SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 6: 1609 - 1625

DOI: https://doi.org/10.6023/cjoc202201047

综述与进展

可见光不对称催化合成手性氮杂芳烃衍生物

  • 尹艳丽 ,
  • 赵筱薇 ,
  • 江智勇
展开
  • a 河南工业大学生物工程学院 郑州 450001
    b 河南大学河南省手性化学国际联合基地 河南开封 475004
    b 河南师范大学化学化工学院 河南新乡 453007

收稿日期: 2022-01-28

  修回日期: 2022-02-21

  网络出版日期: 2022-03-03

基金资助

国家自然科学基金(22171072); 国家自然科学基金(21925103); 中国博士后科学基金(2020M680098)

收起

Asymmetric Photocatalytic Synthesis of Enantioenriched Azaarene Derivatives

  • Yanli Yin ,
  • Xiaowei Zhao ,
  • Zhiyong Jiang
Expand
  • a College of Bioengineering, Henan University of Technology, Zhengzhou 450001
    b International Scientific and Technological Cooperation Base of Chiral Chemistry, Henan University, Kaifeng, Henan 475004
    b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
*E-mail: ;

Received date: 2022-01-28

  Revised date: 2022-02-21

  Online published: 2022-03-03

Supported by

National Natural Science Foundation of China(22171072); National Natural Science Foundation of China(21925103); China Postdoctoral Science Foundation(2020M680098)

Fold

摘要

氮杂芳烃衍生物在众多领域尤其是医药和材料工业中的重要性吸引了化学家对发展其高效合成方法的持续关注. 迄今, 以市售氮杂芳烃或其简单衍生物作为原料, 且利用氮杂芳烃的电子性质引发化学转化的官能团化策略已被认为是一种强有力的工具. 其中, 由于具有条件温和、官能团耐受性良好且反应形式多样等优点, 可见光驱动光催化的方法被广泛探索. 值得注意的是, 许多针对含亚胺氮杂芳烃衍生物合成的反应类型的不对称版本被成功开发, 所获得的对映体纯产物具有令人满意的结果. 依据所构建手性中心相对氮杂芳烃的位置分四个部分总结, 并讨论这一重要领域的发展.

关键词： 可见光; 不对称光催化; 自由基加成; 质子化; 氮杂芳烃

本文引用格式

尹艳丽 , 赵筱薇 , 江智勇 . 可见光不对称催化合成手性氮杂芳烃衍生物[J]. 有机化学, 2022 , 42(6) : 1609 -1625 . DOI: 10.6023/cjoc202201047

Abstract

The importance of azaarene derivatives in many arenas, especially pharmaceutical and material industry, has attracted increasing attention of chemists to develop highly efficient synthetic methods. To date, functionalization of commercially available azaarenes and their simple derivatives as feedstocks by exploiting the electronic properties of azaarenes to trigger transformations has been appreciated as a powerful tool. Among them, due to the advantages of mild reaction conditions, good functional group tolerance and diverse reaction types, the methods via visible light-driven photocatalysis have been extensively explored. Notably, a number of asymmetric manifolds towards the synthesis of enantioenriched imine-containing azaarene derivatives have been established with satisfactory results. The advances of this important area are summarized and discussed according to the relative positions of the formed stereocenters to azaarenes.

Key words： visible light; asymmetric photocatalysis; radical addition; protonation; azaarene

参考文献

[1]
(a) Fréchet, J. M. J.; de Meftahi, M. V. Br. Polym. J. 1984, 16, 193.
[1]
(b) Majumdar, K. C.; Chattopadhyay, S. K. Heterocycles in Natural Product Synthesis, Wiley-VCH Verlag, Weinheim, 2011.
[1]
(c) Pozharskii, A. F.; Soldatenkov, A. T.; Katritzky, A. R. Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, John Wiley & Sons, Chichester, 2011.
[1]
(d) Li, J. J. Heterocyclic Chemistry in Drug Discovery, Ed.: Hoboken, N. J., John Wiley & Sons, Hoboken, New Jersey, 2013.
[1]
(e) Chelucci, G. Coord. Chem. Rev. 2013, 257, 1887.
[1]
(f) Guan, A.-Y.; Liu, C.-L.; Sun, X.-F.; Xie, Y.; Wang, M.-A. Bioorg. Med. Chem. 2016, 24, 342.
[1]
(g) Brown, D. G.; Wobst, H. J. J. Med. Chem. 2021, 64, 2312.
[2]
Boubertakh, O.; Goddard, J.-P. Eur. J. Org. Chem. 2017, 2017, 2072.
[3]
(a) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
[3]
(b) You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190.
[3]
(c) Evano, G.; Theunissen, C. Angew. Chem., Int. Ed. 2019, 58, 7558.
[3]
(d) Terrasson, V.; de Figueiredo, R. M.; Campagne, J. M. Eur. J. Org. Chem. 2010, 2010, 2635.
[4]
(a) Best, D.; Lam, H. W. J. Org. Chem. 2014, 79, 831.
[4]
(b) Xie, J.; Jin, H.; Hashmi, A. S. K. Chem. Soc. Rev. 2017, 46, 5193.
[4]
(c) Yin, Y.; Zhao, X.; Jiang, Z. ChemCatChem 2020, 12, 4471.
[4]
(d) Lv, X.; Xu, H.; Yin, Y.; Zhao, X.; Jiang, Z. Chin. J. Chem. 2020, 38, 1480.
[5]
(a) Proctor, R. S. J.; Phipps, R. J. Angew. Chem., Int. Ed. 2019, 58, 13666.
[5]
(b) Sun, A. C.; McAtee, R. C.; McClain, E. J.; Stephenson, C. R. J. Synthesis 2019, 51, 1063.
[5]
(c) Zhao, Y.; Xia, W. Org. Biomol. Chem. 2019, 17, 4951.
[5]
(d) Dong, J.; Liu, Y.; Wang, Q. Chin. J. Org. Chem. 2021, 41, 3771. (in Chinese)
[5]
董建洋, 刘玉秀, 汪清民, 有机化学, 2021, 41, 3771.)
[5]
For a selected example via visible-light-driven asymmetric catalytic construction strategy, see: (e) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 53, 3795.
[6]
(a) Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2008, 130, 14092.
[6]
(b) Trost, B. M.; Thaisrivongs, D. A. J. Am. Chem. Soc. 2009, 131, 12506.
[6]
(c) Izquierdo, J.; Landa, A.; Bastida, I.; López, R.; Oiarbide, M.; Palomo, C. J. Am. Chem. Soc. 2016, 138, 3282.
[6]
(d) Meazza, M.; Tur, F.; Hammer, N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2017, 56, 1634.
[6]
(e) Bai, X.; Zeng, G.; Shao, T.; Jiang, Z. Angew. Chem., Int. Ed. 2017, 56, 3684.
[7]
(a) Rupnicki, L; Saxena, A.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 10386.
[7]
(b) Pattison, G.; Piraux, G.; Lam, H. W. J. Am. Chem. Soc. 2010, 132, 14373.
[7]
(c) Saxena, A.; Lam, H. W. Chem. Sci. 2011, 2, 2326.
[7]
(d) Saxena, A.; Choi, B.; Lam, H. W. J. Am. Chem. Soc. 2012, 134, 8428.
[8]
(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[8]
(b) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898.
[8]
(c) Wei, G.; Basheer, C.; Tan, C.-H.; Jiang, Z. Tetrahedron Lett. 2016, 57, 3801.
[8]
(d) Zhao, H.; Cheng, D.; Xu, X. Chin, J. Org. Chem. 2021, 41, 642. (in Chinese)
[8]
( 赵赫, 程冬萍, 许孝良, 有机化学, 2021, 41, 642.)
[9]
(a) Wang, C.; Lu, Z. Org. Chem. Front. 2015, 2, 179.
[9]
(b) Meggers, E. Chem. Commun. 2015, 51, 3290.
[9]
(c) Brimioulle, R.; Lenhart, D.; Maturi, M. M.; Bach, T. Angew. Chem., Int. Ed. 2015, 54, 3872.
[9]
(d) Jiang, C.; Chen, W.; Zheng, W.-H.; Lu, H. Org. Biomol. Chem. 2019, 17, 8673.
[9]
(e) Yin, Y.; Zhao, X.; Qiao, B.; Jiang, Z. Org. Chem. Front. 2020, 7, 1283.
[9]
(f) Proctor, R. S. J.; Colgan, A. C.; Phipps, R. J. Nat. Chem. 2020, 12, 990.
[9]
(g) Yao, W.; Bazan-Bergamino, E. M.; Ngai, M.-Y. ChemCatChem 2022, 14, e202101292.
[10]
Minisci, F.; Galli, R.; Cecere, M.; Malatesta, V.; Caronna, T. Tetrahedron Lett. 1968, 9, 5609.
[11]
Cheng, W.-M.; Shang, R.; Fu, Y. ACS Catal. 2017, 7, 907.
[12]
Proctor, R. S. J.; Davis, H. J.; Phipps, R. J. Science 2018, 360, 419.
[13]
Ermanis, K.; Colgan, A. C.; Proctor, R. S. J.; Hadrys, B. W.; Phipps, R. J.; Goodman, J. M. J. Am. Chem. Soc. 2020, 142, 21091.
[14]
Reid, J. P.; Proctor, R. S. J.; Sigman, M. S.; Phipps, R. J. J. Am. Chem. Soc. 2019, 141, 19178.
[15]
Liu, X.; Liu, Y.; Chai, G.; Qiao, B.; Zhao, X.; Jiang, Z. Org. Lett. 2018, 20, 6298.
[16]
(a) Zhao, Y.; Zhang, C.; Chin, K. F.; Pytela, O.; Wei, G.; Liu, H.; Bureš, F.; Jiang, Z. RSC Adv. 2014, 4, 30062.
[16]
(b) Liu, X.; Ye, X.; Bureš, F.; Liu, H.; Jiang, Z. Angew. Chem., Int. Ed. 2015, 54, 11443.
[16]
(c) Liu, Y.; Li, J.; Ye, X.; Zhao, X.; Jiang, Z. Chem. Commun. 2016, 52, 13955.
[16]
(d) Wei, G.; Zhang, C.; Bureš, F.; Ye, X.; Tan, C.-H.; Jiang, Z. ACS Catal. 2016, 6, 3708.
[16]
(e) Zhang, C.; Li, S.; Bureš, F.; Lee, R.; Ye, X.; Jiang, Z. ACS Catal. 2016, 6, 6853.
[16]
(f) Shao, T.; Jiang, Z. Acta Chim. Sinica 2017, 75, 70. (in Chinese)
[16]
( 邵天举, 江智勇, 化学学报, 2017, 75, 70.)
[16]
(g) Bu, L.; Li, J.; Yin, Y.; Qiao, B.; Chai, G.; Zhao, X.; Jiang, Z. Chem.-Asian J. 2018, 13, 2382.
[17]
Fu, M.-C.; Shang, R.; Zhao, B.; Wang, B.; Fu, Y. Science 2019, 363, 1429.
[18]
Zheng, D.; Studer, A. Angew. Chem., Int. Ed. 2019, 58, 15803.
[19]
Proctor, R. S. J.; Chuentragool, P.; Colgan, A. C.; Phipps, R. J. J. Am. Chem. Soc. 2021, 143, 4928.
[20]
Mohr, J. T.; Hong, A. Y.; Stoltz, B. M. Nat. Chem. 2009, 1, 359.
[21]
Yin, Y.; Dai, Y.; Jia, H.; Li, J.; Bu, L.; Qiao, B.; Zhao, X.; Jiang, Z. J. Am. Chem. Soc. 2018, 140, 6083.
[22]
Tan, Y.; Yin, Y.; Cao, S.; Zhao, X.; Qu, G.; Jiang, Z. Chin. J. Catal. 2022, 43, 558.
[23]
Lin, L.; Bai, X.; Ye, X.; Zhao, X.; Tan, C.-H.; Jiang, Z. Angew. Chem., Int. Ed. 2017, 56, 13842.
[24]
Qiao, B.; Li, C.; Zhao, X.; Yin, Y.; Jiang, Z. Chem. Commun. 2019, 55, 7534.
[25]
Hou, M.; Lin, L.; Chai, X.; Zhao, X.; Qiao, B.; Jiang, Z. Chem. Sci. 2019, 10, 6629.
[26]
Shao, T.; Li, Y.; Ma, N.; Li, C.; Chai, G.; Zhao, X.; Qiao, B.; Jiang, Z. iScience 2019, 16, 410.
[27]
Yin, Y.; Li, Y.; Gonçalves, T. P.; Zhan, Q.; Wang, G.; Zhao, X.; Qiao, B.; Huang, K.-W.; Jiang, Z. J. Am. Chem. Soc. 2020, 142, 19451.
[28]
Li, J.; Kong, M.; Qiao, B.; Lee, R.; Zhao, X.; Jiang, Z. Nat. Commun. 2018, 9, 2445.
[29]
Nicewicz, D. A. D.; MacMillan, W. C. Science 2008, 322, 77.
[30]
Shih, H.-W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600.
[31]
Nacsa, E. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2018, 140, 3322.
[32]
Hepburn, H. B.; Melchiorre, P. Chem. Commun. 2016, 52, 3520.
[33]
Chai, X.; Hu, X.; Zhao, X.; Yin, Y.; Cao, S.; Jiang, Z. Angew. Chem., Int. Ed. 2022, 61, e202115110.
[34]
(a) Ajitha, M. J.; Huang, K.-W. Synthesis 2016, 48, 3449.
[34]
(b) Zhao, X.; Zhu, B.; Jiang, Z. Synlett 2015, 26, 2216.
[34]
(c) Tan, B.; Lu, Y.; Zeng, X.; Chua, P. J.; Zhong, G. Org. Lett. 2010, 12, 2682.
[34]
(d) Zhu, B.; Zhang, W.; Richmond, L.; Han, Z.; Yang, W.; Tan, D.; Huang, K.-W.; Jiang, Z. Angew. Chem., Int. Ed. 2013, 52, 6666.
[35]
Wang, S.; Li, X.; Liu, H.; Xu, L.; Zhuang, J.; Li, J.; Li, H.; Wang, W. J. Am. Chem. Soc. 2015, 137, 2303.
[36]
(a) Miyazawa, K.; Yasu, Y.; Koike, T.; Akita, M. Chem. Commun. 2013, 49, 7249.
[36]
(b) Miyazawa, K.; Koike, T.; Akita, M. Adv. Synth. Catal. 2014, 356, 2749.
[36]
(c) Nakajima, M.; Lefebvre, Q.; Rueping, M. Chem. Commun. 2014, 50, 3619.
[36]
(d) Lima, F.; Sharma, U. K.; Grunenberg, L.; Saha, D.; Johannsen, S.; Sedelmeier, J.; Van der Eycken, E. V.; Ley, S. V. Angew. Chem., Int. Ed. 2017, 56, 15136.
[36]
(e) Capaldo, L.; Fagnoni, M.; Ravelli, D. Chem.-Eur. J. 2017, 23, 6527.
[36]
(f) Lee, K. N.; Lei, Z.; Ngai, M.-Y. J. Am. Chem. Soc. 2017, 139, 5003.
[37]
Cao, K.; Tan, S. M.; Lee, R.; Yang, S.; Jia, H.; Zhao, X.; Qiao, B.; Jiang, Z. J. Am. Chem. Soc. 2019, 141, 5437.
[38]
(a) Streuff, J. Synthesis 2013, 45, 281.
[38]
(b) Ardisson, J.; Férézou, J. P.; Julia, M.; Pancrazi, A. Tetrahedron Lett. 1987, 28, 2001.
[38]
(c) Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821.
[38]
(d) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
[38]
(e) Porter, N. A.; Chang, V. H.-T.; Magnin, D. R.; Wright, B. T. J. Am. Chem. Soc. 1988, 110, 3554.
[38]
(f) Enholm, E. J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939.
[38]
(g) Enholm, E. J.; Burroff, J. A. Tetrahedron Lett. 1992, 33, 1835.
[38]
(h) Hays, D. S.; Fu, G. C. J. Org. Chem. 1996, 61, 4.
[38]
(i) Mikami, K.; Yamaoka, M. Tetrahedron Lett. 1998, 39, 4501.
[38]
(j) Tripp, J. C.; Schiesser, C. H.; Curran, D. P. J. Am. Chem. Soc. 2005, 127, 5518.
[38]
(k) Hays, D. S.; Fu, G. C. J. Org. Chem. 1998, 63, 6375.
[38]
(l) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 5763.
[38]
(m) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236.
[38]
(n) Corey, E. J.; Zheng, G. Z. Tetrahedron Lett. 1997, 38, 2045.
[38]
(o) Cossy, J.; Belotti, D. Tetrahedron 2006, 62, 6459.
[39]
Guo, Z.; Chen, X.; Fang, H.; Zhao, X.; Jiang, Z. Sci. China: Chem. 2021, 64, 1522.
[40]
Kong, M.; Tan, Y.; Zhao, X.; Qiao, B.; Tan, C.-H.; Cao, S.; Jiang, Z. J. Am. Chem. Soc. 2021, 143, 4024.
[41]
Hu, W.; Zhan, Q.; Zhou, H.; Cao, S.; Jiang, Z. Chem. Sci. 2021, 12, 6543.
Options
文章导航

/

〈 〉