胺-胺氧化偶联合成亚胺的研究进展

doi:10.6023/cjoc201801017

有机化学 ›› 2018, Vol. 38 ›› Issue (6): 1350-1363.DOI: 10.6023/cjoc201801017 上一篇下一篇

综述与进展

胺-胺氧化偶联合成亚胺的研究进展

刘迪, 张成慧, 韩楠, 杜萌萌, 张效露, 赵朋杉, 杨萍

山东科技大学化学与环境工程学院青岛 266590

收稿日期:2018-01-09 修回日期:2018-02-09 发布日期:2018-02-11
通讯作者: 刘迪,E-mail:ld002037132@163.com E-mail:ld002037132@163.com
基金资助:
海藻活性物质国家重点实验室开放基金（No.SKL-BASS1723）资助项目.

Progress in Oxidative Coupling of Amines to Imines

Liu Di, Zhang Chenghui, Han Nan, Du Mengmeng, Zhang Xiaolu, Zhao Pengshan, Yang Ping

College of Chemical and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590

Received:2018-01-09 Revised:2018-02-09 Published:2018-02-11
Contact: 10.6023/cjoc201801017 E-mail:ld002037132@163.com
Supported by:
Project supported by the Open Foundation of the State Key Laboratory of Bioactive Seaweed Substances (No. SKL-BASS1723).

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摘要/Abstract

亚胺是一类性质活泼的中间体且具有很好的抗菌作用，因而受到广泛关注.胺-胺氧化偶联合成亚胺的路线由于具有原子经济性高和对环境友好等优点，已成为研究的热点.主要从催化剂及其催化机理两方面对胺-胺氧化偶联合成亚胺的研究进展进行综述.分别对贵金属、非贵金属、光催化、仿生催化以及聚苯胺、氧化石墨、偶氮二异丁腈等体系催化的胺-胺氧化偶联合成亚胺反应进行了详细地介绍，重点论述了各种催化剂的催化性能、优缺点和底物适用范围，还对主要催化体系的催化机理作了分析.需要指出，尽管目前胺-胺氧化偶联合成亚胺的催化剂研究已有了较大的发展，但在一定程度上依然存在着催化剂成本高，反应条件苛刻，对胺-胺交叉氧化偶联反应的催化性能较低，以及需要使用特定氧化剂、碱性助剂和溶剂等缺点.最后，基于胺-胺氧化偶联合成亚胺路线存在的问题，指出了该领域的研究方向.

关键词: 胺, 氧化偶联, 亚胺, 过渡金属催化, 光催化, 仿生催化

Imines are a class of active intermediates and have good antibacterial activity, therefore, they have received the extensive concern of scientists. Since the preparation method of imines by oxidative coupling of amines has the advantages of high atom economy and environmental friendliness, it has become a research hotspot. The recent progress in oxidative coupling of amines to imines is summarized from two aspects:catalyst and catalytic mechanism in this article. We introduced all kinds of catalytic systems in detail such as noble metal, non-noble metal, photocatalysis, biomimetic catalysis, poly aniline, graphite oxide, and azobisisobutyronitrile (AIBN). The catalytic performance, advantages and drawbacks and applicability of which are highlighted. And the catalytic mechanisms of the main catalytic systems are also discussed. It should be pointed out that these catalytic systems for oxidative coupling of amines to imines showed varying degrees of success as well as limitations like high cost of catalyst, harsh reaction condition, use of oxidant, alkaline additives and/or toxic organic solvents. Finally, based on the existential problems for oxidative coupling of amines to imines, the research directions in this field are predicted.

Key words: amines, oxidation coupling, imines, transition-metal catalysis, photocatalysis, biomimetic catalysis

引用此文

刘迪, 张成慧, 韩楠, 杜萌萌, 张效露, 赵朋杉, 杨萍. 胺-胺氧化偶联合成亚胺的研究进展[J]. 有机化学, 2018, 38(6): 1350-1363.

Liu Di, Zhang Chenghui, Han Nan, Du Mengmeng, Zhang Xiaolu, Zhao Pengshan, Yang Ping. Progress in Oxidative Coupling of Amines to Imines[J]. Chin. J. Org. Chem., 2018, 38(6): 1350-1363.

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参考文献

[1] Kobayashi, S.; Mori, Y.; Fossey, J.-S.; Salter, M.-M. Chem.Rev. 2011, 111, 2626.
[2] Adams, J.-P. J.Chem. Soc., Perkin Trans.1 2000, 125.
[3] Ashok, M.; Holla, B.-S.; Poojary, B. Eur.J.Med.Chem. 2007, 46, 1095.
[4] Young, J.-N.; Chang, T.-C.; Tsai, S.-C.; Yang, L.; Yu, S.-C. J.Catal. 2010, 272, 253.
[5] Santos, L.-L.; Serna, P.; Corma, A. Chem.-Eur.J. 2009, 15, 8196.
[6] Zanardi, A.; Mata, J.-A.; Peris, E. Chem.-Eur.J. 2010, 16, 10502.
[7] Maggi, A.; Madsen, R. Organometallics 2012, 31, 451.
[8] Kwon, M.-S.; Kim, S.; Park, S.; BoscoO, W.; Chidrala, R.-K.; Park, J. J.Org.Chem. 2009, 74, 2877.
[9] Jiang, G.; Chen, J.; Huang, J.-S.; Che, C.-M. Org.Lett. 2009, 11, 4568.
[10] Bailey, A.-J.; James, B.-R. Chem.Commun. 1996, 0, 2343.
[11] Prades, A.; Peris, E.; Albrecht, M. Organometallics 2011, 30, 1162.
[12] Doctorovich, F.; Granara, M.; Salvo, F.-D. Transition Met. Chem. 2001, 26, 505.
[13] He, L.-P.; Chen, T.; Gong, D.; Lai, Z.; Huang, K.-W. Organometallics 2012, 31, 5208.
[14] Zhang, Y.-C.; Lu, F.; Huang, R.; Zhang, H.-Y.; Zhao, J.-Q. Catal.Commun. 2016, 81, 10.
[15] Zhu, B.; Angelici, R.-J. Chem.Commun. 2007, 38, 2157.
[16] Zhu, B.; Lazar, M.; Trewyn, B.-G.; Angelici, R.-J. J.Catal. 2008, 260, 1.
[17] Grirrane, A.; Corma, A.; Garcia, H. J.Catal. 2009, 264, 138.
[18] Perez, Y.; Aprile, C.; Corma, A.; Garcia, H. Catal Lett. 2010, 134, 204.
[19] Ishida, T.; Kawakita, N.; Akita, T.; Haruta, M. Gold Bull. 2009, 42, 267.
[20] Srimani, D.; Feller, M.; Ben-David, Y.; Milstein, D. Chem.Commun. 2012, 48, 11853.
[21] Lu, S.-L.; Wang, J. Q.; Cao, X. Q.; Li, X. M.; Gu, H. W. Chem. Commun. 2014, 50, 3512.
[22] Patil, R.-D.; Adimurthy, S. Adv.Synth. Catal. 2011, 353, 1695.
[23] Patil, R.-D, Adimurthy, S. RSC Adv. 2012, 2, 5119.
[24] Patil, R.-D, Adimurthy, S. Asian J.Org. Chem. 2013, 2, 726.
[25] Hu, Z.-Z.; Kerton, F.-M. Org.Biomol.Chem. 2012, 10, 1618.
[26] Huang, B.; Tian, H.; Lin, S.; Xie, M.; Yu, X.; Xu, Q. Tetrahedron Lett. 2013, 54, 2861.
[27] Largeron, M.; Fleury, M.-B. Chem.-Eur. J. 2015, 21, 1.
[28] Wang, J.; Lu, S.; Cao, X.; Gu, H. Chem.Commun. 2014, 50, 5637.
[29] Al-Hmoud, L.; Jones, C.-W. J.Catal. 2013, 301, 116.
[30] Marui, K.; Nomoto, A.; Ueshima, M.; Ogawa, A. Tetrahedron Lett. 2015, 56, 1200.
[31] Chu, G.-B.; Li, C.-B. Org.Biomol. Chem. 2010, 8, 4716.
[32] Wang, L.-Y.; Chen, B.; Ren, L.-H.; Zhang, H.-Y.; Lü, Y.; Gao, S. Chin.J.Catal. 2015, 36, 19.
[33] Kodama, S.; Yoshida, J.; Nomoto, A.; Ueta, Y.; Yano, S.; Ueshima, M.; Ogawa, A. Tetrahedron Lett. 2010, 41, 2450.
[34] Neumann, R.; Levin, M.-J. J.Org.Chem. 1991, 56, 5707.
[35] Nakayama, K.; Hamamoto, M.; Nishiyama, Y.; Ishii, Y. Chem.Lett. 1993, 22, 1699.
[36] Reddy, J.-S.; Sayari, A. Catal.Lett. 1994, 28, 263.
[37] Maruyama, K.; Kusukawa, T.; Highchi, Y.; Nishinaga, A. Chem.Lett. 1991, 7, 1093.
[38] Zhao, S.; Liu, C.; Guo, Y.; Xiao, J.-C.; Chen, Q.-Y. J.Org. Chem. 2014, 79, 8926.
[39] Zhang, C.-H.; Zhao, P.-S.; Zhang, Z.-L.; Zhang, J.-W.; Yang, P.; Gao, P.; Gao, J.; Liu, D. RSC Adv. 2017, 7, 47366.
[40] Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. ChemCatChem 2010, 2, 1438.
[41] Zhang, E.; Tian, H.-W.; Xu, S.-D.; Yu, X.-C.; Xu, Q. Org.Lett. 2013, 15, 2704.
[42] Gopalaiah, K.; Saini, A. Catal.Lett. 2016, 146, 1648.
[43] Kim, S.-S.; Thakur, S.-S.; Song, J.-Y.; Lee, K.-H. Bull.Korean Chem.Soc. 2005, 26, 499.
[44] Choudary, B.-M.; Narender, N.; Bhuma, V. Synth.Commun. 1996, 26, 631.
[45] Ohtani, B.; Osaki, H.; Nishimoto, S.-I.; Kagia, T. Chem.Lett. 1985, 21, 1075.
[46] Lang, X.; Ji, H.; Chen, C.; Ma, W.; Zhao, J. Angew.Chem., Int.End. 2011, 50, 3934.
[47] Lang, X.; Ma, W.; Zhao, Y.; Chen, C.; Ji, H.; Zhao, J. Chem.-Eur. J. 2012, 18, 2624.
[48] Li, N.; Lang, X.-J.; Ma, W.-H.; Ji, H.-W.; Chen, C.-C.; Zhao, J.-C. Chem. Commun. 2013, 49, 5034.
[49] Bu, J.; Fang, J.; Leow, W.-R.; Zheng, K.-H.; Chen, X.-D. RSC Adv. 2015, 5, 103895.
[50] Dai, J.; Yang, J.; Wang, X.-H.; Zhang, L.; Li, Y. Appl.Surf.Sci. 2015, 349, 343.
[51] Zavahir, S.; Zhu, H. Molecules 2015, 20, 1941.
[52] Furukawa, S.; Ohno, Y.; Shishido, T.; Teramura, K.; Tanaka, T. ACS Catal. 2011, 1, 1150.
[53] Su, F.; Mathew, S.-C.; Möhlmann, L.; Antonietti, M.; Wang, X.; Blechert, S. Angew.Chem., Int.Ed. 2011, 50, 657.
[54] Park, J.-H.; Ko, K.-C.; Kim, E.; Park, N.; Ko, J.-H.; Ryu, D.-H.; Ahn, T.-K.; Lee, J.-Y.; Son, S.-U. Org. Lett. 2012, 14, 5502.
[55] Jin, J.; Shin, H.-W.; Park, J.-H.; Park, J.-H.; Kim, E.; Ahn, T.-K.; Ryu, D.-H.; Son, S.-U. Organometallics 2013, 32, 3954.
[56] Berlicka, A.; König, B. Photochem.Photobiol.Sci. 2010, 9, 1359.
[57] Naya, S.-I.; Kimura, K.; Tada, H. ACS Catal. 2013, 3, 10.
[58] Ye, L.; Li, Z.-H. ChemCatChem 2014, 6, 2540.
[59] Mure, M.; Klinman, J.-P. J.Am.Chem.Soc. 1995, 117, 8698.
[60] Mure, M.; Klinman, J.-P. J.Am.Chem. Soc. 1995, 117, 8707.
[61] Lee, Y.; Sayre, L.-M. J.Am.Chem.Soc. 1995, 117, 11823.
[62] Ling, K.-Q.; Kim, J.; Sayre, L.-M. J.Am.Chem. Soc. 2001, 123, 9606.
[63] Wendlandt, A.-E.; Stahl, S.-S. Org.Lett. 2012, 14, 2850.
[64] Yuan, H.; Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J.Am. Chem.Soc. 2012, 134, 13970.
[65] Yuan, Q.-L.; Zhou, X.-T.; Ji, H.-B. Catal. Commun. 2010, 12, 202.
[66] Tollari, S.; Fumagalli, A.; Porta, F. Inorg.Chim.Acta 1997, 247, 71.
[67] Kim, S.-S.; Thakur, S.-S.; Bull, K. Chem.Soc. 2005, 26, 1600.
[68] Zhou, X.-T.; Ren, Q.-G.; Ji, H.-B. Tetrahedron Lett. 2012, 53, 3369.
[69] Higuchi, M.; Ikeda, I.; Hirao, T. J.Org.Chem. 1997, 62, 1072.
[70] Huang, H.; Huang, J.; Liu, Y.-M.; He, H.-Y.; Cao, Y.; Fan, K.-N. Green Chem. 2012, 14, 930.
[71] Landge, S.-M.; Atanassova, V.; Thimmaiah, M.; Török, B. Tetrahedron Lett. 2007, 48, 5161.
[72] Liu, L.; Wang, Z.; Fu, X.; Yan, C.-H. Org. Lett. 2012, 14, 5692.

胺-胺氧化偶联合成亚胺的研究进展

Progress in Oxidative Coupling of Amines to Imines

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