Chinese Journal of Organic Chemistry >
Asymmetric Photocatalytic Synthesis of Enantioenriched Azaarene Derivatives
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)
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
Yanli Yin , Xiaowei Zhao , Zhiyong Jiang . Asymmetric Photocatalytic Synthesis of Enantioenriched Azaarene Derivatives[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1609 -1625 . DOI: 10.6023/cjoc202201047
| [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. |
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