氮杂环卡宾催化有机反应的研究进展

doi:10.6023/cjoc201702041

有机化学 ›› 2017, Vol. 37 ›› Issue (10): 2590-2608.DOI: 10.6023/cjoc201702041 上一篇下一篇

综述与进展

氮杂环卡宾催化有机反应的研究进展

王翱^a,b, 肖永龙^b, 周宇^b, 徐进宜^a, 柳红^b

a 中国药科大学天然药物活性物质与功能国家重点实验室南京 210000;
b 中国科学院上海药物研究所受体结构与功能重点实验室上海 201203

收稿日期:2017-02-26 修回日期:2017-05-25 发布日期:2017-06-02
通讯作者: 周宇, 柳红 E-mail:zhouyu@simm.ac.cn;hliu@simm.ac.cn
基金资助:
国家自然科学基金（No.21632008）资助项目.

Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes

Wang Ao^a,b, Xiao Yonglong^b, Zhou Yu^b, Xu Jinyi^a, Liu Hong^b

a State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210000;
b CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received:2017-02-26 Revised:2017-05-25 Published:2017-06-02
Contact: 10.6023/cjoc201702041 E-mail:zhouyu@simm.ac.cn;hliu@simm.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No.21632008).

文章分享

摘要/Abstract

自从1991年Arduengo第一次分离得到稳定的游离N-杂环卡宾以来，其作为一种高效的有机催化剂得到了迅速的发展.由于N-杂环卡宾的极性反转特性，它在有机合成中构建复杂分子的地位举足轻重.一些特定的路易斯碱及氧化剂可诱导卡宾与羰基化合物形成Breslow中间体、烯醇化合物和高烯醇化合物，这些中间体极大地拓展了卡宾的应用范围.综述了近几年N-杂环卡宾在催化有机反应中的研究进展，如催化安息香缩合反应、Stetter反应、a³-d³极性反转反应、环合反应和氟化反应等.

关键词: 氮杂环卡宾, 有机催化剂, 极性反转

Since the first stable N-heterocyclic carbene was isolated by Arduengo in 1991, N-heterocyclic carbine has developed rapidly as a kind of efficient organic catalyst. It plays important role in building complex molecules in organic synthesis for the characteristics of umpolung. Some special Lewis bases and oxidants can induce carbine reaction with carbonyl to form Breslow intermediates, enol and homoenolate, which expand the reaction greatly. In this paper, the recent progresses in organic catalytic reactions including Stetter reaction, a³-d³ umpolung catalyzed by carbines are reviewed.

Key words: N-heterocyclic carbene, organic catalytic, umpolung

引用此文

王翱, 肖永龙, 周宇, 徐进宜, 柳红. 氮杂环卡宾催化有机反应的研究进展[J]. 有机化学, 2017, 37(10): 2590-2608.

Wang Ao, Xiao Yonglong, Zhou Yu, Xu Jinyi, Liu Hong. Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes[J]. Chin. J. Org. Chem., 2017, 37(10): 2590-2608.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Nef, J. U. Justus Liebigs Ann. Chem. 1895, 287, 265.
[2] Lin, J. C. Y.; Huang, R. T. W.; Lee, C. S.; Bhattacharyya, A.; Hwang, W. S.; Lin, I. J. B. Chem. Rev. 2009, 109, 3561.
[3] Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978.
[4] Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239.
[5] Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 296.
[6] Shapiro, L. R.; Samuels, S.; Breslow, L.; Camacho, T. Am. J. Public Health 1983, 73, 773.
[7] Enders, D.; Grossmann, A.; Fronert, J.; Raabe, G. Chem. Commun. 2010, 46, 6282.
[8] Thai, K.; Langdon, S. M.; Bilodeau, F.; Gravel, M. Org. Lett. 2013, 15, 2214.
[9] Langdon, S. M.; Wilde, M. M.; Thai, K.; Gravel, M. J. Am. Chem. Soc. 2014, 136, 7539.
[10] Haghshenas, P.; Gravel, M. Org. Lett. 2016, 18, 4518.
[11] Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696.
[12] DiRocco, D. A.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 5904.
[13] Sun, L. H.; Liang, Z. Q.; Jia, W. Q.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 5803.
[14] Xu, J.; Mou, C.; Zhu, T.; Song, B. A.; Chi, Y. R. Org. Lett. 2014, 16, 3272.
[15] Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15.
[16] Ciganek, E. Synthesis-Stuttgart 1995, 1311.
[17] Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021.
[18] de Alaniz, J. R.; Kerr, M. S.; Moore, J. L.; Rovis, T. J. Org. Chem. 2008, 73, 2033.
[19] Cullen, S. C.; Rovis, T. Org. Lett. 2008, 10, 3141.
[20] Wang, Z.; Yu, Z.; Wang, Y.; Shi, D. Synthesis 2012, 44, 1559.
[21] Law, K. R.; McErlean, C. S. P. Chem.-Eur. J. 2013, 19, 15852.
[22] Liu, G.; Wilkerson, P. D.; Toth, C. A.; Xu, H. Org. Lett. 2012, 14, 858.
[23] Li, Y.; Shi, F.-Q.; He, Q.-L.; You, S.-L. Org. Lett. 2009, 11, 3182.
[24] Vedachalam, S.; Tan, S. M.; Teo, H. P.; Cai, S.; Liu, X.-W. Org. Lett. 2012, 14, 174.
[25] Bortolini, O.; Fantin, G.; Fogagnolo, M.; Giovannini, P. P.; Massi, A.; Pacifico, S. Org. Biomol. Chem. 2011, 9, 8437.
[26] Zhang, J.; Xing, C.; Tiwari, B.; Chi, Y. R. J. Am. Chem. Soc. 2013, 135, 8113.
[27] Fang, X.; Chen, X.; Chi, Y. R. Org. Lett. 2011, 13, 4708.
[28] McCusker, E. O.; Scheidt, K. A. Angew. Chem., Int. Ed. 2013, 52, 13616.
[29] Xu, J.; Chen, X.; Wang, M.; Zheng, P.; Song, B. A.; Chi, Y. R. Angew. Chem., Int. Ed. 2015, 54, 5161.
[30] Zhao, X.; Ruhl, K. E.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 12330.
[31] Mo, J.; Yang, R.; Chen, X.; Tiwari, B.; Chi, Y. R. Org. Lett. 2013, 15, 50.
[32] Li, F.; Wu, Z.; Wang, J. Angew. Chem., Int. Ed. 2015, 54, 656.
[33] Xu, J.; Yuan, S.; Peng, J.; Miao, M.; Chen, Z.; Ren, H. Chem. Commun. 2017, 53, 3430.
[34] Zhang, H.-M.; Gao, Z.-H.; Ye, S. Org. Lett. 2014, 16, 3079.
[35] Zhao, Y. M.; Cheung, M. S.; Lin, Z.; Sun, J. Angew. Chem., Int. Ed. 2012, 51, 10359.
[36] Ni, Q.; Zhang, H.; Grossmann, A.; Loh, C. C.; Merkens, C.; Enders, D. Angew. Chem., Int. Ed. 2013, 52, 13562.
[37] Dong, X.; Yang, W.; Hu, W.; Sun, J. Angew. Chem., Int. Ed. 2015, 54, 660.
[38] Rong, Z. Q.; Jia, M. Q.; You, S. L. Org. Lett. 2011, 13, 4080.
[39] Yao, C.; Wang, D.; Lu, J.; Li, T.; Jiao, W.; Yu, C. Chemistry 2012, 18, 1914.
[40] Leong, W. W. Y.; Chen, X.; Chi, Y. R. Green Chem. 2013, 15, 1505.
[41] Raup, D. E.; Cardinal-David, B.; Holte, D.; Scheidt, K. A. Nat. Chem. 2010, 2, 766.
[42] Zhao, X.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 12466.
[43] De Vreese, R.; D'Hooghe, M. Beilstein J. Org. Chem. 2012, 8, 398.
[44] Chen, X.; Fang, X.; Chi, Y. R. Chem. Sci. 2013, 4, 2613.
[45] Nair, V.; Sinu, C. R.; Babu, B. P.; Varghese, V.; Jose, A.; Suresh, E. Org. Lett. 2009, 11, 5570.
[46] Maji, B.; Ji, L.; Wang, S.; Vedachalam, S.; Ganguly, R.; Liu, X. W. Angew. Chem., Int. Ed. 2012, 51, 8276.
[47] White, N. A.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 8504.
[48] Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8592.
[49] Zhang, Z.; Zeng, X.; Xie, D.; Chen, D.; Ding, L.; Wang, A.; Yang, L.; Zhong, G. Org. Lett. 2015, 17, 5052.
[50] Xia, W.; Yao, H.; Liu, D.; Zhao, L.; Zhou, Y.; Liu, H. Adv. Synth. Catal. 2016, 358, 1864.
[51] Lv, H.; Tiwari, B.; Mo, J.; Xing, C.; Chi, Y. R. Org. Lett. 2012, 14, 5412.
[52] Jiang, K.; Tiwari, B.; Chi, Y. R. Org. Lett. 2012, 14, 2382.
[53] Chen, X. Y.; Xia, F.; Cheng, J. T.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 10644.
[54] Mo, J.; Shen, L.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8588.
[55] Fu, Z.; Xu, J.; Zhu, T.; Leong, W. W.; Chi, Y. R. Nat. Chem. 2013, 5, 835.
[56] Xie, Y.; Yu, C.; Li, T.; Tu, S.; Yao, C. Chemistry 2015, 21, 5355.
[57] Shen, L.-T.; Shao, P.-L.; Ye, S. Adv. Synth. Catal. 2011, 353, 1943.
[58] Que, Y.; Li, T.; Yu, C.; Wang, X. S.; Yao, C. J. Org. Chem. 2015, 80, 3289.
[59] Rong, X.; Yao, H.; Xia, W.; Du, Y.; Zhou, Y.; Liu, H. ACS Comb. Sci. 2016, 18, 220.
[60] Mo, J.; Chen, X.; Chi, Y. R. J. Am. Chem. Soc. 2012, 134, 8810.
[61] Wang, M.; Huang, Z.; Xu, J.; Chi, Y. R. J. Am. Chem. Soc. 2014, 136, 1214.
[62] Liang, Z.-Q.; Wang, D.-L.; Zhang, H.-M.; Ye, S. Org. Lett. 2015, 17, 5140.
[63] Xu, J.; Yuan, S.; Miao, M. Org. Lett. 2016, 18, 3822.
[64] Xiao, Y.; Wang, J.; Xia, W.; Shu, S.; Jiao, S.; Zhou, Y.; Liu, H. Org. Lett. 2015, 17, 3850.
[65] Chen, X.; Yang, S.; Song, B. A.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 11134.
[66] Zhu, T.; Mou, C.; Li, B.; Smetankova, M.; Song, B. A.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 5658.
[67] Pellissier, H. Tetrahedron 2008, 64, 1563.
[68] Lu, S.; Poh, S. B.; Siau, W. Y.; Zhao, Y. Angew. Chem., Int. Ed. 2013, 52, 1731.
[69] Telfer, S. Coord. Chem. Rev. 2003, 242, 33.
[70] Lu, S.; Poh, S. B.; Zhao, Y. Angew. Chem., Int. Ed. 2014, 53, 11041.
[71] Steinreiber, J.; Faber, K.; Griengl, H. Chemistry 2008, 14, 8060.
[72] Cohen, D. T.; Eichman, C. C.; Phillips, E. M.; Zarefsky, E. R.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 7309.
[73] Goodman, C. G.; Johnson, J. S. J. Am. Chem. Soc. 2014, 136, 14698.
[74] Goodman, C. G.; Walker, M. M.; Johnson, J. S. J. Am. Chem. Soc. 2015, 137, 122.
[75] Wu, Z.; Li, F.; Wang, J. Angew. Chem., Int. Ed. 2015, 54, 1629.
[76] Babu, R. S.; O'Doherty, G. A. J. Am. Chem. Soc. 2003, 125, 12406.
[77] Sugawara, K.; Imanishi, Y.; Hashiyama, T. Tetrahe-dron-Asymmetry 2000, 11, 4529.
[78] Chen, X.; Fong, J. Z.; Xu, J.; Mou, C.; Lu, Y.; Yang, S.; Song, B. A.; Chi, Y. R. J. Am. Chem. Soc. 2016, 138, 7212.
[79] White, N. A.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 14674.
[80] Zhang, Y.; Du, Y.; Huang, Z.; Xu, J.; Wu, X.; Wang, Y.; Wang, M.; Yang, S.; Webster, R. D.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 2416.
[81] Li, B.-S.; Wang, Y.; Proctor, R. S. J.; Zhang, Y.; Webster, R. D.; Yang, S.; Song, B.; Chi, Y. R. Nat. Commun. 2016, 7.
[82] Reddi, R. N.; Prasad, P. K.; Sudalai, A. Angew. Chem., Int. Ed. 2015, 54, 14150.
[83] Nakano, Y.; Lupton, D. W. Angew. Chem., Int. Ed. 2016, 55, 3135.
[84] Patra, A.; Mukherjee, S.; Das, T. K.; Jain, S.; Gonnade, R. G.; Biju, A. T. Angew. Chem., Int. Ed. 2017, 56, 2730.
[85] Ungureanu, A.; Levens, A.; Candish, L.; Lupton, D. W. Angew. Chem., Int. Ed. 2015, 54, 11780.

氮杂环卡宾催化有机反应的研究进展

Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes

PDF

可视化

被引次数

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 15

编辑推荐

相关统计

本文评价

[1]	夏登鹏, 罗锦昀, 何林, 蔡志华, 杜广芬. 氮杂环卡宾催化的五氟苯基硫醚的合成[J]. 有机化学, 2024, 44(2): 622-630.
[2]	杨爽, 房新强. 氮杂环卡宾催化实现的动力学拆分近期研究进展[J]. 有机化学, 2024, 44(2): 448-480.
[3]	蔡远林, 吕亚, 聂桂花, 金智超, 池永贵. 氮杂环卡宾催化合成氰基化合物的研究进展[J]. 有机化学, 2023, 43(9): 3135-3145.
[4]	杨亮茹, 郭梦丽, 袁金伟, 王佳美, 夏宇婷, 肖咏梅, 毛璞. 钳形氮杂环卡宾金属络合物的研究进展[J]. 有机化学, 2023, 43(6): 2002-2025.
[5]	戴春波, 夏思奇, 陈晓玉, 杨丽敏. 氮杂环卡宾(NHC)催化[4+3]环加成反应构建4-氨基苯并环庚烯内酯[J]. 有机化学, 2023, 43(3): 1084-1090.
[6]	刘婷婷, 胡宇才, 沈安. 亚胺配体协同氮杂环卡宾钯配合物催化碳碳偶联反应的作用机制[J]. 有机化学, 2023, 43(2): 622-628.
[7]	赵薇, 刘京, 何向奎, 蒋豪, 陆良秋, 肖文精. 氮杂环卡宾(NHC)催化的联芳基二醛去对称化构建轴手性醛类化合物[J]. 有机化学, 2022, 42(8): 2504-2514.
[8]	姚婷, 李佳燕, 王佳明, 赵常贵. 氮杂环卡宾催化构筑含七元环结构的研究进展[J]. 有机化学, 2022, 42(4): 925-944.
[9]	高珠鹏, 项锴, 徐学涛, 张雅婷, 朱道勇. 环状三价碘试剂参与的β-二羰基化合物的α-苯甲酰氧基化反应[J]. 有机化学, 2022, 42(11): 3766-3775.
[10]	孟祥辉, 杨亮茹, 刘琪琳, 董振华, 袁金伟, 肖咏梅, 毛璞. 酰胺功能化吡啶/嘧啶螯合氮杂环卡宾钯化合物的合成、结构及其催化的咪唑C-5芳基化反应[J]. 有机化学, 2022, 42(11): 3747-3756.
[11]	成立, 王文蓉, 孙玉倩, 李团结, 于晨侠, 姚昌盛. 氮杂环卡宾(NHC)/银(I)共催化合成2-氧代-2-芳乙基芳甲酸酯[J]. 有机化学, 2021, 41(4): 1607-1613.
[12]	张雨霞, 郭京程, 黄杰, 付振乾. 氮杂环卡宾催化乙酸酯和β-硅基烯酮的[4+2]环合反应:高立体选择性合成β-硅基δ-内酯[J]. 有机化学, 2021, 41(11): 4467-4475.
[13]	张建明, 高健, 冯捷, 陆涛, 杜鼎. 氮杂环卡宾/过渡金属联合催化研究进展[J]. 有机化学, 2021, 41(10): 3792-3807.
[14]	张永娜, 段慧欣, 汪游清. 手性伯胺作为有机催化剂对亚胺的不对称反应研究进展[J]. 有机化学, 2020, 40(6): 1514-1528.
[15]	张阳, 邢芬, 冯泽男, 杜广芬, 顾承志, 何林. 氮杂环卡宾催化氰基乙酸酯与二烯酮双Michael反应:非对映选择性合成多取代环己酮和茚[J]. 有机化学, 2020, 40(6): 1608-1617.