SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 11: 3517 - 3535

DOI: https://doi.org/10.6023/cjoc202003057

综述与进展

基于亚胺瞬态导向策略的过渡金属催化的碳氢键活化

  • 吴勇杰 ,
  • 史炳锋
展开
  • 浙江大学化学系 杭州 310027

收稿日期: 2020-03-25

  修回日期: 2020-04-30

  网络出版日期: 2020-05-11

基金资助

国家自然科学基金（Nos.21925109，21772170）、浙江省万人计划青年拔尖（No.ZJWR0108）、中央高校基本科研业务费（No.2018XZZX001-02）和浙江省自然科学基金（No.LR17B020001）资助项目.

收起

Transition Metal-Catalyzed C-H Activation via Imine-Based Transient Directing Group Strategy

  • Wu Yongjie ,
  • Shi Bingfeng
Expand
  • Department of Chemistry, Zhejiang University, Hangzhou 310027

Received date: 2020-03-25

  Revised date: 2020-04-30

  Online published: 2020-05-11

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21925109, 21772170), the Outstanding Young Talents of Zhejiang Province (No. ZJWR0108), the Fundamental Research Funds for the Central Universities (No. 2018XZZX001-02) and the Natural Science Foundation of Zhejiang Province (No. LR17B020001).

Fold

摘要

在过去几十年，过渡金属催化的碳氢键活化取得了巨大的发展，并给有机合成领域带来了革命性的改变.与传统的通过共价连接的导向基相比，基于瞬态导向策略的碳氢键活化，因为规避了传统导向基需要额外的步骤进行安装和脱除的不足，极大地提高了合成效率，拓宽了合成应用范围.综述了近年来基于亚胺瞬态导向策略的过渡金属催化的碳氢键活化的研究进展，着重探讨了各种瞬态导向基及其应用.按照底物类型和所活化碳氢键的类型进行分类，并对该领域目前存在的局限性和未来发展进行了总结和展望.

关键词： 瞬态导向策略; 过渡金属; 碳氢键活化; 亚胺; 导向基

本文引用格式

吴勇杰 , 史炳锋 . 基于亚胺瞬态导向策略的过渡金属催化的碳氢键活化[J]. 有机化学, 2020 , 40(11) : 3517 -3535 . DOI: 10.6023/cjoc202003057

Abstract

In the past decades, transition metal-catalyzed C—H activation has experienced tremendous growth and revolutionized the field of organic synthesis. Several elegant strategies have been developed to promote reactivity and control precise site-selectivity. Among which, transient directing group strategy has been recognized to be an efficient and powerful approach for selective C—H functionalization. In contrast to traditional directing groups with covalent linkage, transient directing group strategy circumvents the covalent installation and removal of directing groups, which significantly improve the synthetic efficiency and broaden the range of synthetic applications. The recent advances in imine-based transition directing groups are summarized, providing an overview of recent achievements in this cutting-edge research field over the past few years. For clarity, it is classified into two sections according to the type of substrate and the type of activated hydrocarbon bond. Emphasis is placed on the fully discussion of various transient directing groups and their applications. Finally, the limitations of previous works and perspectives on this cutting-edge area are also described.

Key words： transient directing group strategy; transition metal; C-H activation; imine; directing groups

参考文献

[1] (a) Godula, K.; Sames, D. Science 2006, 312, 67.
(b) Bergman, R. G. Nature 2007, 446, 391.
(c) Ellman, J. A.; Ackermann, L.; Shi, B. F. J. Org. Chem. 2019, 84, 12701.
[2] For recent reviews on C-H activation, see:(a) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(c) Pan, F.; Shi, Z. Acta Chim. Sinica 2012, 70, 1679(in Chinese). (潘菲, 施章杰, 化学学报, 2012, 70, 1679.)
(d) Yuan, Y.; Song, S.; Jiao, N. Acta Chim. Sinica 2015, 73, 1231(in Chinese). (袁逸之, 宋颂, 焦宁, 化学学报, 2015, 73, 1231.)
(e) Liu, B.; Hu, F.; Shi, B.-F. ACS Catal. 2015, 5, 1863.
(f) Huang, Z.; Lim, H. N.; Mo, F.; Young, M. C.; Dong, G. Chem. Soc. Rev. 2015, 44, 7764.
(g) Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053.
(h) He, G.; Wang, B.; Nack, W. A.; Chen, G. Acc. Chem. Res. 2016, 49, 635.
(i) Rao, W.-H.; Shi, B.-F. Org. Chem. Front. 2016, 3, 1028.
(j) Yang, Y.; Lan, J.; You, J. Chem. Rev. 2017, 117, 8787.
(k) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J.-Q. Chem. Rev. 2017, 117, 8754.
(l) Huang, J.; Gu, Q.; You, S.-L. Chin. J. Org. Chem. 2018, 38, 51(in Chinese). (黄家翩, 顾庆, 游书力, 有机化学, 2018, 38, 51.)
(m) Ren, Q.; Nie, B.; Zhang, Y.; Zhang, J. Chin. J. Org. Chem. 2018, 38, 2465(in Chinese). (任青云, 聂飚, 张英俊, 张霁, 有机化学, 2018, 38, 2465.)
(n) Zhao, K.; Yang, L.; Liu, J.; Xia, C. R. Chin. J. Org. Chem. 2018, 38, 2833(in Chinese). (赵康, 杨磊, 刘建华, 夏春谷, 有机化学, 2018, 38, 2833.)
(o) Xu, L.; Xu, H.; Lin, H.; Dai, H. Chin. J. Org. Chem. 2018, 38, 1940(in Chinese). (徐琳琳, 徐辉, 林海霞, 戴辉雄, 有机化学, 2018, 38, 1940.)
(p) Zhan, B.-B.; Shi, B.-F. Chin. J. Org. Chem. 2019, 39, 3602(in Chinese). (占贝贝, 史炳锋, 有机化学, 2019, 39, 3602.)
(q) Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 2192.
(r) Han, Y.-Q.; Zhou, T. Chin. J. Chem. 2020, 38, 527.
(s) Liu, Y.-H.; Xia, Y.-N.; Shi, B.-F. Chin. J. Chem. 2020, 38, 635.
[3] (a) Zhang, M.; Zhang, Y.; Jie, X.; Zhao, H.; Li, G.; Su, W. Org. Chem. Front. 2014, 1, 843.
(b) Sambiagio, C.; Schönbauer, D.; Blieck, R.; Dao-Huy, T.; Pototschnig, G.; Schaaf, P.; Wiesinger, T.; Zia, M. F.; Wencel-Delord, J.; Besset, T.; Maes, B. U. W.; Schnürch, M. Chem. Soc. Rev. 2018, 47, 6603.
(c) Zhang, Q.; Shi, B.-F. Chin. J. Chem. 2019, 37, 647.
(d) Rej, S.; Ano, Y.; Chatani, N. Chem. Rev. 2020, 120, 1788.
[4] (a) Besset, T.; Zhao, Q.; Poisson, T.; Pannecoucke, X. Synthesis 2017, 49, 4808.
(b) Qin, Y.; Zhu, L.; Luo, S. Chem. Rev. 2017, 117, 9433.
(c) Kim, D.-S.; Park, W.-J.; Jun, C.-H. Chem. Rev. 2017, 117, 8977.
(d) Gandeepan, P.; Ackermann, L. Chem 2018, 4, 199.
(e) Bhattacharya, T.; Pimparkar, S.; Maiti, D. RSC Adv. 2018, 8, 19456.
(f) St John-Campbell, S.; Bull, J. A. Org. Biomol. Chem. 2018, 16, 4582.
(g) Liao, G.; Wu, Y.-J.; Shi, B.-F. Acta Chim. Sinica 2020, 78, 289(in Chinese). (廖港, 吴勇杰, 史炳锋, 化学学报, 2020, 78, 289.)
[5] For selected examples of phosphites as transient directing groups, see:(a) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112.
(b) Bedford, R. B.; Limmert, M. E. J. Org. Chem. 2003, 68, 8669.
(c) Bedford, R. B.; Betham, M.; Caffyn, A. J.; Charmant, J. P.; Lewis-Alleyne, L. C.; Long, P. D.; Polo-Ceron, D.; Prashar, S. Chem. Commun. 2008, 990.
(d) Bedford, R. B.; Haddow, M. F.; Webster, R. L.; Mitchell, C. J. Org. Biomol. Chem. 2009, 7, 3119.
(e) Carrion, M. C.; Cole-Hamilton, D. J. Chem. Commun. 2006, 4527.
(f) Lewis, J. C.; Wu, J.; Bergman, R. G.; Ellman, J. A. Organometallics 2005, 24, 5737.
(g) Oi, S.; Watanabe, S.-I.; Fukita, S.; Inoue, Y. Tetrahedron Lett. 2003, 44, 8665.
(h) Yang, J. F.; Wang, R. H.; Wang, Y. X.; Yao, W. W.; Liu, Q. S.; Ye, M. Angew. Chem., Int. Ed. 2016, 55, 14116.
(i) Liu, Q.-S.; Wang, D.-Y.; Yang, J.-F.; Ma, Z.-Y.; Ye, M. Tetrahedron 2017, 73, 3591.
[6] Mo, F.; Dong, G. Science 2014, 345, 68.
[7] For selected examples of transient enamine directing groups, see:(a) Wang, Z.; Reinus, B. J.; Dong, G. J. Am. Chem. Soc. 2012, 134, 13954.
(b) Mo, F.; Lim, H. N.; Dong, G. J. Am. Chem. Soc. 2015, 137, 15518.
(c) Xu, Y.; Young, M. C.; Dong, G. J. Am. Chem. Soc. 2017, 139, 5716.
(d) Lim, H. N.; Dong, G. Angew. Chem., Int. Ed. 2015, 54, 15294.
(e) Xu, Y.; Su, T.; Huang, Z.; Dong, G. Angew. Chem., Int. Ed. 2016, 55, 2559.
[8] Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200.
[9] Jun, C.-H.; Lee, D.-Y.; Hong, J.-B. Tetrahedron Lett. 1997, 38, 6673.
[10] Vautravers, N. R.; Regent, D. D.; Breit, B. Chem. Commun. 2011, 47, 6635.
[11] Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884.
[12] Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem.-Eur. J. 2002, 8, 485.
[13] Kuninobu, Y.; Nishina, Y.; Shouho, M.; Takai, K. Angew. Chem., Int. Ed. 2006, 45, 2766.
[14] Chen, S.; Yu, J.; Jiang, Y.; Chen, F.; Cheng, J. Org. Lett. 2013, 15, 4754.
[15] Tan, P. W.; Juwaini, N. A. B.; Seayad, J. Org. Lett. 2013, 15, 5166.
[16] Li, G.; Jiang, J.; Xie, H.; Wang, J. Chem.-Eur. J. 2019, 25, 4688.
[17] Liu, X. H.; Park, H.; Hu, J. H.; Hu, Y.; Zhang, Q. L.; Wang, B. L.; Sun, B.; Yeung, K. S.; Zhang, F. L.; Yu, J. Q. J. Am. Chem. Soc. 2017, 139, 888.
[18] Chen, X. Y.; Ozturk, S.; Sorensen, E. J. Org. Lett. 2017, 19, 1140.
[19] Xu, J.; Liu, Y.; Wang, Y.; Li, Y.; Xu, X.; Jin, Z. Org. Lett. 2017, 19, 1562.
[20] Hu, W.; Zheng, Q.; Sun, S.; Cheng, J. Chem. Commun. 2017, 53, 6263.
[21] Li, B.; Seth, K.; Niu, B.; Pan, L.; Yang, H.; Ge, H. Angew. Chem., Int. Ed. 2018, 57, 3401.
[22] Wang, D. Y.; Guo, S. H.; Pan, G. F.; Zhu, X. Q.; Gao, Y. R.; Wang, Y. Q. Org. Lett. 2018, 20, 1794.
[23] Wang, Y. F.; Xu, W. G.; Sun, B.; Yu, Q. Q.; Li, T. J.; Zhang, F. L. J. Org. Chem. 2019, 84, 13104.
[24] Chen, X. Y.; Sorensen, E. J. J. Am. Chem. Soc. 2018, 140, 2789.
[25] (a) Li, F.; Zhou, Y.; Yang, H.; Liu, D.; Sun, B.; Zhang, F. L. Org. Lett. 2018, 20, 146.
(b) Zhan, B.-B.; Li, Y.; Xu, J.-W.; Nie, X.-L.; Fan, J.; Jin, L.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 5858.
[26] (a) Baudoin, O. Eur. J. Org. Chem. 2005, 4223.
(b) Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
(c) Wencel-Delord, J.; Panossian, A; Leroux, F. R.; Colobert, F. Chem. Soc. Rev. 2015, 44, 3418.
(d) Ma, G.; Sibi, M. P. Chem.-Eur. J. 2015, 21, 11644.
(e) Kumarasamy, E.; Raghunathan, R.; Sibi, M. P.; Sivaguru, J. Chem. Rev. 2015, 115, 11239.
(f) Mori, K.; Itakura, T.; Akiyama, T. Angew. Chem., Int. Ed. 2016, 55, 11642.
(g) Xu, C.; Zheng, H.; Hu, B.; Liu, X.; Liu, L.; Feng, X. Chem. Commun. 2017, 53, 9741.
(h) Zilate, B.; Castrogiovanni, A.; Sparr, C. ACS Catal. 2018, 8, 2981.
(i) Liao, G.; Zhou, T.; Yao, Q.-J.; Shi, B.-F. Chem. Commun. 2019, 55, 8514.
[27] (a) Yao, Q. J.; Zhang, S.; Zhan, B. B.; Shi, B. F. Angew. Chem., Int. Ed. 2017, 56, 6617.
(b) Fan, J.; Yao, Q. J.; Liu, Y. H.; Liao, G.; Zhang, S.; Shi, B. F. Org. Lett. 2019, 21, 3352.
[28] (a) Wang, Q.; Gu, Q.; You, S.-L. Angew. Chem., Int. Ed. 2019, 58, 6818.
(b) Chen, J.; Liu, Y. E.; Gong, X.; Shi, L.; Zhao, B. Chin. J. Chem. 2019, 37, 103.
(c) Gong, L.-Z. Sci. China:Chem. 2019, 62, 3.
(d) Li, S.; Chen, X.-Y.; Enders, D. Chem 2018, 4, 2026
[29] (a) Liao, G.; Yao, Q. J.; Zhang, Z. Z.; Wu, Y. J.; Huang, D. Y.; Shi, B. F. Angew. Chem., Int. Ed. 2018, 57, 3661.
(b) Liao, G.; Li, B.; Chen, H. M.; Yao, Q. J.; Xia, Y. N.; Luo, J.; Shi, B. F. Angew. Chem., Int. Ed. 2018, 57, 17151.
[30] Liao, G.; Chen, H. M.; Xia, Y. N.; Li, B.; Yao, Q. J.; Shi, B. F. Angew. Chem., Int. Ed. 2019, 58, 11464.
[31] Zhang, S.; Liao, G.; Shi, B. Chin. J. Org. Chem. 2019, 39, 1522(in Chinese). (张硕, 廖港, 史炳锋, 有机化学, 2019, 39, 1522.)
[32] (a) Zhang, S.; Yao, Q.-J.; Liao, G.; Li, X.; Li, H.; Chen, H.-M.; Hong, X.; Shi, B.-F. ACS Catal. 2019, 9, 1956.
(b) Chen, H.-M.; Zhang, S.; Liao, G.; Yao, Q.-J.; Xu, X.-T.; Zhang, K.; Shi, B.-F. Organometallics 2019, 38, 4022.
(c) Zhang, J.; Xu, Q.; Wu, J.; Fan, J.; Xie, M. Org. Lett. 2019, 21, 6361.
[33] Jin, L.; Yao, Q.-J.; Xie, P.-P.; Li, Y.; Zhan, B.-B.; Han, Y.-Q.; Hong, X.; Shi, B.-F. Chem 2020, 6, 497
[34] Song, H.; Li, Y.; Yao, Q. J.; Jin, L.; Liu, L.; Liu, Y. H.; Shi, B. F. Angew. Chem., Int. Ed. 2020, 59, 6576.
[35] Xu, J.; Liu, Y.; Zhang, J.; Xu, X.; Jin, Z. Chem. Commun. 2018, 54, 689.
[36] Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q. Science 2016, 351, 252.
[37] (a) Ma, F.; Lei, M.; Hu, L. Org. Lett. 2016, 18, 2708.
(b) Chen, J.; Bai, C.; Ma, H.; Liu, D.; Bao, Y.-S. Chin. Chem. Lett. 2020, DOI:10.1016/j.cclet.2020.02.055.
[38] Park, H.; Yoo, K.; Jung, B.; Kim, M. Tetrahedron 2018, 74, 2048.
[39] Tang, M.; Yu, Q.; Wang, Z.; Zhang, C.; Sun, B.; Yi, Y.; Zhang, F. L. Org. Lett. 2018, 20, 7620.
[40] Yang, K.; Li, Q.; Liu, Y.; Li, G.; Ge, H. J. Am. Chem. Soc. 2016, 138, 12775.
[41] St John-Campbell, S.; White, A. J. P.; Bull, J. A. Chem. Sci. 2017, 8, 4840.
[42] Hong, K.; Park, H.; Yu, J. Q. ACS Catal. 2017, 7, 6938.
[43] Pan, L.; Yang, K.; Li, G.; Ge, H. Chem. Commun. 2018, 54, 2759.
[44] Zhang, Y.-F.; Wu, B.; Shi, Z.-J. Chem.-Eur. J. 2016, 22, 17808.
[45] Mu, D.; Wang, X.; Chen, G.; He, G. J. Org. Chem. 2017, 82, 4497.
[46] Wang, X.; Song, S.; Jiao, N. Chin. J. Chem. 2018, 36, 213.
[47] Rasheed, O. Synlett 2018, 29, 1033.
[48] Huang, J.; Ding, J.; Ding, T. M.; Zhang, S.; Wang, Y.; Sha, F.; Zhang, S. Y.; Wu, X. Y.; Li, Q. Org. Lett. 2019, 21, 7342.
[49] Park, H.; Verma, P.; Hong, K.; Yu, J. Q. Nat. Chem. 2018, 10, 755.
[50] Chen, X. Y.; Ozturk, S.; Sorensen, E. J. Org. Lett. 2017, 19, 6280.
[51] Li, F.; Zhou, Y.; Yang, H.; Wang, Z.; Yu, Q.; Zhang, F.-L. Org. Lett. 2019, 21, 3692.
[52] Yong, Q.; Sun, B.; Zhang, F.-L. Tetrahedron Lett. 2019, 60, 151263.
[53] Qiao, H.; Sun, B.; Yu, Q.; Huang, Y.-Y.; Zhou, Y.; Zhang, F.-L. Org. Lett. 2019, 21, 6914.
[54] Wu, Y.-J.; Yao, Q.-J.; Chen, H.-M.; Liao, G.; Shi, B.-F. Sci. China:Chem. 2020, 63, 875.
[55] Liu, Y.; Ge, H. Nat. Chem. 2016, 9, 26.
[56] (a) Xu, J.-W.; Zhang, Z.-Z.; Rao, W.-H.; Shi, B.-F. J. Am. Chem. Soc. 2016, 138, 10750.
(b) Zhan, B.-B.; Li, Y.; Xu, J.-W.; Nie, X.-L.; Fan, J.; Jin, L.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 5858.
[57] Xu, Y.; Young, M. C.; Wang, C.; Magness, D. M.; Dong, G. Angew. Chem., Int. Ed. 2016, 55, 9084.
[58] Wu, Y.; Chen, Y. Q.; Liu, T.; Eastgate, M. D.; Yu, J. Q. J. Am. Chem. Soc. 2016, 138, 14554.
[59] Yada, A.; Liao, W.; Sato, Y.; Murakami, M. Angew. Chem., Int. Ed. 2017, 56, 1073.
[60] Chen, Y.-Q.; Wang, Z.; Wu, Y.; Wisniewski, S. R.; Qiao, J. X.; Ewing, W. R.; Eastgate, M. D.; Yu, J.-Q. J. Am. Chem. Soc. 2018, 140, 17884.
[61] (a) Vicente, J.; Saura-Llamas, I.; Palin, M. G.; Jones, P. G.; Ramírez de Arellano, M. C. Organometallics 1997, 16, 826.
(b) Largeron, M. Eur. J. Org. Chem. 2013, 2013, 5225.
(c) Corey, E. J.; Achiwa, K. J. Am. Chem. Soc. 1969, 91, 1429.
(d) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626.
(e) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
(f) Ryland, B. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2014, 53, 8824.
[62] (a) Liu, L.; Liu, Y.-H.; Shi, B.-F. Chem. Sci. 2020, 11, 290.
(b) Xu, J.-W.; Zhang, Z.-Z.; Rao, W.-H.; Shi, B.-F. J. Am. Chem. Soc. 2016, 138, 10750.
[63] Xiao, L.-J.; Hong, K.; Luo, F.; Hu, L.; Ewing, W. R.; Yeung, K.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2020, 59, 9594.
[64] (a) Chen, G.; Gong, W.; Zhuang, Z.; Andrä, M. S.; Chen, Y.-Q.; Hong, X.; Yang, Y.-F.; Liu, T.; Houk, K. N.; Yu, J.-Q. Science 2016, 353, 1023.
(b) Yan, S.-Y.; Han, Y.-Q.; Yao, Q.-J.; Nie, X.-L.; Liu, L.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 9093.
(c) Han, Y.-Q.; Ding, Y.; Zhou, T.; Yan, S.-Y.; Song, H.; Shi, B.-F. J. Am. Chem. Soc. 2019, 141, 4558.
(d) Zhou, T.; Jiang, M.-X.; Yang, X.; Yue, Q.; Han, Y.-Q.; Ding, Y.; Shi, B.-F. Chin. J. Chem. 2020, 38, 242.
Options
文章导航

/

〈 〉