综述与进展

钴催化C—H胺化反应的研究进展

  • 孙义明 ,
  • 丁奇峰 ,
  • 于杨 ,
  • 何益得 ,
  • 黄菲
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  • a 南京工业大学药学院 南京 211816;
    b 南京师范大学食品与制药工程学院 南京 210023;
    c 南京工业大学环境科学与工程学院 南京 211816

收稿日期: 2019-06-20

  修回日期: 2019-07-24

  网络出版日期: 2019-08-07

基金资助

中国博士后科学基金(No.2019M651809)、江苏省先进生物制造创新中心(Nos.XTE1850,XTC1810)、安徽省博士后科研活动经费(No.2018B252)和江苏省自然科学基金青年基金(No.BK20160989)资助项目.

Progress in Co-Catalyzed C-H Amination

  • Sun Yiming ,
  • Ding Qifeng ,
  • Yu Yang ,
  • He Yide ,
  • Huang Fei
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  • a College of Pharmacy, Nanjing Tech University, Nanjing 211816;
    b College of Food and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023;
    c School of Environmental and Engineering, Nanjing Tech University, Nanjing 211816

Received date: 2019-06-20

  Revised date: 2019-07-24

  Online published: 2019-08-07

Supported by

Project supported by the Postdoctoral Science Foundation of China (No. 2019M651809), the Jiangsu Synergetic Innovation Center for Advanced Bio-manufacture (Nos. XTE1850, XTC1810), the Postdoctoral Science Foundation of Anhui Province (No. 2018B252) and the Natural Science Foundation of Jiangsu Province (No. BK20160989).

摘要

胺基化合物在有机化学、药物化学和功能性材料领域中具有广泛的应用,C—N键的高效构筑具有重要的研究意义.传统的胺化反应构筑C—N键需要对底物进行预官能团化,并且不可避免地生成定量的卤代物副产物,而C—H胺化反应直接以碳氢化合物为原料,反应具有“步骤”及“原子”经济性高的优点,符合绿色化学理念.过渡金属钴具有低毒、廉价的优势,作为C—H胺化反应的催化剂展示了其独特的催化特性,吸引了化学家们的关注.主要总结近年来钴催化C—H胺化反应的研究进展,同时对该研究领域所面临的挑战和发展前景进行总结和展望.

本文引用格式

孙义明 , 丁奇峰 , 于杨 , 何益得 , 黄菲 . 钴催化C—H胺化反应的研究进展[J]. 有机化学, 2019 , 39(12) : 3363 -3374 . DOI: 10.6023/cjoc201906026

Abstract

Amino compounds have a wide range of applications in the fields of organic chemistry, medicinal chemistry and functional materials. The efficient construction of C-N bonds has important research significance. Conventional amination reactions to construct C-N bonds require pre-functionalization of the substrate and inevitably produce quantitative halogenate by-products. The C-H amination reaction is directly based on hydrocarbons. The reaction has the advantages of "step" and "atomic" economy, in line with the green chemistry concept. Transition metal cobalt has the advantage of low toxicity and low cost. As a catalyst for C-H amination reaction, it exhibits its unique catalytic properties and attracts the attention of chemists. The research progress of cobalt-catalyzed C-H amination in recent years is summarized. At the same time, the challenges and development prospects of the research field are summarized and forecasted.

参考文献

[1] (a) Ning, Z.; Tian, H. Chem. Commun. 2009, 5483.
(b) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166.
(c) Liu, D.; Zhang, Z.; Zhang, H.; Wang, Y. Chem. Commun. 2013, 49, 10001.
(d) Mphahlele, M. J.; Paumo, H. K.; El-Nahas, A. M.; ElHendawy, M. M. Molecules 2014, 19, 795.
(e) Lücking, U. Angew. Chem., Int. Ed. 2013, 52, 9399.
(f) Liu, L.-T.; Chen, Y.-Y.; Zhang, A.-A.; Liu, X.; Zhang, L.; Bai, J.-R.; Li, H.; Mao, G.-L. Chin. J. Org. Chem. 2019, 39, 475(in Chinese). (刘澜涛, 陈莹莹, 张安安, 刘雪, 张丽, 白静茹, 李恒, 毛国梁, 有机化学, 2019, 39, 475.)
[2] (a) Dillard, R.; Yen, T.; Stark, P.; Pavey, D. J. Med. Chem. 1980, 23, 717.
(b) Zhou, H.; Chen, Z.-Y. Chin. J. Org. Chem. 2018, 38, 719(in Chinese). (周豪, 陈知远, 有机化学, 2018, 38, 719.)
[3] Bartoszyk, G.; Dooley, D.; Barth, H.; Hartenstein, J.; Satzinger, G. J. Pharm. Pharmacol. 1987, 39, 407.
[4] (a) Achelle, S.; Rodríguez-Lopez, J.; Guen, F. R. J. Org. Chem. 2014, 79, 7564.
(b) Witt, A.; Bergman, J. Curr. Org. Chem. 2003, 7, 659.
[5] (a) Strohriegl, P.; Grazulevicius, J. V. Adv. Mater. 2002, 14, 1439.
(b) Nishimura, K.; Kobota, T.; Inada, H.; Shirota, Y. J. Mater. Chem. 1991, 1, 897
[6] (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
(b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
(c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
(d) Hartwig, J. F. Nature 2008, 455, 314.
[7] (a) Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247.
(b) Moselage, M.; Li, J.; Ackermann, L. ACS Catal. 2016, 6, 498.
(c) Zhao, F.-Q.; Yang, Q.; Zhang, J.-J.; Shi, W.-M.; Hu, H.-H.; Liang, F.; Wei, W.; Zhou, S.-L. Org. Lett. 2018, 20, 7753.
(d) Gao, F.; Han, X.; Li, C.-P.; Liu, L.-J.; Cong, Z.-Q.; Liu, H. RSC Adv. 2018, 8, 32659.
(e) Yetra, S. R.; Shen, Z.-G.; Wang, H.; Ackermann, L. Beilstein J. Org. Chem. 2018, 14, 1546.
(f) Wang, F.; Jin, L.; Kong, L.-H.; Li, X.-W. Org. Lett. 2017, 19, 1812.
(g) Mei, R.-H.; Loup, J.; Ackermann, L. ACS Catal. 2016, 6, 793.
(h) Zhang, L.-B.; Zhang, S.-K.; Wei, D.-H.; Zhu, X.-J.; Hao, X.-Q.; Su, J.-H.; Niu, J.-L.; Song, M.-P. Org. Lett. 2016, 18, 1318.
(i) Sun, J.-S.; Liu, M.; Zhang, J.; Dong, L. J. Org. Chem. 2018, 83, 10555.
[8] (a) Kuhl, N.; Schröder, N.; Glorius, F. Adv. Synth. Catal. 2014. 356 1443.
(b) Song, G.; Li, X. Acc. Chem. Res. 2015. 48 1007.
(c) Newton, C. G.; Wang, S.-G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017. 117, 8908.
(d) Hummel, J. R.; Boerth, J. A.; Ellman, J. A. Chem. Rev. 2017. 117, 9163.
[9] (a) Gandeepan, P.; Cheng, C. H. Acc. Chem. Res. 2015, 48, 1194.
(b) Grigorjeva, L.; Daugulis, O. Org. Lett. 2014, 16, 4684.
(c) Prakash, S.; Muralirajan, K.; Cheng, C. H. Angew. Chem., Int. Ed. 2016, 55, 1844.
(d) Zhang, Z.-Z.; Liu, B.; Xu, J.-W.; Yan, S.-Y.; Shi, B.-F. Org. Lett. 2016, 18, 1776.
(e) Wei, D.-H.; Zhu, X.-J.; Niu, J.-L.; Song, M.-P. ChemCatChem 2016, 8, 1242.
(f) Shin, K.; Kim, H.; Chang, S. Acc. Chem. Res. 2015, 48, 1040.
(g) Kim, H.; Chang, S. ACS Catal. 2016, 6, 2341.
(h) Gu, Z.-Y.; Ji, S.-J. Acta Chim. Sinica 2018, 76, 347(in Chinese). (顾正洋, 纪顺俊, 化学学报, 2018, 76, 347.)
(i) Zhang, J.-H.; Hao, X.-Q.; Wang, Z.-L.; Ren, C.-J.; Niu, J.-L.; Song, M.-P. Chin. J. Org. Chem. 2017, 37, 1237(in Chinese). (张家恒, 郝新奇, 王正龙, 任常久, 牛俊龙, 宋毛平, 有机化学, 2017, 37, 1237.)
(j) Cheng, B.; Lu, P.; Zhao, J.-J.; Lu, Z. Chin. J. Org. Chem. 2019, 39, 1704(in Chinese). (程彪, 陆鹏, 赵家金, 陆展, 有机化学, 2019, 39, 1704.)
[10] (a) Park, J.; Chang, S. Angew. Chem., Int. Ed. 2015, 54, 14103.
(b) Liang, Y.-J.; Liang, Y.-F.; Tang, C.-H.; Yuan, Y.-Z.; Jiao, N. Chem. Eur. J. 2015, 21, 16395.
(d) Wu, F.-F.; Zhao, Y.; Chen, W.-Z. Tetrahedron 2016, 72, 8004.
(e) Wang, F.; Wang, H.; Wang, Q.; Yu, S.-J.; Li, X.-W. Org. Lett. 2016, 18, 1306.
(g) Figg, T. M.; Park, S.; Park, J.; Chang, S.; Musaev, D. G. Organometallics 2014, 33, 4076.
(h) Liu, Y.; Xie, F.; Jia, A.-Q.; Li, X.-W. Chem. Commun. 2018, 54, 4345.
(i) Bera, S. S.; Sk, M. R.; Maji, M. S. Chem. Eur. J. 2019, 25, 1806.
(j) Yan, Q.-Q.; Xiao, T.-X.; Liu, Z.-X.; Zhang, Y.-H. Adv. Synth. Catal. 2016, 358, 2707.
(k) Cheng, H.-C.; Hernández, J. G.; Bolm, C. Adv. Synth. Catal. 2018, 360, 1.
(l) Borah, G.; Borah, P.; Patel, P. Org. Biomol. Chem. 2017, 15, 3854.
(m) Yu, X.-L.; Ma, Q.; Lv, S.-Y.; Li, J.; Zhang, C.; Hai, L.; Wang, Q.-T.; Wu, Y. Org. Chem. Front. 2017, 4, 2184.
(n) Shi, P.-F.; Wang, L.-L.; Chen, K.-H.; Wang, J.; Zhu, J. Org. Lett. 2017, 19, 2418.
[11] (a) Villanueva, O.; Weldy, N. M.; Blakey, S. B.; MacBeth, C. E. Chem. Sci. 2015, 6, 6672.
(b) Harden, J. D.; Ruppel, J. V.; Gao, G.-Y.; Zhang, X. P. Chem. Commun. 2007, 4644.
(c) Pang, S.-F.; Yuan, H.-K.; Wu, Y.-J.; Shi, F. J. Mol. Catal. 2017, 31, 105(in Chinese). (庞少峰, 袁航空, 吴亚娟, 石峰, 分子催化, 2017, 31, 105.)
(d) Wu, X.-S.; Yang, K.; Zhao, Y.; Sun, H.; Li, G.-G.; Ge, H.-B. Nat. Commun. 2015, 6, 6462.
(e) Lu, H.-J.; Li, C.-Q.; Jiang, H.-L.; Lizardi, C. L.; Zhang, X. P. Angew. Chem., Int. Ed. 2014, 53, 7028.
(f) Lu, H.-J.; Zhang, X. P. Chem. Soc. Rev. 2011, 40, 1899.
(g) Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Gotti, C. L.; Lapadula, M.; Mangioni, E.; Cenini, S. Chem. Eur. J. 2003, 9, 249.
(h) Cenini, S.; Tollari, S.; Penoni, A.; Cereda C. J. Mol. Catal. 1999, 137, 135.
(i) Ruppel, J. V.; Kamble, R. M.; Zhang, X. P. Org. Lett. 2007, 9, 4889.
(j) Lu, H.-J.; Tao, J.; Jones, J. E.; Wojtas, L.; Zhang, X. P. Org. Lett. 2010, 12, 1248.
(k) Lu, H.-J.; Subbarayan, V.; Tao, J.; Zhang, X. P. Organometallics 2010, 29, 389.
(l) Cenini, S.; Gallo, E.; Penoni, A.; Ragainia, F.; Tollari, S. Chem. Commun. 2000, 2265.
(m) Tan, P.-W.; Mak, A. M.; Sullivan, M. B.; Dixon, D. J.; Seayad, J. Angew. Chem., Int. Ed. 2017, 56, 16550.
(n) Lu, H.-J.; Jiang, H.-L.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2010, 49, 10192.
[12] Patel, P.; Chang, S. ACS Catal. 2015, 5, 853.
[13] Wang, X.-M.; Lerchen, A.; Glorius, F. Org. Lett. 2016, 18, 2090.
[14] Wang, H.; Lorion, M.-M.; Ackermann, L. Angew. Chem., Int. Ed. 2016, 55, 10386.
[15] Huang, J.-p.; Huang, Y.-F.; Wang, T.; Huang, Q.; Wang, Z.-H.; Chen, Z.-Y. Org. Lett. 2017, 19, 1128.
[16] Du, C.; Li, P.-X.; Zhu, X.-J.; Han, J.-N.; Niu, J.-L.; Song, M.-P. ACS Catal. 2017, 7, 2810.
[17] Sauermann, N.; Mei, R.-H.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 5090.
[18] (a) Parry, J. B.; Fu, N.; Lin, S. Synlett 2018, 29, 257.
(b) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
(c) Feng, R.; Smith, J. A.; Moeller, K. D. Acc. Chem. Res. 2017, 50, 2346.
(d) Jiao, K.-J.; Zhao, C.-Q.; Fang, P.; Mei, T.-S. Tetrahedron Lett. 2017, 58, 797.
(e) Hou, Z.-W.; Mao, Z.-Y.; Xu, H.-C. Synlett 2017, 28, 1867.
[19] Sun, B.; Yoshino, T.; Matsunaga, S.; Kanai, M. Adv. Synth. Catal. 2014, 356, 1491.
[20] Li, W.; Weng, L.; Jin, G. Inorg. Chem. Commun. 2004, 7, 1174.
[21] Sun, B.; Yoshino, T.; Matsunaga, S.; Kanai, M. Chem. Commun. 2015, 51, 4659.
[22] Gao, X.-L.; Wang, P.; Zeng, L.; Tang, S.; Lei, A.-W. J. Am. Chem. Soc. 2018, 140, 4195.
[23] Wang, S.-B.; Gu, Q.; You, S.-L. J. Catal. 2018, 361, 393.
[24] Huang, D.-Y.; Yao, Q.-J.; Zhang, S.; Xu, X.-T.; Zhang, K.; Shi, B.-F. Org. Lett. 2019, 21, 951.
[25] Lu, H.-J.; Hu, Y.; Jiang, H.-L.; Wojtas, L.; Zhang, X. P. Org. Lett. 2012, 14, 5158.
[26] Luo, Y.-R. In Comprehensive Handbook of Chemical Bond Energies, Vol. 3, Ed.:Luo, Y.-R., Taylor & Francis Group, Boca Raton, 2007, p. 19.
[27] Barsu, N.; Rahman, M. A.; Sen, M.; Sundararaju B. Chem. Eur. J. 2016, 22, 9135.
[28] Lu, H.-J.; Lang, K.; Jiang, H.-L.; Wojtas, L.; Zhang, X. P. Chem. Sci. 2016, 7, 6934.
[29] Li, C.-Q.; Lang, K.; Lu, H.-J.; Hu, Y.; Cui, X.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2018, 57, 16837.
[30] Fukagawa, S.; Kato, Y.; Tanaka, R.; Kojima, M.; Yoshino, T.; Matsunaga. S. Angew. Chem., Int. Ed. 2019, 58, 1153.
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