Inexpensive Copper/Iron-Cocatalyzed Reactions

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