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近期发展了很多镍催化的偶联反应作为在有机合成中高效构建C–C键的方法,同时开展了很多关于控制镍催化反应活性和选择性的机理研究。这些研究发现,镍催化反应机理往往和相应的钯催化反应机理不同,因为镍催化偶联经常包括自由基和双金属机理。本文总结了镍催化偶联反应机理的最新进展。对于这些反应机理的理解为发展具有更高效率和选择性的镍催化偶联反应提供了帮助。

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 im‐proved efficiency and selectivity.

参考文献

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