SIOC English
有机化学
高级检索

有机化学 >

2018 , Vol. 38 >Issue 8: 1859 - 1871

DOI: https://doi.org/10.6023/cjoc201804033

综述与进展

亚胺参与的C-H键官能化/环化反应研究

  • 陈训 ,
  • 白丽丽 ,
  • 曾伟
展开
  • a 海南医学院药学院 海口 571199;
    b 华南理工大学化学与化工学院 广州 510640

收稿日期: 2018-04-16

  修回日期: 2018-05-04

  网络出版日期: 2018-05-17

基金资助

国家自然科学基金（No.21372085）、广州市科技计划（No.156300075）及清远市科技计划（No.2014D006）资助项目.

收起

Recent Advances in C-H Bond Functionalization/Cyclization Involving Imines

  • Chen Xun ,
  • Bai Lili ,
  • Zeng Wei
Expand
  • a School of Pharmacy, Hainan Medical University, Haikou 571199;
    b School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640

Received date: 2018-04-16

  Revised date: 2018-05-04

  Online published: 2018-05-17

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372085), the Science and Technology Program of Guangzhou City (No. 156300075) and the Science and Technology Program of Qingyuan (No. 2014D006).

Fold

摘要

过渡金属催化的C-H键官能团化策略因其高原子和步骤经济性而备受关注.亚胺因其多样性的反应活性而在构建结构新颖的含氮化合物中得以广泛应用，侧重综述了近年来亚胺参与的C-H键官能团化/环化反应的最新研究进展，并对其反应类型和相关机理予以论述.

关键词： 亚胺; 过渡金属催化; C-H键官能化; 氮杂环化合物

本文引用格式

陈训 , 白丽丽 , 曾伟 . 亚胺参与的C-H键官能化/环化反应研究[J]. 有机化学, 2018 , 38(8) : 1859 -1871 . DOI: 10.6023/cjoc201804033

Abstract

Transition metal-catalyzed direct C-H bond functionalization strategy has aroused wide concerns due to its high atom-economy and step-economy. Imine synthons exhibit diverse reactivities and are commonly employed to assemble nitrogen-containing complex molecules through direct C-H functionalization strategies, their reaction types and mechanisms are summarized in this paper.

Key words： imines; transition metal-catalysis; C-H bond functionalization; azaheterocycles

参考文献

[1] (a) Dolzhenko, A. V.; Chui, W. K. Heterocycles 2008, 75, 1575.
(b) Gundla, R.; Kazemi, R.; Sanam, R.; Muttineni, R.; Sarma, J. A. R. P.; Dayam, R.; Neamati, N. J. Med. Chem. 2008, 51, 3367.
(c) Van Horn, K. S.; Burda, W. N.; Fleeman, R.; Shaw, L. N.; Manetsch, R. J. Med. Chem. 2014, 57, 3075.
[2] (a) Zhang, J.; Liu, J.; Ma, Y.; Cheng, P. Chin. J. Org. Chem. 2017, 37, 555(in Chinese). (张金, 刘佳, 马养民, 程佩, 有机化学, 2017, 37, 555.)
(b) Zhang, Z.; Zheng, X.; Guo, C. Chin. J. Org. Chem. 2016, 36, 1241(in Chinese). (张钊瑞, 郑晓霖, 郭长彬, 有机化学, 2016, 36, 1241.)
[3] (a) Ramirez T. A.; Zhao B.; Shi Y. Chem. Soc. Rev. 2012, 41, 931.
(b) Wang, S.; Yan, F.; Wang, L.; Zhu, L. Chin. J. Org. Chem. 2018, 38, 291(in Chinese). (汪珊, 严沣, 汪连生, 朱磊, 有机化学, 2018, 38, 291.)
(c) Chen, J.; Hu, X.; Lu, L.; Xiao, W. Chem. Rev. 2015, 115, 5301.
[4] (a) Lamas, M. C.; Vaillard, S. E.; Wibbeling, B.; Studer, A. Org. Lett. 2010, 12, 2072.
(b) Ricardo, G. P.; Kiyoi, T.; Whiting, A. Org. Biomol. Chem. 2011, 9, 3105.
(c) Rishikesh, N.; Potowski, M.; Jia, Z. J.; Antonchick, A. P.; Waldmann, H. Acc. Chem. Res. 2014, 47, 1296.
[5] (a) Xiao, X.; Zhang, W.; Lu, X.; Deng, Y.; Jiang, H.; Zeng, W. Adv. Synth. Catal. 2016, 358, 2497.
(b) Dang, L.; Liang, L.; Qian, C.; Fu, M.; Ma, T.; Xu, D.; Jiang, H.; Zeng, W. J. Org. Chem. 2014, 79, 769.
(c) Fu, S.; Jiang, H.; Deng, Y.; Zeng, W. Adv. Synth. Catal. 2011, 353, 2795.
(d) Zhu, S.; Lu, X.; Luo, Y.; Zhang, W.; Jiang, H.; Yan, M.; Zeng, W. Org. Lett. 2013, 15, 1440.
(e) Zhu, S.; Dong, J.; Fu, S.; Jiang, H.; Zeng, W. Org. Lett. 2011, 13, 4914.
(f) Chen, J.; Lu, X.; Lou, W.; Ye, Y.; Jiang, H.; Zeng, W. J. Org. Chem. 2012, 77, 8541.
(g) Luo, Y.; Lu, X.; Ye, Y.; Guo, Y.; Jiang, H.; Zeng, W. Org. Lett. 2012, 14, 5640.
[6] Li, Q.; Wang, Y.; Hu, M.; Chen, P.; You, W.; Zhao, P. Chin. J. Org. Chem. 2017, 37, 967(in Chinese). (黎秋, 汪雨, 胡孟金, 陈鹏, 游文玮, 赵培亮, 有机化学, 2017, 37, 967.)
[7] Wei, Y.; Deb, I.; Yoshikai, N. J. Am. Chem. Soc. 2012, 134, 9098.
[8] Chen, Z.; Lu, B., Ding, Z.; Gao, K.; Yoshikai, N. Org. Lett. 2013, 15, 1966.
[9] Meng, L.; Wu, K.; Liu, C.; Lei, A. Chem. Commun. 2013, 52, 5853.
[10] Shi, Z.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 4892.
[11] Wu, K.; Meng, L.; Huai, M.; Huang, Z.; Liu, C.; Qi, X.; Lei, A. Chem. Commun. 2017, 53, 2294.
[12] Cappelli, A.; Giuliani, G.; Anzini, M.; Riitano, D.; Giorgi, G.; Vomero, S. Bioorg. Med. Chem. 2008, 16, 6850.
[13] Li, M.; Xie, Y.; Ye, Y.; Zou, Y.; Jiang, H.; Zeng, W. Org. Lett. 2014, 16, 6232.
[14] Xiao, X.; Xie, Y.; Bai, S.; Deng, Y.; Jiang, H.; Zeng, W. Org. Lett. 2015, 17, 3998.
[15] Bagdi, A. K.; Rahman, M.; Santra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2015, 355, 1741.
[16] Zhang, Y.; Chen, Z.; Wu, W.; Zhang, Y.; Su, W. J. Org. Chem. 2013, 78, 12494.
[17] Xie, Y.; Chen, T.; Fu, S.; Li, X.; Deng, Y.; Jiang, H.; Zeng, W. Chem. Commun. 2014, 50, 10699.
[18] Xie, Y.; Chen, T.; Fu, S.; Jiang, H.; Zeng, W. Chem. Commun. 2015, 51, 9377.
[19] Wang, L.; Li, Z.; Wang, K.; Xu, X.; Hu, S.; Wang, F. Chin. J. Org. Chem. 2016, 36, 889(in Chinese). (王亮, 李站, 万康, 瞿星, 胡思前, 王锋, 有机化学, 2016, 36, 889.)
[20] Chen, X.; Xie, Y.; Xiao, X.; Li, G.; Deng, Y.; Jiang, H.; Zeng, W. Chem. Commun. 2015, 51, 15328.
[21] Tan, W. W.; Yoshikai, N. Chem. Sci. 2015, 6, 6448.
[22] Barluenga, J.; Jimenez-Aquino, A.; Aznar, F.; Valdes, C. Chem. Eur. J. 2010, 16, 11707.
[23] Pham, N. N.; Dang, T. T.; Ngo, N. T. Villinger, A.; Ehlers, P.; Langer, P. Org. Biomol. Chem. 2015, 13, 6047.
[24] Chen, J.; Qu, H.; Peng, J.; Chen, C. Chin. J. Org. Chem. 2015, 35, 937(in Chinese). (陈静, 曲红梅, 彭静, 陈超, 有机化学, 2015, 35, 937.)
[25] Lu, B.; Wu, J.; Yoshikai, N. J. Am. Chem. Soc. 2014, 136, 11598.
[26] Wu, J.; Yoshikai, N. Angew. Chem. Int. Ed. 2015, 54, 11107.
[27] Deng, G. B.; Zhang, J. L.; Liu, Y. Y.; Liu, B.; Yang, X. H.; Li, J. H. Chem. Commun. 2015, 51, 1886.
[28] Chen, F.; Huang, X.; Li, X.; Shen, T.; Zou, M.; Jiao, N. Angew. Chem. Int. Ed. 2014, 53, 10495.
[29] Chen, T.; Chen, X.; Wei, J.; Lin, D.; Xie, Y.; Zeng, W. Org. Lett. 2016, 18, 2078.
[30] Guimond, N.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050.
[31] Wei, X.; Zhao, M.; Du, Z.; Li, X. Org. Lett. 2011, 13, 4636.
[32] Zhang, S.; Liu, X.; Chen, S.; Tan, D.; Jiang, C.; Wu, J.; Li, Q.; Wang, H. Adv. Synth. Catal. 2016, 358, 1705.
[33] He, R.; Huang, Z.; Zheng, Q.; Wang, C. Angew. Chem., Int. Ed. 2014, 53, 4950.
[34] Badra, K.; Kumar, G. S. Med. Res. Rev. 2011, 31, 821.
[35] Jayakumar, J.; Parthasarathy, K.; Cheng, C. H. Angew. Chem., Int. Ed. 2012, 124, 201.
[36] Lao, Y.; Zhang, S.; Liu, X.; Jiang, C.; Wu, J.; Li, Q.; Huang, Z.; Wang, H. Adv. Synth. Catal. 2016, 358, 2186.
[37] Zhang, W.; Wang, C.; Lin, H.; Dong, L.; Xu, Y. Chem.-Eur. J. 2016, 22, 907.
[38] Tran, D. N.; Cramer, N. Angew. Chem., Int. Ed. 2012, 122, 8357.
[39] Liang, Yu.; Müller, V.; Liu, W.; Münch, A.; Stalke, D.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 9415.
[40] Manikandan, R.; Tamizmani, M.; Jeganmohan, M. Org. Lett. 2017, 19, 6678.
[41] Wang, H.; Lorion, M. M.; Ackermann, L. ACS Catal. 2017, 7, 3430.
[42] Li, X.; Li, X.; Jiao, N. J. Am. Chem. Soc. 2015, 137, 9246.
[43] Gao, B.; Liu, S.; Lan, Y.; Huang, H. Organometallics 2016, 35, 1480.
[44] Wang, J.; Zha, S.; Chen, K.; Zhang, F.; Zhu, J. Org. Biomol. Chem. 2016, 14, 4848.
[45] Kim, J. H.; Greßies, S.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55, 5577.
[46] Li, X.; Sun, M.; Jin, Q.; Liu, K.; Liu, P. N. J. Org. Chem. 2016, 81, 3901.
[47] Wang, H.; Li, L.; Yu, S.; Li, Y.; Li, X. Org. Lett. 2016, 18, 2914.
[48] Chen, X.; Liu, X.; Su, S. J.; Li, J.; Zeng, W. Chem. Commun. 2016, 52, 5856.
[49] Cenini, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.; Piangiolino, C. Coord. Chem. Rev. 2006, 250, 1234.
[50] Yu, D. G.; Suri, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 8802.
[51] Peng, J.; Xie, Z.; Chen, M.; Wang, J.; Zhu, Q. Org. Lett. 2014, 16, 4702.
[52] Lian, Y.; Hummel, J. R.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2013, 135, 12548.
[53] Wang, X.; Jiao, N. Org. Lett. 2016, 18, 2150.
[54] Park, Y.; Park, K. T.; Kim, J. G.; Chang, S. J. Am. Chem. Soc. 2015, 137, 4534.
[55] Wang, J.; Zha, S.; Chen, K.; Zhang, F.; Song, C.; Zhu, J. Org. Lett. 2016, 18, 2062.
[56] Wang, F.; Wang, H.; Wang, Q.; Yu, S.; Li, X. Org. Lett. 2016, 18, 1306.
[57] Wang, X.; Lerchen, A.; Glorius, F. Org. Lett. 2016, 18, 2029.
[58] Wang, H.; Lorion, M. M.; Ackermann, L. Angew. Chem., Int. Ed. 2016, 55, 10386.
[59] Yu, S.; Tang, G.; Li, Y.; Zhou, X.; Lan, Y.; Li, X. Angew. Chem., Int. Ed. 2016, 55, 8696.
[60] Li, L.; Wang, H.; Yu, S.; Yang, X.; Li, X. Org. Lett. 2016, 18, 3662.
[61] Wang, Q.; Li, X. Org. Lett. 2016, 18, 2102.
[62] (a) Zhu, R.-Y.; Liu, L.-Y.; Yu, J.-Q. J. Am. Chem. Soc. 2017, 139, 12394.
(b) Xu, J.; Liu, Y.; Wang, Y.; Li, Y.; Xu, X.; Jin, Z. Org. Lett. 2017, 19, 1562.
(c) Yao, Q.-J.; Zhang, S.; Zhan, B.-B.; Shi, B.-F. Angew. Chem., Int. Ed. 2017, 56, 6617.
(d) Wu, Y.; Chen, Y.-Q.; Liu, T.; Eastgate, M. D.; Yu, J.-Q. J. Am. Chem. Soc. 2016, 138, 14554.
(e) Liu, Y.; Ge, H. Nat. Chem. 2016, 9, 26.
(f) Xu, Y.; Young, M. C.; Dong, G. J. Am. Chem. Soc. 2017, 139, 5716.
(g) Yada, A.; Liao, W.; Sato, Y.; Murakami, M. Angew. Chem., Int. Ed. 2017, 56, 1073.
[63] Chen, X. Y.; Ozturk, S.; Sorensen, E. J. Org. Lett. 2017, 19, 1140.
[64] Hu, W.; Zheng, Q.; Sun, S.; Cheng, J. Chem. Commun. 2017, 53, 6263.
[65] Shen, J.; Liu, X.; Wang, L.; Chen, Q.; He, M. Synth. Commun. 2018, 9, 1.
[66] Tan, P. W.; Juwaini, N. A. B.; Seayad, J. Org. Lett. 2013, 15, 5166.

Options
文章导航

/

〈 〉