镍催化烯烃的不对称还原双官能团化反应研究进展

doi:10.6023/cjoc202205046

摘要/Abstract

烯烃是简单易得的大宗化学品. 烯烃的双官能团化反应可以快速构建复杂的分子, 在有机合成中具有广泛的应用. 与传统烯烃氧化还原中性双官能团化反应相比, 烯烃的还原双官能团化可以向碳碳双键两侧分别引入两个不同的亲电试剂, 具有反应条件温和、官能团耐受性高、无需使用预先制备的有机金属试剂等优点. 综述了镍催化烯烃还原双官能团化反应的最新研究进展, 同时对该类反应的发展前景进行了展望.

关键词: 镍催化, 烯烃, 双官能团化反应, 还原偶联, 立体选择性

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.

Key words: nickel catalysis, alkenes, difunctionalization reaction, reductive cross-coupling; enantioselectivity

引用此文

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.

Yuanyuan Ping, Haixia Song, Wangqing Kong. Recent Advances in Ni-Catalyzed Asymmetric Reductive Difunctionalization of Alkenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3302-3321.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 40

图式1. 过渡金属催化烯烃的双官能团化反应

Scheme 1. Transition metal-catalyzed alkene difunctionalization reactions

图式2. 镍催化烯烃不对称还原环化双官能团化反应

Scheme 2. Ni-catalyzed asymmetric reductive cyclization difunctionalization reactions of alkene

图式3. 镍催化烯烃的双芳基化反应[4]

Scheme 3. Ni-catalyzed diarylation of alkenes

图式4. 机理研究[4]

Scheme 4. Mechanistic studies[4]

图式5. 反应的可能机理[4]

Scheme 5. Proposed mechanism

图式6. 镍催化烯烃的芳基-烯基化反应[5]

Scheme 6. Ni-catalyzed aryl-alkenylation of alkenes

图式7. 镍催化烯烃的芳基-烯基化反应[6]

Scheme 7. Ni-catalyzed aryl-alkenylation of alkenes

图式8. 镍催化烯烃的芳基-单氟烯基化反应[7]

Scheme 8. Ni-catalyzed aryl-fluoroalkenylation of alkenes

图式9. 机理研究[7]

Scheme 9. Mechanistic studies

图式10. 可能的反应机理[7]

Scheme 10. Proposed mechanism

图式11. 镍催化烯烃的芳基-偕二氟烯基化反应[8]

Scheme 11. Ni-catalyzed aryl-difluoroalkenylation of alkenes

图式12. 合成转化[8]

Scheme 12. Synthetic transformations

图式13. 镍催化烯烃的芳基-烯丙基化反应[9]

Scheme 13. Ni-catalyzed aryl-allylation of alkenes

图式14. 镍催化烯烃的芳基-联烯基化反应[10]

Scheme 14. Ni-catalyzed aryl-allenylation of alkenes

图式15. 与炔基溴化物的还原环化[11]

Scheme 15. Reductive cyclization with alkynyl bromides

图式16. 机理研究[11]

Scheme 16. Mechanistic studies

图式17. 可能的反应机理[11]

Scheme 17. Proposed mechanism

图式18. 与非对称炔烃的还原环化[11]

Scheme 18. Reductive cyclization with unsymmetrical alkynes

图式19. 镍催化烯烃的芳基烷基化反应[12]

Scheme 19. Ni-catalyzed aryl-alkylation of alkenes

图式20. 镍催化烯烃的芳基烷基化反应[13]

Scheme 20. Ni-catalyzed aryl-alkylation of alkenes

图式21. 镍催化烯烃的芳基烷基化反应[14]

Scheme 21. Ni-catalyzed aryl-alkylation of alkenes

图式22. 镍催化烯烃的芳基苄基化反应[15]

Scheme 22. Ni-catalyzed aryl-benzylation of alkenes

图式23. 镍催化烯烃的芳基烷基化反应[16]

Scheme 23. Ni-catalyzed aryl-alkylation of alkenes

图式24. 镍催化1,6-二烯的去对称化还原环化反应[17]

Scheme 24. Ni-catalyzed desymmetric reductive cyclization of 1,6-dienes

图式25. 镍催化烯烃的芳基氰基化反应[18]

Scheme 25. Ni-catalyzed aryl-cyanation of alkenes

图式26. 镍催化烯烃的不对称芳基羧基化反应[19]

Scheme 26. Ni-catalyzed carbo-carboxylation of alkenes

图式27. (-)-Debromoflustramine B的合成[19]

Scheme 27. Synthesis of (-)-debromoflustramine B

图式28. (+)-Coixspirolactam A的合成[19]

Scheme 28. Synthesis of (+)-coixspirolactam A

图式29. 镍催化烯烃的不对称芳基羧基化反应[20]

Scheme 29. Ni-catalyzed carbo-carboxylation of alkenes

图式30. 镍催化烯烃的还原芳基酰基化[21]

Scheme 30. Ni-catalyzed aryl-acylation of alkenes

图式31. 镍催化烯烃的芳基氨基化反应[22]

Scheme 31. Ni-catalyzed aryl-amination of alkenes

图式32. 镍催化烯烃的不对称双烯基化反应研究[23]

Scheme 32. Ni-catalyzed divinylation of alkenes

图式33. 光/镍催化烯烃的酰基-烷基化反应[24]

Scheme 33. Nickel and photo dual catalyzed acyl-carbamoylation of alkenes

图式34. 镍催化烯烃酰基-烷基化反应[25]

Scheme 34. Ni-catalyzed acyl-alkylation of alkenes

图式35. 镍催化烯烃的去对称酰基-烷基化反应[26]

Scheme 35. Ni-catalyzed desymmetric acyl-alkylation of alkenes

图式36. 镍催化烯烃的分子间不对称双官能团化反应

Scheme 36. Ni-catalyzed intermolecular reductive difunctionalization of alkenes

图式37. 镍催化苯乙烯不对称还原双芳基化反应[28]

Scheme 37. Ni-catalyzed reductive diarylation of styrenes

图式38. 镍催化烯烃的三组分芳基氟烷基化反应研究[30]

Scheme 38. Ni-catalyzed three-component fluoroalkylarylation of alkenes

图式39. 镍催化烯烃的三组分芳基烷基化反应[31]

Scheme 39. Ni-catalyzed three-component aryl-alkylation of alkenes

图式40. 光/镍协同催化烯烃的三组分芳基烷基化反应[32]

Scheme 40. Nickel and photo dual catalyzed three-component aryl-alkylation of alkenes

参考文献 33

[1]	(a) Dhungana, R. K.; KC, S.; Basnet, P.; Giri, R. Chem. Rec. 2018, 18, 1314. doi: 10.1002/tcr.201700098
	(b) Giri, R.; KC, S. J. Org. Chem. 2018, 83, 3013. doi: 10.1021/acs.joc.7b03128
	(c) Ping, Y.; Li, Y.; Zhu, J.; Kong, W. Angew. Chem. Int. Ed. 2019, 58, 1562. doi: 10.1002/anie.201806088
[2]	(a) Nédélec, J. Y.; Périchon, J.; Troupel, M. Top. Curr. Chem. 1997, 185, 141. pmid: 20047282
	(b) Knappke, C. E. I.; Grupe, S.; Gärtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem.-Eur. J. 2014, 20, 6828. doi: 10.1002/chem.201402302 pmid: 20047282
	(c) Moragas, T.; Correa, A.; Martin, R. Chem.-Eur. J. 2014, 20, 8242. doi: 10.1002/chem.201402509 pmid: 20047282
	(d) Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793. doi: 10.1021/jo500507s pmid: 20047282
	(e) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299. doi: 10.1038/nature13274 pmid: 20047282
	(f) Gu, J.; Wang, X.; Xue, W.; Gong, H. Org. Chem. Front. 2015, 2, 1411. doi: 10.1039/C5QO00224A pmid: 20047282
	(g) Tollefson, E. J.; Hanna, L. E.; Jarvo, E. R. Acc. Chem. Res. 2015, 48, 2344. doi: 10.1021/acs.accounts.5b00223 pmid: 20047282
	(h) Weix, D. J. Acc. Chem. Res. 2015, 48, 1767. doi: 10.1021/acs.accounts.5b00057 pmid: 20047282
	(i) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Chem. Rev. 2015, 115, 9587. doi: 10.1021/acs.chemrev.5b00162 pmid: 20047282
	(j) Wang, X.; Dai, Y.; Gong, H. Top. Curr. Chem. (Z) 2016, 374, 43. doi: 10.1007/s41061-016-0042-2 pmid: 20047282
	(k) Lucas, E. L.; Jarvo, E. R. Nat. Rev. Chem. 2017, 1, 65. doi: 10.1038/s41570-017-0065 pmid: 20047282
	(l) Richmond, E.; Moran, J. Synthesis 2018, 50, 499. doi: 10.1055/s-0036-1591853 pmid: 20047282
	(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. doi: 10.1021/acs.chemrev.1c00383 pmid: 20047282
	(n) Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920. doi: 10.1021/ja9093956 pmid: 20047282
	(o) Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138. doi: 10.1021/ol200617f pmid: 20047282
	(p) Zuo, Z.; Ahneman, D. T.; Chu, L. L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437. pmid: 20047282
	(q) Ping, Y.; Kong, W. Synthesis 2020, 52, 979. doi: 10.1055/s-0039-1690807 pmid: 20047282
	(r) Ping, Y.; Pan, Q.; Guo, Y.; Liu, Y.; Li, X.; Wang, M.; Kong, W. J. Am. Chem. Soc. 2022, 144, 11626. doi: 10.1021/jacs.2c02487 pmid: 20047282
	(s) Ping, Y.; Li, X.; Pan, Q.; Kong, W. Angew. Chem. Int. Ed. 2022, e202201574. pmid: 20047282
[3]	(a) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7442. doi: 10.1021/ja402922w pmid: 25245492
	(b) Cherney, A. H.; Reisman, S. E. J. Am. Chem. Soc. 2014, 136, 14365. doi: 10.1021/ja508067c pmid: 25245492
	(c) Kadunce, N. T.; Reisman, S. E. J. Am. Chem. Soc. 2015, 137, 10480. doi: 10.1021/jacs.5b06466 pmid: 25245492
	(d) Zhao, Y.; Weix, D. J. J. Am. Chem. Soc. 2015, 137, 3237. doi: 10.1021/jacs.5b01909 pmid: 25245492
[4]	(a) Wang, K.; Ding, Z.; Zhou, Z.; Kong, W. J. Am. Chem. Soc. 2018, 140, 12364. doi: 10.1021/jacs.8b08190
	(b) Wang, K.; Kong, W. Synlett 2019, 30, 1008. doi: 10.1055/s-0037-1612214
	(c) Ju, B.; Chen, S.; Kong, W. Chem. Commun. 2019, 55, 14311. doi: 10.1039/C9CC07036B
	(d) Li, Y.; Wang, K.; Ping, Y.; Wang, Y.; Kong, W. Org. Lett. 2018, 20, 921. doi: 10.1021/acs.orglett.7b03713
[5]	(a) Li, Y.; Ding, Z.; Lei, A.; Kong, W. Org. Chem. Front. 2019, 6, 3305. doi: 10.1039/C9QO00744J
	(b) Ju, B.; Chen, S.; Kong, W. Org. Lett. 2019, 21, 9343. doi: 10.1021/acs.orglett.9b03517
	(c) Xu, S.; Wang, K.; Kong, W. Org. Lett. 2019, 21, 7498. doi: 10.1021/acs.orglett.9b02788
[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. doi: 10.1021/jacs.9b03863
[7]	Ma, T.; Chen, Y.; Li, Y.; Ping, Y.; Kong, W. ACS Catal. 2019, 9, 9127. doi: 10.1021/acscatal.9b03172
[8]	Pan, Q.; Ping, Y.; Wang, Y.; Guo, Y.; Kong, W. J. Am. Chem. Soc. 2021, 143, 10282. doi: 10.1021/jacs.1c03827 pmid: 34162201
[9]	Lin, Z.; Jin, Y.; Hu, W.; Wang, C. Chem. Sci. 2021, 12, 6712. doi: 10.1039/D1SC01115D
[10]	Jin, Y.; Wen, H.; Yang, F.; Ding, D.; Wang, C. ACS Catal. 2021, 11, 13355. doi: 10.1021/acscatal.1c04143
[11]	Ping, Y.; Wang, K.; Pan, Q.; Ding, Z.; Zhou, Z.; Guo, Y.; Kong, W. ACS Catal. 2019, 9, 7335. doi: 10.1021/acscatal.9b02081
[12]	Qin, X.; Lee, M.; Zhou, J. Angew. Chem. Int. Ed. 2017, 56, 12723. doi: 10.1002/anie.201707134
[13]	(a) Jin, Y.; Wang, C. Chem. Sci. 2019, 10, 1780. doi: 10.1039/C8SC04279A
	(b) Jin, Y.; Wang, C. Angew. Chem. Int. Ed. 2019, 58, 6722. doi: 10.1002/anie.201901067
[14]	Jin, Y.; Yang, H.; Wang, C. Org. Lett. 2019, 21, 7602. doi: 10.1021/acs.orglett.9b02870
[15]	Jin, Y.; Yang, H.; Wang, C. Org. Lett. 2020, 22, 2724. doi: 10.1021/acs.orglett.0c00688
[16]	Fang, K.; Huang, W.; Shan, C.; Qu, J.; Chen, Y. Org. Lett. 2021, 23, 5523. doi: 10.1021/acs.orglett.1c01871
[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. doi: 10.1021/acs.orglett.1c02270
[19]	Chen, X.; Yue, J.; Gui, Y.; Liu, J.; Ran, C.; Kong, W.; Zhou, W.; Yu, D. Angew. Chem. Int. Ed. 2021, 60, 14068. doi: 10.1002/anie.202102769
[20]	Cerveri, A.; Giovanelli, R.; Sella, D.; Pedrazzani, R.; Monari, M.; Nieto Faza, O.; López, C.; Bandini, M. Chem.-Eur. J. 2021, 27, 7657. doi: 10.1002/chem.202101082 pmid: 33829576
[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. doi: 10.1002/anie.201913743
[23]	Qiao, J.; Zhang, Y.; Yao, Q.; Zhao, Z.; Peng, X.; Shu, X. J. Am. Chem. Soc. 2021, 143, 12961. doi: 10.1021/jacs.1c05670
[24]	Fan, P.; Lan, Y.; Zhang, C.; Wang, C. J. Am. Chem. Soc. 2021, 142, 2180. doi: 10.1021/jacs.9b12554
[25]	Wu, X.; Qu, J.; Chen, Y. J. Am. Chem. Soc. 2020, 142, 15654. doi: 10.1021/jacs.0c07126
[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. doi: 10.1021/jacs.9b10026
[28]	Anthony, D.; Lin, Q.; Baudet, J.; Diao, T. Angew. Chem. Int. Ed. 2019, 58, 3198. doi: 10.1002/anie.201900228 pmid: 30681765
[29]	Zhao, X.; Tu, H.; Guo, L.; Zhu, S.; Qing, F.; Chu, L. Nat. Commun. 2018, 9, 3488. doi: 10.1038/s41467-018-05951-6
[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. doi: 10.1021/jacs.0c03708
[31]	Wei, X.; Shu, W.; Andrés, G. D.; Estíbaliz, M.; Cristina, N. J. Am. Chem. Soc. 2020, 142, 13515. doi: 10.1021/jacs.0c05254
[32]	Qian, P.; Guan, H.; Wang, Y.; Lu, Q.; Zhang, F.; Xiong, D.; Walsh, P.; Mao, J. Nat. Commun. 2021, 12, 6613. doi: 10.1038/s41467-021-26794-8
[33]	Li, J.; Luo, Y.; Cheo, H.; Lan, Y.; Wu, J. Chem 2019, 5, 192. doi: 10.1016/j.chempr.2018.10.006