Chinese Journal of Organic Chemistry >
Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids
Received date: 2022-05-19
Revised date: 2022-06-25
Online published: 2022-07-05
Supported by
National Natural Science Foundation of China(22071209); National Natural Science Foundation of China(22071206); National Youth Talent Support Program
In recent years, visible-light photocatalytic asymmetric synthesis has shown considerable potential in the mild and rapid construction of optically active organic molecules with structural diversity. Chiral Lewis acids (CLA), including chiral borane compounds, lanthanum complexes, first-row transition metal complexes, and chiral-at-iridium or rhodium complexes, have been established as one class of the most effective catalysts being capable of controlling the stereochemistry in photo-induced chemical transformations. The recent advances in this emerging field were presented by classifying the reactions into bifunctional CLA photocatalytic reactions and reactions enabled by dual catalysis with a CLA catalyst and an external photosensitizer, expecting that these studies will stimulate progress in organic synthesis, photocatalysis and asymmetric catalysis.
Xiuliang Cheng , Dong Li , Boxuan Yang , Yumei Lin , Lei Gong . Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3335 -3350 . DOI: 10.6023/cjoc202205032
| [1] | Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322. |
| [2] | Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527. |
| [3] | Zhang, H.-T.; Gu, L.-J.; Huang, X.-Z.; Wang, R.; Jin, C.; Li, G.-P. Chin. Chem. Lett. 2016, 27, 256. |
| [4] | Qu, Z.; Wang, P.; Chen, X.; Deng, G.-J.; Huang, H. Chin. Chem. Lett. 2021, 32, 2582. |
| [5] | Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Soc. Rev. 2016, 45, 2044. |
| [6] | Poplata, S.; Troster, A.; Zou, Y. Q.; Bach, T. Chem. Rev. 2016, 116, 9748. |
| [7] | Zhou, Q. Q.; Zou, Y. Q.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2019, 58, 1586. |
| [8] | Lipp, A.; Badir, S. O.; Molander, G. A. Angew. Chem., Int. Ed. 2021, 60, 1714. |
| [9] | Wang, C.; Lu, Z. Org. Chem. Front. 2015, 2, 179. |
| [10] | Meggers, E. Angew. Chem., Int. Ed. 2017, 56, 5668. |
| [11] | Vega-Peñaloza, A.; Paria, S.; Bonchio, M.; Dell’Amico, L.; Companyó, X. ACS Catal. 2019, 9, 6058. |
| [12] | Jiang, C.; Chen, W.; Zheng, W. H.; Lu, H. Org. Biomol. Chem. 2019, 17, 8673. |
| [13] | Schwinger, D. P.; Bach, T. Acc. Chem. Res. 2020, 53, 1933. |
| [14] | Li, S.; Xiang, S. H.; Tan, B. Chin. J. Chem. 2020, 38, 213. |
| [15] | Wang, A.-E.; Huang, P.-Q. Sci. China: Chem. 2020, 63, 871. |
| [16] | Santelli, M.; Pons, J. M. Lewis Acids and Selectivity in Organic Synthesis, CRC Press, Boca Raton, 1996. |
| [17] | Fukuzumi, S.; Jung, J.; Lee, Y. M.; Nam, W. Asian J. Org. Chem. 2017, 6, 397. |
| [18] | Yoon, T. P. Acc. Chem. Res. 2016, 49, 2307. |
| [19] | Brimioulle, R.; Lenhart, D.; Maturi, M. M.; Bach, T. Angew. Chem., Int. Ed. 2015, 54, 3872. |
| [20] | Hong, B. C. Org. Biomol. Chem. 2020, 18, 4298. |
| [21] | Yang, K.; Song, Q. Acc. Chem. Res. 2021, 54, 2298. |
| [22] | Lewis, F. D.; Howard, D. K.; Oxman, J. D. J. Am. Chem. Soc. 1983, 105, 3344. |
| [23] | Stegbauer, S.; Jandl, C.; Bach, T. Angew. Chem., Int. Ed. 2018, 57, 14593. |
| [24] | Leverenz, M.; Merten, C.; Dreuw, A.; Bach, T. J. Am. Chem. Soc. 2019, 141, 20053. |
| [25] | Miyasaka, H. Acc. Chem. Res. 2013, 46, 248. |
| [26] | Crisenza, G. E. M.; Mazzarella, D.; Melchiorre, P. J. Am. Chem. Soc. 2020, 142, 5461. |
| [27] | Kim, J. Y.; Lee, Y. S.; Ryu, D. H. ACS Catal. 2021, 11, 14811. |
| [28] | Gong, L.; Wenzel, M.; Meggers, E. Acc. Chem. Res. 2013, 46, 2635. |
| [29] | Huang, X.; Meggers, E. Acc. Chem. Res. 2019, 52, 833. |
| [30] | Huo, H.; Shen, X.; Wang, C.; Zhang, L.; Rose, P.; Chen, L. A.; Harms, K.; Marsch, M.; Hilt, G.; Meggers, E. Nature 2014, 515, 100. |
| [31] | Huo, H.; Wang, C.; Harms, K.; Meggers, E. J. Am. Chem. Soc. 2015, 137, 9551. |
| [32] | Wang, C.; Qin, J.; Shen, X.; Riedel, R.; Harms, K.; Meggers, E. Angew. Chem., Int. Ed. 2016, 55, 685. |
| [33] | Tan, Y.; Yuan, W.; Gong, L.; Meggers, E. Angew. Chem., Int. Ed. 2015, 54, 13045. |
| [34] | Shen, X.; Harms, K.; Marsch, M.; Meggers, E. Chem.-Eur. J. 2016, 22, 9102. |
| [35] | Steinlandt, P. S.; Zuo, W.; Harms, K.; Meggers, E. Chem.- Eur. J. 2019, 25, 15333. |
| [36] | Zhang, C.; Gao, A. Z.; Nie, X.; Ye, C. X.; Ivlev, S. I.; Chen, S.; Meggers, E. J. Am. Chem. Soc. 2021, 143, 13393. |
| [37] | Yoon, T. P. ACS Catal. 2013, 3, 895. |
| [38] | Huang, X.; Quinn, T. R.; Harms, K.; Webster, R. D.; Zhang, L.; Wiest, O.; Meggers, E. J. Am. Chem. Soc. 2017, 139, 9120. |
| [39] | Huang, X.; Li, X.; Xie, X.; Harms, K.; Riedel, R.; Meggers, E. Nat. Commun. 2017, 8, 2245. |
| [40] | Hu, N.; Jung, H.; Zheng, Y.; Lee, J.; Zhang, L.; Ullah, Z.; Xie, X.; Harms, K.; Baik, M. H.; Meggers, E. Angew. Chem., Int. Ed. 2018, 57, 6242. |
| [41] | Dai, X.; Li, Y.; Zhang, S.; Gong, L. Chin. J. Org. Chem. 2019, 39, 1711. (in Chinese). |
| [41] | (代雪梅, 李延军, 张少南, 龚磊, 有机化学, 2019, 39, 1711.) |
| [42] | Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299. |
| [43] | Zhang, S.; Cao, S.; Lin, Y.-M.; Sha, L.; Lu, C.; Gong, L. Chin. J. Catal. 2022, 43, 564. |
| [44] | Tellis John, C.; Primer David, N.; Molander Gary, A. Science 2014, 345, 433. |
| [45] | Ding, W.; Lu, L. Q.; Zhou, Q. Q.; Wei, Y.; Chen, J. R.; Xiao, W. J. J. Am. Chem. Soc. 2017, 139, 63. |
| [46] | Shen, X.; Li, Y.; Wen, Z.; Cao, S.; Hou, X.; Gong, L. Chem. Sci. 2018, 9, 4562. |
| [47] | Cao, S.; Ye, Z.; Chen, Y.; Lin, Y.-M.; Fang, J.; Wang, Y.; Yang, B.; Gong, L. CCS Chem. 2021, 3, 3329. |
| [48] | Li, Y.; Zhou, K.; Wen, Z.; Cao, S.; Shen, X.; Lei, M.; Gong, L. J. Am. Chem. Soc. 2018, 140, 15850. |
| [49] | Han, B.; Li, Y.; Yu, Y.; Gong, L. Nat. Commun. 2019, 10, 3804. |
| [50] | Zhou, K.; Yu, Y.; Lin, Y.-M.; Li, Y.; Gong, L. Green Chem. 2020, 22, 4597. |
| [51] | Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035. |
| [52] | Du, J.; Skubi Kazimer, L.; Schultz Danielle, M.; Yoon Tehshik, P. Science 2014, 344, 392. |
| [53] | Ruiz Espelt, L.; McPherson, I. S.; Wiensch, E. M.; Yoon, T. P. J. Am. Chem. Soc. 2015, 137, 2452. |
| [54] | Dong, X.; Li, Q. Y.; Yoon, T. P. Org. Lett. 2021, 23, 5703. |
| [55] | Amador, A. G.; Sherbrook, E. M.; Yoon, T. P. J. Am. Chem. Soc. 2016, 138, 4722. |
| [56] | Huang, X.; Webster, R. D.; Harms, K.; Meggers, E. J. Am. Chem. Soc. 2016, 138, 12636. |
| [57] | Huo, H.; Harms, K.; Meggers, E. J. Am. Chem. Soc. 2016, 138, 6936. |
| [58] | Wang, C.; Harms, K.; Meggers, E. Angew. Chem., Int. Ed. 2016, 55, 13495. |
| [59] | Zhou, Z.; Li, Y.; Han, B.; Gong, L.; Meggers, E. Chem. Sci. 2017, 8, 5757. |
| [60] | Ma, J.; Xie, X.; Meggers, E. Chem.-Eur. J. 2018, 24, 259. |
| [61] | Liang, H.; Xu, G. Q.; Feng, Z. T.; Wang, Z. Y.; Xu, P. F. J. Org. Chem. 2019, 84, 60. |
| [62] | Liu, J.; Ding, W.; Zhou, Q. Q.; Liu, D.; Lu, L. Q.; Xiao, W. J. Org. Lett. 2018, 20, 461. |
| [63] | Ye, C. X.; Melcamu, Y. Y.; Li, H. H.; Cheng, J. T.; Zhang, T. T.; Ruan, Y. P.; Zheng, X.; Lu, X.; Huang, P. Q. Nat. Commun. 2018, 9, 410. |
| [64] | Zhang, K.; Lu, L. Q.; Jia, Y.; Wang, Y.; Lu, F. D.; Pan, F.; Xiao, W. J. Angew. Chem., Int. Ed. 2019, 58, 13375. |
| [65] | Pagire, S. K.; Kumagai, N.; Shibasaki, M. Chem. Sci. 2020, 11, 5168. |
| [66] | Labinger, J.; Bercaw, J. Nature 2002, 417, 507. |
| [67] | Goldberg, K. I.; Goldman, A. S. Acc. Chem. Res. 2017, 50, 620. |
| [68] | Davies, H. M. L.; Liao, K. Nat. Rev. Chem. 2019, 3, 347. |
| [69] | Li, Y.; Lei, M.; Gong, L. Nat. Catal. 2019, 2, 1016. |
| [70] | Cao, S.; Hong, W.; Ye, Z.; Gong, L. Nat. Commun. 2021, 12, 2377. |
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