  • 21b Lyons TW. Sanford MS. Chem. Rev.  2010,  110:  1147 
    Google Scholar
  • 21c Chen X. Engle KM. Wang D.-H. Yu J.-Q. Angew. Chem. Int. Ed.  2009,  48:  5094 
    Google Scholar
  • 21d Ackermann L. Vicente R. Kapdi AR. Angew. Chem. Int. Ed.  2009,  48:  9792 
    Google Scholar
  • 21e Colby DA. Bergman RG. Ellman JA. Chem. Rev.  2010,  110:  624 
    Google Scholar
  • 21f Li B.-J. Yang S.-D. Shi Z.-J. Synlett  2008,  949 
    Google Scholar
  • 21g Kakiuchi F. Kochi T. Synthesis  2008,  3013 
    Google Scholar
  • 21h Giri R. Shi B.-F. Engle KM. Maugel N. Yu J.-Q. Chem. Soc. Rev.  2009,  38:  3242 
    Google Scholar
  • 22 Wang H. Wang Y. Peng C. Zhang J. Zhu Q. J. Am. Chem. Soc.  2010,  132:  13217 
    Google Scholar
  • 23 Dyadchenko VP. Dyadchenko MA. Okulov VN. Lemenovskii DA. J. Organomet. Chem.  2011,  696:  468 
    CrossrefGoogle Scholar
  • 24 Shirakawa E. Yamagami T. Kimura T. Yamaguchi S. Hayashi T. J. Am. Chem. Soc.  2005,  127:  17164 
    CrossrefGoogle Scholar
  • 25 Li S. Jia W. Jiao N. Adv. Synth. Catal.  2009,  351:  569 
    CrossrefGoogle Scholar
  • 26 Knöpfel TF. Carreira EM. J. Am. Chem. Soc.  2003,  125:  6054 
    CrossrefPubMedGoogle Scholar