镍催化偶联反应机理研究进展

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

催化学报 ›› 2015, Vol. 36 ›› Issue (1): 3-14.DOI: 10.1016/S1872-2067(14)60217-5

镍催化偶联反应机理研究进展

李哲, 刘磊

清华大学化学系, 北京100084

收稿日期:2014-08-11 修回日期:2014-09-04 出版日期:2014-12-31 发布日期:2014-12-31
通讯作者: 刘磊
基金资助:
国家高技术研究发展计划(863计划, 2012AA02A700); 国家自然科学基金(21221062).

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

Zhe Li, Lei Liu

Department of Chemistry, Tsinghua University, Beijing 100084, China

Received:2014-08-11 Revised:2014-09-04 Online:2014-12-31 Published:2014-12-31
Supported by:
This work was supported by the National High Technology Research and Development Program of China (863 Program, 2012AA02A700) and the National Natural Science Foundation of China (21221062).

摘要/Abstract

摘要：

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.

关键词: 镍, 均相催化, 偶联反应, C-C键形成, 反应机理

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

李哲, 刘磊. 镍催化偶联反应机理研究进展[J]. 催化学报, 2015, 36(1): 3-14.

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.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(14)60217-5

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

参考文献

[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

镍催化偶联反应机理研究进展

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

PDF

可视化

被引次数

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics

[1]	尹春, 杨甫林, 王书莉, 冯立纲. 异质结构NiSe₂/MoSe₂用于高效尿素辅助电解水制氢[J]. 催化学报, 2023, 51(8): 225-236.
[2]	陈宇卓, 王浩, 陆冰, 易倪, 曹亮, 王勇, 毛善俊. 用于高精度催化性能预测的精细结构敏感型深度学习框架[J]. 催化学报, 2023, 50(7): 284-296.
[3]	刘诗瑶, 巩玉同, 杨晓, 张楠楠, 刘会斌, 梁长海, 陈霄. 具有富电子镍位点的耐酸金属间化合物CaNi₂Si₂催化剂用于不饱和有机酸酐/酸的水相加氢[J]. 催化学报, 2023, 50(7): 260-272.
[4]	张功, 张炜松, 王小雨, 杨洋, 季定纬, 万伯顺, 陈庆安. 镍催化杂芳烃的非天然戊烯基化及环状单萜化反应[J]. 催化学报, 2023, 49(6): 123-131.
[5]	夏思源, 李奇远, 张仕楠, 许冬, 林秀, 孙露菡, 许景三, 陈接胜, 李国栋, 李新昊. Pd纳米立方体异质结尺寸依赖的电子界面效应对苯酚加氢反应的促进作用[J]. 催化学报, 2023, 49(6): 180-187.
[6]	李静静, 张锋伟, 詹新雨, 郭河芳, 张涵, 昝文艳, 孙振宇, 张献明. 酞菁镍分子结构的精确设计: 优化电子和空间效应用于CO₂电还原[J]. 催化学报, 2023, 48(5): 117-126.
[7]	刘丹卿, 张丙兴, 赵国强, 陈建, 潘洪革, 孙文平. 原位电化学扫描探针显微镜技术在电催化领域的应用进展[J]. 催化学报, 2023, 47(4): 93-120.
[8]	叶艳文, 胡一鸣, 郑万彬, 贾爱平, 王瑜, 鲁继青. 配体覆盖的Ir催化剂上巴豆醛加氢反应: 金属-有机物界面促进活性和选择性[J]. 催化学报, 2023, 47(4): 265-277.
[9]	刘润泽, 邵雪, 王畅, 戴卫理, 关乃佳. 甲醇制烃反应机理: 基础及应用研究[J]. 催化学报, 2023, 47(4): 67-92.
[10]	曾繁林, 朱虎林, 王茹楠, 袁晓亚, 孙凯, 屈凌波, 陈晓岚, 於兵. 一种用于光催化C(sp²)‒H键官能团化通用的非均相钒酸铋催化剂[J]. 催化学报, 2023, 46(3): 157-166.
[11]	Johannes A. Lercher. 三氧化钨催化糖分子选择裂解新机理及其对生物质利用的重要意义[J]. 催化学报, 2023, 46(3): 1-3.
[12]	黄志鹏, 杨阳, 穆骏驹, 李根恒, 韩建宇, 任濮宁, 张健, 罗能超, 韩克利, 王峰. 利用金属-自由基相互作用调控自由基的定向转化[J]. 催化学报, 2023, 45(2): 120-131.
[13]	谢起贤, 任丹, 柏力晨, 格日乐, 周雯慧, 白璐, 谢微, 王军虎, Michael Grätzel, 罗景山. 镍铁层状双金属氢氧化物在不同pH电解液体系中的析氧反应[J]. 催化学报, 2023, 44(1): 127-138.
[14]	孟翔宇, 李睿, 杨峻懿, 许世明, 张辰晨, 尤可嘉, 马宝春, 管红霞, 丁勇. 六核环状钴配合物用于光催化CO₂到CO转化[J]. 催化学报, 2022, 43(9): 2414-2424.
[15]	周紫璇, 高鹏. 多相催化CO₂加氢直接合成大宗化学品与液体燃料[J]. 催化学报, 2022, 43(8): 2045-2056.