Recent Advances in Ni-Catalyzed Asymmetric Reductive Difunctionalization of Alkenes

doi:10.6023/cjoc202205046

Abstract

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

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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.

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Fig. & Tab. 40

Scheme 1. Transition metal-catalyzed alkene difunctionalization reactions

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

Scheme 3. Ni-catalyzed diarylation of alkenes

Scheme 4. Mechanistic studies[4]

Scheme 5. Proposed mechanism

Scheme 6. Ni-catalyzed aryl-alkenylation of alkenes

Scheme 7. Ni-catalyzed aryl-alkenylation of alkenes

Scheme 8. Ni-catalyzed aryl-fluoroalkenylation of alkenes

Scheme 9. Mechanistic studies

Scheme 10. Proposed mechanism

Scheme 11. Ni-catalyzed aryl-difluoroalkenylation of alkenes

Scheme 12. Synthetic transformations

Scheme 13. Ni-catalyzed aryl-allylation of alkenes

Scheme 14. Ni-catalyzed aryl-allenylation of alkenes

Scheme 15. Reductive cyclization with alkynyl bromides

Scheme 16. Mechanistic studies

Scheme 17. Proposed mechanism

Scheme 18. Reductive cyclization with unsymmetrical alkynes

Scheme 19. Ni-catalyzed aryl-alkylation of alkenes

Scheme 20. Ni-catalyzed aryl-alkylation of alkenes

Scheme 21. Ni-catalyzed aryl-alkylation of alkenes

Scheme 22. Ni-catalyzed aryl-benzylation of alkenes

Scheme 23. Ni-catalyzed aryl-alkylation of alkenes

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

Scheme 25. Ni-catalyzed aryl-cyanation of alkenes

Scheme 26. Ni-catalyzed carbo-carboxylation of alkenes

Scheme 27. Synthesis of (-)-debromoflustramine B

Scheme 28. Synthesis of (+)-coixspirolactam A

Scheme 29. Ni-catalyzed carbo-carboxylation of alkenes

Scheme 30. Ni-catalyzed aryl-acylation of alkenes

Scheme 31. Ni-catalyzed aryl-amination of alkenes

Scheme 32. Ni-catalyzed divinylation of alkenes

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

Scheme 34. Ni-catalyzed acyl-alkylation of alkenes

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

Scheme 36. Ni-catalyzed intermolecular reductive difunctionalization of alkenes

Scheme 37. Ni-catalyzed reductive diarylation of styrenes

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

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

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

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