Chinese Journal of Organic Chemistry >
Recent Advances of Efficient Synthesis of Chiral Molecules Promoted by Pd/Chiral Phosphoric Acid Synergistic Catalysis
Received date: 2022-11-30
Revised date: 2023-02-16
Online published: 2023-03-01
Supported by
National Natural Science Foundation of China(22071187); National Natural Science Foundation of China(22271226); Natural Science Foundation of Hubei Province(2020CFA036); Natural Science Foundation of Hubei Province(2021CFA069); National Youth Talent Support Program
Transition metal palladium-catalyzed asymmetric reaction is an important and efficient method to synthesize chiral compounds. It has made considerable progress and achieved great success in the past decades. However, some reactions could not achieve high reactivity and excellent stereoselectivity just promoted by transition metal palladium catalysis. Therefore, it is of great significance to combine transition metal palladium catalysis and organocatalysis, which could be conducive to dissolve these challenging problems and received great attention. In recent years, a variety of asymmetric catalytic reactions have been efficiently realized by the synergistic catalysis system of transition metal palladium catalysis and chiral phosphoric acids with high chemo-, regio-, and stereoselectivity, and considerable research results and some important breakthroughs have been achieved. The recent progress of asymmetric allylation reaction, C(sp3)—H, C(sp2)—H functionalization and other reactions promoted by this synergistic catalysis system is summarized, the interaction between catalysts and substrates is systematically analyzed, and the influence factors of reactivity and selectivity are deeply discussed.
Xun Xiang , Zhaolin He , Xiuqin Dong . Recent Advances of Efficient Synthesis of Chiral Molecules Promoted by Pd/Chiral Phosphoric Acid Synergistic Catalysis[J]. Chinese Journal of Organic Chemistry, 2023 , 43(3) : 791 -808 . DOI: 10.6023/cjoc202211043
| [1] | (a) Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337. |
| [1] | (b) Chen, D.-F.; Han, Z.-Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365. |
| [1] | (c) Afewerki, S.; Córdova, A. Chem. Rev. 2016, 116, 13512. |
| [1] | (d) Mahlau, M.; List, B. Angew. Chem., Int. Ed. 2013, 52, 518. |
| [1] | (e) Wu, X., Li, M.; Gong, L.-Z. Acta Chim. Sin. 2013, 71, 1091. |
| [1] | (f) Han, Z.-Y.; Gong, L.-Z. Prog. Chem. 2018, 30, 505. |
| [1] | (g) Wang, P.-S.; Chen, D.-F.; Gong, L.-Z. Top. Curr. Chem. 2020, 378, 9. |
| [2] | (a) Li, X.; Song, Q. Chin. Chem. Lett. 2018, 29, 1181. |
| [2] | (b) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156. |
| [2] | (c) Liu, W.; Yang, X. Asian J. Org. Chem. 2021, 10, 692. |
| [2] | (d) Lv, J.; Luo, S. Chem. Commun. 2013, 49, 847. |
| [2] | (e) Maji, R.; Mallojjala, S. C.; Wheeler, S. E. Chem. Soc. Rev. 2018, 47, 1142. |
| [2] | (f) Xia, Z.-L.; Xuxu, Q.-F.; Zheng, C.; You, S.-L. Chem. Soc. Rev. 2020, 49, 286. |
| [2] | (g) Rahman, A.; Lin, X. Org. Biomol. Chem. 2018, 16, 4753. |
| [2] | (h) Wu, H.; He, Y.-P.; Shi, F. Synthesis 2015, 47, 1990. |
| [3] | (a) Wang, P.-S.; Gong, L.-Z. Acc. Chem. Res. 2020, 53, 2841. |
| [3] | (b) Wang, P.-S.; Gong, L.-Z. Synthesis 2022, 54, 4795. |
| [4] | (a) Godleski, S. A. In Comprehensive Organic Synthesis, Eds.: Trost, B. M.; Fleming, I., Pergamon Press, New York, 1991. |
| [4] | (b) Tsuji, J. Transition Metal Reagents and Catalysts, Wiley, New York, 2000. |
| [4] | (c) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921. |
| [4] | (d) Weaver, J. D.; Recio III, A.; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846. |
| [5] | Santanu, M.; List, B. J. Am. Chem. Soc. 2007, 129, 11336. |
| [6] | Reetz, M. T.; Westermann, J.; Kyung, S.-H. Chem. Ber. 1985, 118, 1050. |
| [7] | Jiang, G.; List, B. Angew. Chem., Int. Ed. 2011, 50, 9471. |
| [8] | Tao, Z.-L.; Zhang, W.-Q.; Chen, D.-F.; Adele, A.; Gong, L-Z. J. Am. Chem. Soc. 2013, 135, 9255. |
| [9] | Banerjee, D.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2014, 53, 13049. |
| [10] | Pupo, G.; Properzi, R.; List, B. Angew. Chem., Int. Ed. 2016, 55, 6099. |
| [11] | Kang, Z.-K.; Chang, W.-J.; Tian, X.; Fu, X.; Zhao, W.-X.; Xu, X.-F.; Liang, Y.; Hu, W.-H. J. Am. Chem. Soc. 2021, 143, 20818. |
| [12] | (a) Chai, Z.; Rainey, T. J. J. Am. Chem. Soc. 2012, 134, 3615. |
| [12] | (b) Jindal, G.; Sunoj, R. B. J. Am. Chem. Soc. 2014, 136, 15998. |
| [13] | Yan, S.-B.; Zhang, S.; Duan, W.-L. Org. Lett. 2015, 17, 2458. |
| [14] | Tao, Z.-L.; Li, X.-H.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2015, 137, 4054. |
| [15] | Li, L.-L.; Tao, Z.-L.; Han, Z.-Y.; Gong, L.-Z. Org. Lett. 2017, 19, 102. |
| [16] | Lin, H.-C.; Wang, P.-S.; Tao, Z.-L.; Chen, Y.-G.; Han, Z.-Y.; Gong, L.-Z. J. Am. Chem. Soc. 2016, 138, 14354. |
| [17] | (a) Wang, P.-S.; Lin, H.-C.; Zhai, Y.-J.; Han, Z.-Y.; Gong, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 12218. |
| [17] | (b) Fan, L.-F.; Wang, P.-S.; Gong, L.-Z. Org. Lett. 2019, 21, 6720. |
| [18] | Wang, H.; Tong, H.-R.; He, G.; Chen, G. Angew. Chem., Int. Ed. 2016, 55, 15387. |
| [19] | SmalleyOrcid, A. P.; Cuthbertson, J. D.; Gaunt, M, J. J. Am. Chem. Soc. 2017, 139, 1412. |
| [20] | Yang, L.; Melot, R.; Neuburger, M.; Baudoin, O. Chem. Sci. 2017, 8, 1344. |
| [21] | Jain, P.; Verma, P.; Xia, G.-Q.; Yu, J.-Q. Nat. Chem. 2017, 9, 140. |
| [22] | Zhou, X.-L.; Su, Y.-L.; Wang, P.-S.; Gong, L.-Z. Acta Chim. Sinica 2018, 76, 857. (in Chinese) |
| [22] | (周霄乐, 苏永亮, 汪普生, 龚流柱, 化学学报, 2018, 76, 857.) |
| [23] | Yan, S.-Y.; Han, Y.-Q.; Yao, Q.-J.; Nie, X.-L.; Liu, L.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 9093. |
| [24] | Jiang, H.-J.; Zhong, X.-M.; Liu, Z.-Y.; Geng, R.-L.; Li, Y.-Y.; Wu, Y.-D.; Zhang, X.-H.; Gong, L.-Z. Angew. Chem., Int. Ed. 2020, 59, 12774. |
| [25] | Kurata, H.; Kusumi, K.; Otsuki, K; Suzuki, R.; Kurono, M.; Tokuda, N.; Takada, Y.; Shioya, H.; Mizuno, H.; Komiya, T.; Ono, T.; Hagiya, H.; Minami, M.; Nakade, S.; Habashita, H. Bioorg. Med. Chem. Lett. 2012, 22, 144. |
| [26] | Han, Y.-Q.; Zhang, Q.; Yang, X.; Jiang, M.-X.; Ding, Y.; Shi, B.-F. Org. Lett. 2021, 23, 97. |
| [27] | Zhang, S.; Lu, J.; Ye, J.; Duan, W.-L. Chin. J. Org. Chem. 2016, 36, 752. (in Chinese) |
| [27] | (张松, 陆俊筑, 叶金星, 段伟良, 有机化学, 2016, 36, 752.) |
| [28] | Li, Z.; Lin, Z.-Q.; Yan, C.-G.; Duan, W.-L. Organometallics 2019, 38, 3916. |
| [29] | Luo, J.; Zhang, T.; Wang, L.; Liao, G.; Yao, Q.-J.; Wu, Y.-J.; Zhan, B.-B.; Lan, Y.; Lin, X.-F.; Shi, B.-F. Angew. Chem., Int. Ed. 2019, 58, 6708. |
| [30] | Zhan, B.-B.; Jia, Z.-S.; Luo, J.; Jin, L.; Lin, X.-F.; Shi, B.-F. Org. Lett. 2020, 22, 9693. |
| [31] | Zhan, B.-B.; Wang, L.; Luo, J.; Lin, X.-F.; Shi, B.-F. Angew. Chem., Int. Ed. 2020, 59, 3568. |
| [32] | Jin, L.; Zhang, P.; Li, Y.; Yu, X.; Shi, B.-F. J. Am. Chem. Soc. 2021, 143, 12335. |
| [33] | Liao, G.; Zhang, T.; Jin, L.; Wang, B.-J.; Xu, C.-K.; Lan, Y.; Zhao, Y.; Shi, B.-F. Angew. Chem., Int. Ed. 2022, 61, e202115221. |
| [34] | Yu, S.-Y.; Zhang, H.; Gao, Y.; Mo, L.; Wang, S.; Yao, Z.-J. J. Am. Chem. Soc. 2013, 135, 11402. |
| [35] | Nelson, H. M.; Williams, B. D.; Miro, J.; Toste, F. D. J. Am. Chem. Soc. 2015, 137, 3213. |
| [36] | Yamamoto, E.; Hilton, M. J.; Orlandi, M.; Saini, V.; Toste, F. D.; Sigman, M. S. J. Am. Chem. Soc. 2016, 138, 15877. |
| [37] | Avila, C. M.; Patel, J. S.; Reddi, Y.; Saito, M.; Nelson, H. M.; Shunatona, H. P.; Sigman, M. S.; Sunoj, R. B.; Toste, F. D. Angew. Chem., Int. Ed. 2017, 56, 5806. |
| [38] | Reddi, Y.; Tsai, C. C.; Avila, C. M.; Toste, F. D.; Sunoj, R. B. J. Am. Chem. Soc. 2019, 141, 998. |
| [39] | Nimmagadda, S. K.; Liu, M.-Y.; Karunananda, M. K.; Gao, D.-W.; Apolinar, O.; Chen, J. S.; Liu, P.; Engle, K. M. Angew. Chem., Int. Ed. 2019, 58, 3923. |
/
| 〈 |
|
〉 |
