镍催化烯烃的不对称还原双官能团化反应研究进展
收稿日期: 2022-05-24
修回日期: 2022-06-27
网络出版日期: 2022-07-05
基金资助
国家自然科学基金(22171215); 中央高校基本科研业务费专项资金(2042021kf0032); 中国博士后面上基金(2020M680108); 湖北省博士后基金(211000012)
Recent Advances in Ni-Catalyzed Asymmetric Reductive Difunctionalization of Alkenes
Received date: 2022-05-24
Revised date: 2022-06-27
Online published: 2022-07-05
Supported by
National Natural Science Foundation of China(22171215); Fundamental Research Funds for the Central Universities(2042021kf0032); China Postdoctoral Science Foundation(2020M680108); Postdoctoral Foundation of Hubei Province(211000012)
平媛媛 , 宋海霞 , 孔望清 . 镍催化烯烃的不对称还原双官能团化反应研究进展[J]. 有机化学, 2022 , 42(10) : 3302 -3321 . DOI: 10.6023/cjoc202205046
Alkenes are cheap and easily available bulk industrial feedstocks. Difunctionalization of alkenes can rapidly construct complex molecules, which have broad applications in organic synthesis. Compared with traditional redox-neutral alkene difunctionalization, the reductive difunctionalization of alkenes can introduce two different electrophiles to both sides of the carbon-carbon double bond, which has the advantages of mild reaction conditions, high functional group tolerance, and no need for pre-prepared organometallic reagents. The latest research progress in nickel-catalyzed reductive difunctionalization of alkenes is summarized. The development prospect of the reaction is prospected.
| [1] | (a) Dhungana, R. K.; KC, S.; Basnet, P.; Giri, R. Chem. Rec. 2018, 18, 1314. |
| [1] | (b) Giri, R.; KC, S. J. Org. Chem. 2018, 83, 3013. |
| [1] | (c) Ping, Y.; Li, Y.; Zhu, J.; Kong, W. Angew. Chem. Int. Ed. 2019, 58, 1562. |
| [2] | (a) Nédélec, J. Y.; Périchon, J.; Troupel, M. Top. Curr. Chem. 1997, 185, 141. |
| [2] | (b) Knappke, C. E. I.; Grupe, S.; Gärtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem.-Eur. J. 2014, 20, 6828. |
| [2] | (c) Moragas, T.; Correa, A.; Martin, R. Chem.-Eur. J. 2014, 20, 8242. |
| [2] | (d) Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793. |
| [2] | (e) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299. |
| [2] | (f) Gu, J.; Wang, X.; Xue, W.; Gong, H. Org. Chem. Front. 2015, 2, 1411. |
| [2] | (g) Tollefson, E. J.; Hanna, L. E.; Jarvo, E. R. Acc. Chem. Res. 2015, 48, 2344. |
| [2] | (h) Weix, D. J. Acc. Chem. Res. 2015, 48, 1767. |
| [2] | (i) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Chem. Rev. 2015, 115, 9587. |
| [2] | (j) Wang, X.; Dai, Y.; Gong, H. Top. Curr. Chem. (Z) 2016, 374, 43. |
| [2] | (k) Lucas, E. L.; Jarvo, E. R. Nat. Rev. Chem. 2017, 1, 65. |
| [2] | (l) Richmond, E.; Moran, J. Synthesis 2018, 50, 499. |
| [2] | (m) Amy, Y. C.; Ian, B. P.; Noah, B. B.; Benito, F. B.; Grant, A. E.; Lucas, I. F.; Olivia, L. G.; Marissa, N. L.; Beryl, X. L.; Yu, F. L.; Edna, M.; Agustin, M.; James, V. O.; Nicholas, L. R.; Holt, A. S.; Ciaran, P. S.; MacMillan, D. W. C. Chem. Rev. 2022, 122, 1485. |
| [2] | (n) Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920. |
| [2] | (o) Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138. |
| [2] | (p) Zuo, Z.; Ahneman, D. T.; Chu, L. L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437. |
| [2] | (q) Ping, Y.; Kong, W. Synthesis 2020, 52, 979. |
| [2] | (r) Ping, Y.; Pan, Q.; Guo, Y.; Liu, Y.; Li, X.; Wang, M.; Kong, W. J. Am. Chem. Soc. 2022, 144, 11626. |
| [2] | (s) Ping, Y.; Li, X.; Pan, Q.; Kong, W. Angew. Chem. Int. Ed. 2022, e202201574. |
| [3] | (a) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442. |
| [3] | (b) Cherney, A. H.; Reisman, S. E. J. Am. Chem. Soc. 2014, 136, 14365. |
| [3] | (c) Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2015, 137, 10480. |
| [3] | (d) Zhao, Y.; Weix, D. J. J. Am. Chem. Soc. 2015, 137, 3237. |
| [4] | (a) Wang, K.; Ding, Z.; Zhou, Z.; Kong, W. J. Am. Chem. Soc. 2018, 140, 12364. |
| [4] | (b) Wang, K.; Kong, W. Synlett 2019, 30, 1008. |
| [4] | (c) Ju, B.; Chen, S.; Kong, W. Chem. Commun. 2019, 55, 14311. |
| [4] | (d) Li, Y.; Wang, K.; Ping, Y.; Wang, Y.; Kong, W. Org. Lett. 2018, 20, 921. |
| [5] | (a) Li, Y.; Ding, Z.; Lei, A.; Kong, W. Org. Chem. Front. 2019, 6, 3305. |
| [5] | (b) Ju, B.; Chen, S.; Kong, W. Org. Lett. 2019, 21, 9343. |
| [5] | (c) Xu, S.; Wang, K.; Kong, W. Org. Lett. 2019, 21, 7498. |
| [6] | Tian, Z.; Qiao, J.; Xu, G.; Pang, X.; Qi, L.; Ma, W.; Zhao, Z.; Duan, J.; Du, Y.; Su, P.; Liu, X.; Shu, X. J. Am. Chem. Soc. 2019, 141, 7637. |
| [7] | Ma, T.; Chen, Y.; Li, Y.; Ping, Y.; Kong, W. ACS Catal. 2019, 9, 9127. |
| [8] | Pan, Q.; Ping, Y.; Wang, Y.; Guo, Y.; Kong, W. J. Am. Chem. Soc. 2021, 143, 10282. |
| [9] | Lin, Z.; Jin, Y.; Hu, W.; Wang, C. Chem. Sci. 2021, 12, 6712. |
| [10] | Jin, Y.; Wen, H.; Yang, F.; Ding, D.; Wang, C. ACS Catal. 2021, 11, 13355. |
| [11] | Ping, Y.; Wang, K.; Pan, Q.; Ding, Z.; Zhou, Z.; Guo, Y.; Kong, W. ACS Catal. 2019, 9, 7335. |
| [12] | Qin, X.; Lee, M.; Zhou, J. Angew. Chem. Int. Ed. 2017, 56, 12723. |
| [13] | (a) Jin, Y.; Wang, C. Chem. Sci. 2019, 10, 1780. |
| [13] | (b) Jin, Y.; Wang, C. Angew. Chem. Int. Ed. 2019, 58, 6722. |
| [14] | Jin, Y.; Yang, H.; Wang, C. Org. Lett. 2019, 21, 7602. |
| [15] | Jin, Y.; Yang, H.; Wang, C. Org. Lett. 2020, 22, 2724. |
| [16] | Fang, K.; Huang, W.; Shan, C.; Qu, J.; Chen, Y. Org. Lett. 2021, 23, 5523. |
| [17] | Zhao, T.; Li, J.; Qi, L. Angew. Chem. Int. Ed. 2022, 61, e202115702. |
| [18] | Li, H.; Chen, J.; Dong, J.; Kong, W. Org. Lett. 2021, 23, 6466. |
| [19] | Chen, X.; Yue, J.; Gui, Y.; Liu, J.; Ran, C.; Kong, W.; Zhou, W.; Yu, D. Angew. Chem. Int. Ed. 2021, 60, 14068. |
| [20] | Cerveri, A.; Giovanelli, R.; Sella, D.; Pedrazzani, R.; Monari, M.; Nieto Faza, O.; López, C.; Bandini, M. Chem.-Eur. J. 2021, 27, 7657. |
| [21] | Jin, Y.; Fan, P.; Wang, C. CCS Chem. 2021, 3, 1780. |
| [22] | He, J.; Xue, Y.; Han, B.; Zhang, C.; Wang, Y.; Zhu, S. Angew. Chem. Int. Ed. 2019, 59, 2328. |
| [23] | Qiao, J.; Zhang, Y.; Yao, Q.; Zhao, Z.; Peng, X.; Shu, X. J. Am. Chem. Soc. 2021, 143, 12961. |
| [24] | Fan, P.; Lan, Y.; Zhang, C.; Wang, C. J. Am. Chem. Soc. 2021, 142, 2180. |
| [25] | Wu, X.; Qu, J.; Chen, Y. J. Am. Chem. Soc. 2020, 142, 15654. |
| [26] | Wu, X.; Luan, B.; Zhao, W.; He, F.; Wu, X. Y.; Qu, J.; Chen, Y. Angew. Chem. Int. Ed. 2022, 61, e202111598. |
| [27] | Lin, Q.; Diao, T. J. Am. Chem. Soc. 2019, 141, 17937. |
| [28] | Anthony, D.; Lin, Q.; Baudet, J.; Diao, T. Angew. Chem. Int. Ed. 2019, 58, 3198. |
| [29] | Zhao, X.; Tu, H.; Guo, L.; Zhu, S.; Qing, F.; Chu, L. Nat. Commun. 2018, 9, 3488. |
| [30] | Tu, H.; Wang, F.; Huo, L.; Li, Y.; Zhu, S.; Zhao, X.; Li, H.; Qing, F.; Chu, L. J. Am. Chem. Soc. 2020, 142, 9604. |
| [31] | Wei, X.; Shu, W.; Andrés, G. D.; Estíbaliz, M.; Cristina, N. J. Am. Chem. Soc. 2020, 142, 13515. |
| [32] | Qian, P.; Guan, H.; Wang, Y.; Lu, Q.; Zhang, F.; Xiong, D.; Walsh, P.; Mao, J. Nat. Commun. 2021, 12, 6613. |
| [33] | Li, J.; Luo, Y.; Cheo, H.; Lan, Y.; Wu, J. Chem 2019, 5, 192. |
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