Recent Advances in Cobalt Catalyzed Isocyanide Coupling Reactions

doi:10.6023/A18010023

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (5): 347-356.DOI: 10.6023/A18010023 Previous Articles Next Articles

Review

钴催化异腈参与的偶联反应研究进展

顾正洋, 纪顺俊

苏州大学材料与化学化工学部和纳米协同创新中心苏州 215123

投稿日期:2018-01-16 发布日期:2018-03-12
通讯作者: 纪顺俊,E-mail:shunjun@suda.edu.cn E-mail:shunjun@suda.edu.cn
作者简介:顾正洋,2013年本科毕业于苏州大学,2013年至今师从纪顺俊教授攻读理学博士学位.研究兴趣为过渡金属催化的异腈化学反应以及自由基化学反应等;纪顺俊,教授,有机化学专业博士生导师.1984年本科毕业于苏州大学并留校工作;1995年留学日本1997年进入博士课程并于2000年获得日本立教大学大学院理学博士学位,同年10月回苏州大学工作.主要开展应用有机合成反应和有机合成方法学(包括异腈、硫/硒、吲哚等多组分反应和有机杂环化合物的高效构筑、有机光电材料的合成及基础应用)等方面的研究工作.
基金资助:
感谢国家自然科学基金（Nos.21772137，21672157，21372174），江苏省高校自然科学基金重大基础研究项目（No.16KJA150002），江苏高校优势学科建设工程资助项目（PAPD），苏州大学国家和地方新型功能聚合材料联合工程实验室的支持.

Recent Advances in Cobalt Catalyzed Isocyanide Coupling Reactions

Gu Zhengyang, Ji Shunjun

College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China

Received:2018-01-16 Published:2018-03-12
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21772137, 21672157, 21372174), the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 16KJA150002), Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and Soochow University for financial support, and State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials.

Isocyanide is an important reactive reactant containing stable divalent carbon atoms, which has been widely used in the construction of nitrogen compounds, new drugs and natural products. During the past decades, exhaustive efforts have been devoted to the discovery of highly efficient reactions involving isocyanide on the basis of the development of the Passerini and Ugi reactions. Several types of reactions involving isocyanides have been reported, such as nucleophilic attack, electrophilic addition, imidoylation reactions, and oxidation, etc. Recently, isocyanides have found a new application as versatile C1 building blocks in transition metal catalysis. The transition metal catalyzed reactions involving isocyanide insertion offer a vast potential to construct C—C or C-N bonds for the synthesis of nitrogen-containing fine chemicals. As we know, the catalysts used in isocyanide insertion reactions are mainly concentrated in some valuable transition metals compounds, such as Pd, Rh, Ag and other metals. Therefore, the development of catalysts based on the naturally more abundant, cost efficient transition metal complexes, represents an attractive alternative. In this context, rather environmentally benign cobalt complexes bear great potential for applications in the coupling reactions. The reduced electronegativity of cobalt as compared to the homologous group 9 elements translates into more nucleophilic organometallic cobalt intermediates which allow for unprecedented reaction pathways in transition-metal catalyzed C—H activations as well as significantly improved positional and chemo-selectivities. And in the recent years, notable success has been achieved with the development of cobalt catalyzed C—H functionalizations with either in situ generated or single-component cobalt-complexes under mild reaction conditions. How to find and use the cost efficient cobalt-complexes to catalyze the isocyanide coupling reaction is of great significance. Our group has been devoted to explore the isocyanide chemistry, and in recent years, we have achieved several progresses in the reaction of cobalt-catalyzed isocyanides. In this review we summarize the recent advances in the cobalt-catalyzed isocyanide coupling reactions.

Key words: isocyanide, nitrogen-containing chemicals, Co-catalysis, coupling reaction, free radical reaction

Cite this article

Gu Zhengyang, Ji Shunjun. Recent Advances in Cobalt Catalyzed Isocyanide Coupling Reactions[J]. Acta Chim. Sinica, 2018, 76(5): 347-356.

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References

[1] Lieke, W. Ann. Chem. Pharm. 1859, 112, 316.
[2] Scheuer, P. J. Acc. Chem. Res. 1992, 25, 433.
[3] Passerini, M. Gazz. Chim. Ital. 1921, 51, 126.
[4] Ugi, I.; Mey, R.; Fetzer, U.; Steinbruckner, C. Angew. Chem. 1959, 71, 386.
[5] Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661.
[6] Recent development of the Passerini and Ugi reactions, see selected reviews:
(a) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168;
(b) Zhu, J. Eur. J. Org. Chem. 2003, 1133;
(c) Dömling, A. Chem. Rev. 2006, 106, 17;
(d) Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234.
(e) Sadjadi, S.; Heravi, M. M. Tetrahedron 2011, 67, 2707;
(f) Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083.
[7] (a) Liao, J.-Y.; Shao, P.-L.; Zhao, Y. J. Am. Chem. Soc. 2015, 137, 628.
(b) Kobiki, Y.; Kawaguchi, S.; Ogawa, A. Org. Lett. 2015, 17, 3490.
(c) Zhang, Z.; Li, Z.-Y.; Fu, B.; Zhang, Z.-H. Chem. Commun. 2015, 51, 16312.
(d) Zhang, Z.; Huang, B.-L.; Qiao, G.-Y.; Zhu, L.; Xiao, F.; Chen, F.; Fu, B.; Zhang, Z.-H. Angew. Chem. Int. Ed. 2017, 56, 1.
[8] (a) Saluste, C. G.; Whitby, R. J.; Furber, M. Angew. Chem. Int. Ed. 2000, 39, 4156;
(b) Saluste, C. G.; Whitby, R. J.; Furber, M. Tetrahedron Lett. 2001, 42, 6191;
(c) Tetala, K. K. R.; Whitby, R. J.; Light, M. E.; Hurtshouse, M. B. Tetrahedron Lett. 2004, 45, 6991;
(d) Saluste, C. G.; Crumpler, S.; Furber, M.; Whitby, R. J. Tetrahedron Lett. 2004, 45, 6995.
(e) Whitby, R. J.; Saluste, C. G.; Furber, M. Org. Biomol. Chem. 2004, 2, 1974.
[9] (a) Baelen, G. V.; Kuijer, S.; Rýcek, L.; Sergeyev, S.; Janssen, E.; de Kanter, F. J. J.; Maes, B. U. W.; Ruijter, E.; Orru, R. V. A. Chem. Eur. J. 2011, 17, 15039;
(b) Estévez, V.; Baelen, G. V.; Lentferink, B. H.; Vlaar, T.; Janssen, E.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. ACS Catal. 2014, 4, 40;
(c) Vlaar, T.; Ruijter, E.; Znabet, A.; Janssen, E.; de Kanter, F. J. J.; Maes, B. U. W.; Orru, R. V. A. Org. Lett. 2011, 13, 6496.
[10] (a) Jaing, H.-F.; Liu, B.-F.; Li, Y.-B.; Wang, A.-Z.; Huang, H.-W. Org. Lett. 2011, 13, 1028;
(b) Li, Y.-B.; Zhao, J.; Chen, H.-J.; Liu, B.; Jiang, H.-F. Chem. Commun. 2012, 48, 3545;
(c) Liu, B.-F.; Li, Y.-B.; Yin, M.-Z.; Wu, W.-Q.; Jiang, H.-F. Chem. Commun. 2012, 48, 11446;
(d) Jaing, H.-F.; Yin, M.-Z.; Li, Y.-B.; Liu, B.-F.; Zhao, J.-S.-W.; Wu, W.-Q. Chem. Commun. 2014, 50, 2037;
(e) Liu, B.-F.; Li, Y.-B.; Jaing, H.-F.; Yin, M.-Z.; Huang, H.-W. Adv. Synth. Catal. 2012, 354, 2288.
(f) Li, Z.; Zheng, J.; Hu, W.-G.; Li, J.-X.; Wu, W.-Q.; Jaing, H.-F. Org. Chem. Front. 2017, 4, 1363.
[11] (a) Qiu, G.; Liu, G.; Pu, S.-Z.; Wu, J. Chem. Commun. 2012, 48, 2903;
(b) Qiu, G.; He, Y.-H.; Wu, J. Chem. Commun. 2012, 48, 3836;
(c) Qiu, G.; Liu, Y.; Wu, J. Org. Biomol. Chem. 2013, 11, 798.
[12] (a) Wang, J.; Luo, S.; Huang, J.-B.; Mao, T.-T.; Zhu, Q. Chem. Eur. J. 2014, 20, 11220;
(b) Li, J.; He, Y.-M.; Luo, S.; Lei, J.; Wang, J.; Xie, Z.-Q.; Zhu, Q. J. Org. Chem. 2015, 80, 2223.
[13] (a) Huang, X.-S.; Cong, X.-F.; Mi, P.-B.; Bi, X.-H. Chem. Commun. 2017, 53, 3858.
(b) Fang, G.-C.; Liu, J.-Q.; Fu, J.-K.; Liu, Q.; Bi, X.-H. Org. Lett. 2017, 19, 1346.
(c) Wang, Y.-M.; KiranKumar, R.; Bi, X.-H. Tetrahedron Lett. 2016, 57, 5730.
(d) Xiao, P.; Yuan, H.-Y.; Liu, J.-Q.; Zheng, Y.-Y.; Bi, X.-H.; Zhang, J.-P. ACS Catal. 2015, 5, 6177.
[14] (a) Ren, S.-B.; Zhang, H.-F.; Zhang, J.; Zhang, W.; Liu, Y.-K. Chin. J. Org. Chem. 2016, 36, 1954(in Chinese). (任少波, 张海峰, 张剑, 张巍, 刘运奎, 有机化学, 2016, 36, 1954)
(b) Sun, X.-Y.; Wang, W.-M.; Ma, J.; Yu, S.-Y. Acta Chim. Sinica 2017, 75, 115(in Chinese). (孙晓阳, 王文敏, 马晶, 俞寿云, 化学学报, 2017, 75, 115).
[15] (a) Vllar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem. Int. Ed. 2013, 52, 7084;
(b) Qiu, G.; Ding, Q.-P.; Wu, J. Chem. Soc. Rev. 2013, 42, 5257.
[16] Kharasch, M. S.; Fields, E. K. J. Am. Chem. Soc. 1941, 63, 2316.
[17] Hebrard, F.; Kalck, P. Chem. Rev. 2009, 109, 4272.
[18] (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc. D 1971, 36a.
(b) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Perkin Trans. 1 1973, 975.
[19] Sugano, K.; Tanase, T.; Kobayashi, K.; Yamamoto, Y. Chem. Lett. 1991, 921.
[20] Zhu, T.-H.; Wang, S.-Y.; Wang, G.-N.; Ji, S.-J. Chem. Eur. J. 2013, 19, 5850.
[21] Zhu, T.-H.; Xu, X.-P.; Cao, J.-J.; Wei, T.-Q.; Wang, S.-Y.; Ji, S.-J. Adv. Synth. Catal. 2014, 356, 509.
[22] Zhu, T.-H.; Wang, S.-Y.; Wei, T.-Q.; Ji, S.-J. Adv. Synth. Catal. 2015, 357, 823.
[23] Zhu, T.-H.; Wang, S.-Y.; Tao, Y.-Q.; Wei, T.-Q.; Ji, S.-J. Org. Lett. 2014, 16, 1260.
[24] Xu, P.; Zhu, T.-H.; Wei, T.-Q.; Wang, S.-Y.; Ji, S.-J. RSC Adv. 2016, 6, 32467.
[25] Ahmadi, F.; Bazgir, A. RSC Adv. 2016, 6, 61955.
[26] Gao, Q.; Zhou, P.; Liu, F.; Hao, W.-J.; Yao, C.; Jiang, B.; Tu, S.-J. Chem. Commun. 2015, 51, 9519.
[27] Gu, Z.-Y.; Liu, C.-G.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2017, 82, 2223.
[28] Zou, F.-H.; Chen, X.-W.; Hao, W.-Y. Tetrahedron 2017, 73, 758.
[29] Kalsi, D.; Barsu, N.; Sundararaju, B. Chem. Eur. J. 2018, 24, 1.
[30] (a) Cui, X.; Xu, X.; Jin, L.-M.; Wojtas, L.; Zhang, X. P. Chem. Sci. 2015, 6, 1219.
(b) Zhu, S.-F.; Xu, X.; Perman, J. A.; Zhang, X. P. J. Am. Chem. Soc. 2010, 132, 12796.
(c) Xu, X.; Lu, H.-J.; Ruppel, J. V.; Cui, X.; de Mesa, S. L.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 15292.
[31] (a) Goswami, M.; Lyaskovskyy, V.; Domingos, S. R.; Buma, W. J.; Woutersen, S.; Troeppner, O.; Ivanovic-Burmazovic, I.; Lu, H.-J.; Cui, X.; Zhang, X. P.; Reijerse, E. J.; DeBeer, S.; van Schooneveld, M. M.; Pfaff, F. F.; Ray, K.; de Bruin, B. J. Am. Chem. Soc. 2015, 137, 5468.
(b) Paul, N. D.; Mandal, S.; Otte, M.; Cui, X.; Zhang, X. P.; de Bruin, B. J. Am. Chem. Soc. 2014, 136, 1090.
[32] Gu, Z.-Y.; Liu, Y.; Wang, F.; Bao, X.-G.; Wang, S.-Y.; Ji, S.-J. ACS Catal. 2017, 7, 3893.
[33] Jiang, T.; Gu, Z.-Y.; Yin, L.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2017, 82, 7913.
[34] Gu, Z.-Y.; Li, J.-H.; Wang, S.-Y.; Ji, S.-J. Chem. Commun. 2017, 53, 11173.

钴催化异腈参与的偶联反应研究进展

Recent Advances in Cobalt Catalyzed Isocyanide Coupling Reactions

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