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2021 , Vol. 41 >Issue 5: 1835 - 1850

DOI: https://doi.org/10.6023/cjoc202010020

综述与进展

过渡金属催化碳二亚胺环化的研究进展

  • 张震 ,
  • 畅温旭
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  • a 烟台大学化学化工学院 山东烟台 264005
    b 中国农业大学理学院 北京 100193

收稿日期: 2020-10-15

  修回日期: 2020-11-05

  网络出版日期: 2020-12-05

基金资助

烟台大学博士科研启动基金(HY19B07)

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Progress in Transition-Metal-Catalyzed Cyclization of Carbodiimides

  • Zhen Zhang ,
  • Wenxu Chang
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  • a College of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005
    b Department of Applied Chemistry, China Agricultural University, Beijing 100193
* Corresponding author. E-mail:

Received date: 2020-10-15

  Revised date: 2020-11-05

  Online published: 2020-12-05

Supported by

Doctoral Scientific Research Foundation of Yantai University(HY19B07)

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摘要

碳二亚胺是合成含氮分子最有效的前体之一. 过渡金属催化的碳二亚胺环化反应已成为合成杂环产物的有效方法, 并引起了合成化学和药物化学家的极大关注. 近些年发表的大量成果证明了该合成方法在现代有机合成中的重要性. 总结了该领域在过去十年中的研究进展及一些开拓性的工作. 根据不同的环化机理, 从三部分归纳和讨论了从碳二亚胺到系列杂环分子的合成方法, 主要包括由亲核过程引发的串联环化、基于碳二亚胺对环金属中间体插入过程的环化和含不饱和体系的碳二亚胺参与的协同环化.

关键词： 碳二亚胺; 过渡金属催化; 环化; 杂环; 杂累积双烯

本文引用格式

张震 , 畅温旭 . 过渡金属催化碳二亚胺环化的研究进展[J]. 有机化学, 2021 , 41(5) : 1835 -1850 . DOI: 10.6023/cjoc202010020

Abstract

Carbodiimide is one of the most efficient precursors to the synthesis of N-containing molecules. Transition-metal- catalyzed cyclization of carbodiimides has become a powerful approach to heterocyclic products, and attracts considerable attention from synthetical and pharmaceutical chemists. The significant amount of documents that were published during the last years proves the importance of this approach in modern organic synthesis. The development of this field over last decade and some pioneering work are summarized. An array of synthetic methods for privileged heterocycles from carbodiimides are presented according to mechanically distinctive processes: cascade cyclization initiated by nucleophilic process, catalytic cyclization via the insertion of carbodiimides into metal-cycle intermediates and annulation of tethered carbodiimides with unsaturated systems.

Key words： carbodiimide; transition-metal-catalysis; cyclization; heterocycle; heterocumulene

参考文献

[1]
(a) Vovk, M. V.; Samarai, L. I. Russ. Chem. Rev. 1992, 61, 297.
[1]
(b) Williams, A.; Ibrahim, I. T. Chem. Rev. 1981, 81, 589.
[1]
(c) Ulrich, H. Chemistry and Technology of Carbodiimides, John Wiley & Sons, Ltd, Chichester, UK, 2007.
[2]
(a) Zhang, W. X.; Hou, Z. Org. Biomol. Chem. 2008, 6, 1720.
[2]
(b) Alonso-Moreno, C.; Antinolo, A.; Carrillo-Hermosilla, F.; Otero, A. Chem. Soc. Rev. 2014, 43, 3406.
[2]
(c) Xu, L.; Zhang, W.-X.; Xi, Z. Organometallics 2015, 34, 1787.
[2]
(d) Zhang, W.-X.; Xu, L.; Xi, Z. Chem. Commun. 2015, 51, 254.
[2]
(e) Wang, L.; Chi, Y.; Zhang, W.; Xi, Z. Chin. J. Org. Chem. 2018, 38, 1341. (in Chinese).
[2]
(王连军, 迟樾, 张文雄, 席振峰, 有机化学, 2018, 38, 1341.)
[3]
Peshkov, V. A.; Pereshivko, O. P.; Nechaev, A. A.; Peshkov, A. A.; Van der Eycken, E. V. Chem. Soc. Rev. 2018, 47, 3861.
[4]
Wang, Y.; Zhang, W. X.; Xi, Z. Chem. Soc. Rev. 2020, 49, 5810.
[5]
Lv, X.; Bao, W. J. Org. Chem. 2009, 74, 5618.
[6]
(a) Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133.
[6]
(b) Yang, T.; Lin, C.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2005, 7, 4781.
[7]
He, H.-F.; Wang, Z.-J.; Bao, W. Adv. Synth. Catal. 2010, 352, 2905.
[8]
Huang, N. Y.; Liu, M. G.; Ding, M. W. J. Org. Chem. 2009, 74, 6874.
[9]
Lin, Y.; Li, E.; Wu, X.; Wang, L.; Wang, H.; Li, X.; Kang, H.; Zhou, L.; Shen, G.; Lv, X. Org. Biomol. Chem. 2020, 18, 1476.
[10]
(a) Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2012, 113, 1.
[10]
(b) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Rev. 2015, 115, 5301.
[11]
Zeng, F.; Alper, H. Org. Lett. 2010, 12, 1188.
[12]
(a) Domling, A. Chem. Rev. 2006, 106, 17.
[12]
(b) Lygin, A. V.; de Meijere, A. Angew. Chem., nt. Ed. 2010, 49, 9094.
[13]
Qiu, G.; Liu, G.; Pu, S.; Wu, J. Chem. Commun. 2012, 48, 2903.
[14]
Qiu, G.; Lu, Y.; Wu, J. Org. Biomol. Chem. 2013, 11, 798.
[15]
Larksarp, C.; Alper, H. J. Org. Chem. 1998, 63, 6229.
[16]
(a) Butler, D. C.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887.
[16]
(b) Zhou, H.-B.; Alper, H. Tetrahedron 2004, 60, 73.
[17]
Wang, F.; Cai, S.; Liao, Q.; Xi, C. J. Org. Chem. 2011, 76, 3174.
[18]
Shen, G.; Bao, W. Adv. Synth. Catal. 2010, 352, 981.
[19]
Duangjan, C.; Rukachaisirikul, V.; Saithong, S.; Kaeobamrung, J. Tetrahedron Lett. 2018, 59, 3537.
[20]
Han, M.-S.; Hahn, H.-G. Bull. Korean Chem. Soc. 2012, 33, 1371.
[21]
Larksarp, C.; Alper, H. J. Org. Chem. 2000, 65, 2773.
[22]
Chi, Y.; Xu, L.; Du, S.; Yan, H.; Zhang, W. X.; Xi, Z. Chem.-Eur. J. 2015, 21, 10369.
[23]
Lu, C.; Gong, C.; Zhao, B.; Hu, L.; Yao, Y. J. Org. Chem. 2018, 83, 1154.
[24]
Das, S.; Bhattacharjee, J.; Panda, T. K. Dalton Trans. 2019, 48, 7227.
[25]
Chi, Y.; Yan, H.; Zhang, W. X.; Xi, Z. Org. Lett. 2017, 19, 2694.
[26]
Pathare, R. S.; Ansari, A. J.; Verma, S.; Maurya, A.; Maurya, A. K.; Agnihotri, V. K.; Sharon, A.; Pardasani, R. T.; Sawant, D. M. J. Org. Chem. 2018, 83, 9530.
[27]
Zeng, F.; Alper, H. Org. Lett. 2010, 12, 3642.
[28]
Qiu, G.; He, Y.; Wu, J. Chem. Commun. 2012, 48, 3836.
[29]
Qiu, G.; Wu, J. Chem. Commun. 2012, 48, 6046.
[30]
Yuan, G.; Liu, H.; Gao, J.; Yang, K.; Niu, Q.; Mao, H.; Wang, X.; Lv, X. J. Org. Chem. 2014, 79, 1749.
[31]
Xu, B.; Peng, B.; Cai, B.; Wang, S.; Wang, X.; Lv, X. Adv. Synth. Catal. 2016, 358, 653.
[32]
Hao, W.; Sang, X.; Xiao, Y.; Cai, M. Tetrahedron Lett. 2016, 57, 4207.
[33]
Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 18, 1333.
[34]
Hoberg, H.; Burkhart, G. Synthesis 1979, 1979, 525.
[35]
Young, D. D.; Deiters, A. Angew. Chem., nt. Ed. 2007, 46, 5187.
[36]
Ishii, M.; Mori, F.; Tanaka, K. Chem.-Eur. J. 2014, 20, 2169.
[37]
Tanaka, K.; Mimura, M.; Hojo, D. Tetrahedron 2009, 65, 9008.
[38]
Raghuvanshi, A.; Singh, A. K.; Mobin, S. M.; Mathur, P. ChemistrySelect 2017, 2, 9245.
[39]
Zhang, Z.; Qin, Z.; Chang, W.; Li, J.; Fan, R.; Wu, X.; Guo, R.; Xie, X.; Zhou, L. Adv. Synth. Catal. 2020, 362, 2864.
[40]
Lee, E. E.; Rovis, T. Org. Lett. 2008, 10, 1231.
[41]
Li, Z.; Huo, T.; Li, L.; Feng, S.; Wang, Q.; Zhang, Z.; Pang, S.; Zhang, Z.; Wang, P.; Zhang, Z. Org. Lett. 2018, 20, 7762.
[42]
Wang, Y.; Li, Z.; Zhao, H.; Zhang, Z. Synthesis 2019, 51, 3250.
[43]
Tsukano, C.; Nakajima, M.; Hande, S. M.; Takemoto, Y. Org. Biomol. Chem. 2019, 17, 1731.
[44]
Saito, T.; Shiotani, M.; Otani, T.; Hasaba, S. Heterocycles 2003,60.
[45]
Saito, T.; Sugizaki, K.; Otani, T.; Suyama, T. Org. Lett. 2007, 9, 1239.
[46]
Mukai, C.; Yoshida, T.; Sorimachi, M.; Odani, A. Org. Lett. 2006, 8, 83.
[47]
Saito, T.; Furukawa, N.; Otani, T. Org. Biomol. Chem. 2010, 8, 1126.
[48]
Otani, T.; Saito, T.; Sakamoto, R.; Osada, H.; Hirahara, A.; Furukawa, N.; Kutsumura, N.; Matsuo, T.; Tamao, K. Chem. Commun. 2013, 49, 6206.
[49]
Tateno, K.; Ogawa, R.; Sakamoto, R.; Tsuchiya, M.; Kutsumura, N.; Otani, T.; Ono, K.; Kawai, H.; Saito, T. J. Org. Chem. 2018, 83, 690.
[50]
Otani, T.; Onishi, M.; Seino, T.; Furukawa, N.; Saito, T. RSC Adv. 2014, 4, 53669.
[51]
Zhang, Z.; Xiao, F.; Huang, B.; Hu, J.; Fu, B.; Zhang, Z. Org. Lett. 2016, 18, 908.
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