Recent advances in mechanistic studies on Ni catalyzed cross-coupling reactions

doi:10.1016/S1872-2067(14)60217-5

Abstract

Abstract:

A variety of Ni catalyzed cross-coupling reactions have emerged as efficient new methods for the construction of C-C bonds, and many mechanistic studies have been conducted to understand the factors controlling the reactivity and selectivity of Ni catalyzed reactions. The mechanisms of Ni catalyzed reactions are often very different from the corresponding Pd catalyzed processes because radical or bimetallic pathways are frequently involved in Ni catalyzed cross-coupling reactions. This review summarized recent advances in the mechanism of Ni catalyzed cross-coupling reactions. These are important for the development of new Ni catalyzed cross-coupling reactions with improved efficiency and selectivity.

Key words: Nickel, Homogeneous catalysis, Cross-coupling, C-C bond formation, Mechanism

Zhe Li, Lei Liu. Recent advances in mechanistic studies on Ni catalyzed cross-coupling reactions[J]. Chinese Journal of Catalysis, 2015, 36(1): 3-14.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60217-5

https://www.cjcatal.com/EN/Y2015/V36/I1/3

References

[1] Corbet J P, Mignani G. Chem Rev, 2006, 106: 2651
[2] Magano J, Dunetz J R. Chem Rev, 2011, 111: 2177
[3] Cai S F, Wang D S, Niu Z Q, Li Y D. Chin J Catal (蔡双飞, 王定胜, 牛志强, 李亚栋. 催化学报), 2013, 34: 1964
[4] Torborg C, Beller M. Adv Synth Catal, 2009, 351: 3027
[5] Nicolaou K C, Bulger P G, Sarlah D. Angew Chem Int Ed, 2005, 44: 4442
[6] Wang Y F, Deng W, Liu L, Guo Q X. Chin J Org Chem (有机化学), 2005, 25: 8
[7] Li Z, Fu Y, Liu L, Guo Q X. Chin J Org Chem (有机化学), 2005, 25: 1508
[8] Rosen B M, Quasdorf K W, Wilson D A, Zhang N, Resmerita A M, Garg N K, Percec V. Chem Rev, 2011, 111: 1346
[9] Jana R, Pathak T P, Sigman M S. Chem Rev, 2011, 111: 1417
[10] Tasker S Z, Standley E A, Jamison T F. Nature, 2014, 509: 299
[11] Guan B T, Wang Y, Li B J, Yu D G, Shi Z J. J Am Chem Soc, 2008, 130: 14468
[12] Ke H H, Chen X F, Feng Y Y, Zou G. Sci China Chem, 2014, 57: 1126
[13] Li Z, Zhang S L, Fu Y, Guo Q X, Liu L. J Am Chem Soc, 2009, 131: 8815
[14] Zhou J, Fu G C. J Am Chem Soc, 2003, 125: 14726
[15] Zhou J, Fu G C. J Am Chem Soc, 2004, 126: 1340
[16] Powell D A, Fu G C. J Am Chem Soc, 2004, 126: 7788
[17] Csok Z, Vechorkin O, Harkins S B, Scopelliti R, Hu X L. J Am Chem Soc, 2008, 130: 8156
[18] Zhou Q, Srinivas H D, Dasgupta S, Watson M P. J Am Chem Soc, 2013, 135: 3307
[19] Harris M R, Hanna L E, Greene M A, Moore C E, Jarvo E R. J Am Chem Soc, 2013, 135: 3303
[20] Sylvester K T, Wu K, Doyle A G. J Am Chem Soc, 2012, 134: 16967
[21] Maity P, Shacklady-McAtee D M, Yap G P A, Sirianni E R, Watson M P. J Am Chem Soc, 2013, 135: 280
[22] Nielsen D K, Doyle A G. Angew Chem Int Ed, 2011, 50: 6056
[23] He A Y, Falck J R. J Am Chem Soc, 2010, 132: 2524
[24] Wang C, Ozaki T, Takita R, Uchiyama M. Chem Eur J, 2012, 18: 3482
[25] Oelke A J, Sun J W, Fu G C. J Am Chem Soc, 2012, 134: 2966
[26] Taylor B L H, Harris M R, Jarvo E R. Angew Chem Int Ed, 2012, 51: 7790
[27] Greene M A, Yonova I M, Williams F J, Jarvo E R. Org Lett, 2012, 14: 4293
[28] Taylor B L H, Swift E C, Waetzig J D, Jarvo E R. J Am Chem Soc, 2011, 133: 389
[29] Tamaru Y. Modern Organonickel Chemistry. Weinheim: Wiley-VCH, 2005
[30] Montgomery J. Angew Chem Int Ed, 2004, 43: 3890
[31] Tsou T T, Kochi J K. J Am Chem Soc, 1979, 101: 6319
[32] Lanni E L, McNeil A J. J Am Chem Soc, 2009, 131: 16573
[33] Liang T, Neumann C N, Ritter T. Angew Chem Int Ed, 2013, 52: 8214
[34] Lin B L, Liu L, Fu Y, Luo S W, Chen Q, Guo Q X. Organometallics, 2004, 23: 2114
[35] Breitenfeld J, Vechorkin O, Corminboeuf C, Scopelliti R, Hu X L. Organometallics, 2010, 29: 3686
[36] Jiang Y Y, Fu Y, Liu L. Sci China Chem, 2012, 55: 2057
[37] Li Z, Fu Y, Zhang S L, Guo Q X, Liu L. Chem Asian J, 2010, 5: 1475
[38] Li Z, Fu Y, Guo Q X, Liu L. Organometallics, 2008, 27: 4043
[39] Hartwig J F. Organotransition Metal Chemistry: From Bonding to Catalysis. New York: University Science Books, 2009
[40] Cornella J, Gómez-Bengoa E, Martin R. J Am Chem Soc, 2013, 135: 1997
[41] Zultanski S L, Fu G C. J Am Chem Soc, 2013, 135: 624
[42] Lin X F, Phillips D L. J Org Chem, 2008, 73: 3680
[43] Phapale V B, Guisan-Ceinos M, Bunuel E, Cardenas D J. Chem Eur J, 2009, 15: 12681
[44] Hu X L. Chem Sci, 2011, 2: 1867
[45] Jana R, Pathak T P, Sigman M S. Chem Rev, 2011, 111: 1417
[46] Saito B, Fu G C. J Am Chem Soc, 2007, 129: 9602
[47] Lu Z, Fu G C. Angew Chem Int Ed, 2010, 49: 6676
[48] Yi J, Liu J H, Liang J, Dai J J, Yang C T, Fu Y, Liu L. Adv Synth Catal, 2012, 354: 1685
[49] Li Z, Jiang Y Y, Fu Y. Chem Eur J, 2012, 18: 4345
[50] Tobisu M, Xu T, Shimasaki T, Chatani N. J Am Chem Soc, 2011, 133: 19505
[51] Lennox A J J, Lloyd-Jones G C. Angew Chem Int Ed, 2013, 52: 7362
[52] Liu L, Zhang S Y, Chen H, Lü Y, Zhu J, Zhao Y F. Chem Asian J, 2013, 8: 2592
[53] Gerber R, Frech C M. Chem Eur J, 2011, 17: 11893
[54] Tsou T T, Kochi J K. J Am Chem Soc, 1979, 101: 7547
[55] Morrell D G, Kochi J K. J Am Chem Soc, 1975, 97: 7262
[56] Dubinina G G, Brennessel W W, Miller J L, Vicic D A. Organometallics, 2008, 27: 3933
[57] Huang C Y, Doyle A G. J Am Chem Soc, 2012, 134: 9541
[58] Lin B L, Clough C R, Hillhouse G L. J Am Chem Soc, 2002, 124: 2890
[59] Ney J E, Wolfe J P. J Am Chem Soc, 2006, 128: 15415
[60] Sontag S K, Bilbrey J A, Huddleston N E, Sheppard G R, Allen W D, Locklin J. J Org Chem, 2014, 79: 1836
[61] Page M J, Lu W Y, Poulten R C, Carter E, Algarra A G, Kariuki B M, MacGregor S A, Mahon M F, Cavell K J, Murphy D M, Whittlesey M K. Chem Eur J, 2013, 19: 2158
[62] Breitenfeld J, Ruiz J, Wodrich M D, Hu X L. J Am Chem Soc, 2013, 135: 12004
[63] Zheng B, Tang F Z, Luo J, Schultz J W, Rath N P, Mirica L M. J Am Chem Soc, 2014, 136: 6499
[64] Harris M R, Konev M O, Jarvo E R. J Am Chem Soc, 2014, 136: 7825
[65] Gallego D, Brück A, Irran E, Meier F, Kaupp M, Driess M, Hartwig J F. J Am Chem Soc, 2013, 135: 15617
[66] Yi J, Lu X, Sun Y Y, Xiao B, Liu L. Angew Chem Int Ed, 2013, 52: 12409
[67] Amaike K, Muto K, Yamaguchi J, Itami K. J Am Chem Soc, 2012, 134: 13573
[68] Muto K, Yamaguchi J, Itami K. J Am Chem Soc, 2012, 134: 169
[69] Hong X, Liang Y, Houk K N. J Am Chem Soc, 2014, 136: 2017
[70] Lu Q Q, Yu H Z, Fu Y. J Am Chem Soc, 2014, 136: 8252
[71] Nakao Y, Takeda M, Matsumoto T, Hiyama T. Angew Chem Int Ed, 2010, 49: 4447
[72] Jiang Y Y, Li Z, Shi J. Organometallics, 2012, 31: 4356
[73] Biswas S, Weix D J. J Am Chem Soc, 2013, 135: 16192