Progress in the Synthesis of C(sp2)—C(sp3) Bond by Reductive Heck Reactions of Alkenes

doi:10.6023/cjoc202105016

Abstract

Transition-metal catalyzed C(sp²)—C(sp³) cross-coupling is of great significance in organic chemistry for synthesizing complex natural products and pharmaceutical molecules. Recently, reductive Heck reactions have emerged as one of the simple and efficient strategies for the construction of C(sp²)—C(sp³) bond. The recent advances in the reductive Heck reactions of alkenes are summarized on the basis of different hydride sources. The related mechanisms are provided, and the future development of this field is also prospected.

Key words: alkene, transition-metal catalysis, reductive Heck reaction, C(sp²)—C(sp³) formation

Cite this article

Xiao Xiao, Jianchao Liu. Progress in the Synthesis of C(sp²)—C(sp³) Bond by Reductive Heck Reactions of Alkenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3349-3365.

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Fig. & Tab. 30

Scheme 1. Mechanism for the reductive Heck reaction

Scheme 2. Syntheses of (–)-lycoramine and (–)-galanthamine

Scheme 3. Syntheses of (+)-PI-220 and (+)-3-epi-furaquinocin C

Scheme 4. Indoline synthesis via the reductive Heck reaction

Scheme 5. Proposed mechanism for palladium-catalyzed dearomative reductive Heck reaction of indoles

Scheme 6. Proposed mechanism for palladium-catalyzed 1,2- hydrovinylation of 1,3-dienes

Scheme 7. Tetrahydropyridines synthesis via the reductive Heck cyclization

Scheme 8. Palladium-catalyzed intermolecular hydroarylation of alkenes

Scheme 9. Proposed mechanism for palladium-catalyzed intermolecular hydroarylation of alkenes

Scheme 10. Proposed mechanism for transiently directed reductive Heck reaction of alkenes

Scheme 11. Palladium-catalyzed intramolecular Heck reaction of allyl aryl ethers

Scheme 12. Palladium-catalyzed asymmetric reductive Heck desymmetrization of cyclopentenes

Scheme 13. Proposed mechanism for the Mizoroki-Heck/reductive Heck cascade reactions

Scheme 14. Palladium-catalyzed asymmetric reductive Heck reaction of thioesters

Scheme 15. Synthesis of chiral indanones based upon an asymmetric reductive Heck reaction

Scheme 16. Reductive Heck reaction versus the Mizoroki-Heck reaction

Scheme 17. Palladium-catalyzed asymmetric reductive Heck reaction of aryl halides

Scheme 18. Asymmetric reductive Heck reaction with monodentate phosphoramidite ligand

Scheme 19. Palladium catalyzed reductive Heck reaction of unactivated alkenes

Scheme 20. Proposed mechanism for the reductive Heck reaction of unactivated alkenes

Scheme 21. Palladium catalyzed anti-Michael reductive Heck reaction of α,β-unsaturated esters

Scheme 22. Palladium catalyzed reductive Heck reaction of α,β- unsaturated ketones with aryl iodides

Scheme 23. Palladium catalyzed reductive Heck reaction of inactivated olefins with aryl bromides

Scheme 24. Proposed mechanism for the reductive Heck reaction of inactivated olefins with aryl bromides

Scheme 25. Reductive Heck reaction of unactivated aliphatic alkenes with organohalides

Scheme 26. Nickel-catalyzed asymmetric reductive Heck reaction of inactivated olefins

Scheme 27. Anti-Markovnikov selective reductive Heck reaction

Scheme 28. Reductive Heck reaction using water as a hydride source

Scheme 29. Proposed mechanism for Pd-catalyzed asymmetric reductive Heck reaction

Scheme 30. Nickel-catalyzed asymmetric reductive Heck reaction

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烯烃参与的还原Heck反应构建C(sp²)—C(sp³)键研究进展

Progress in the Synthesis of C(sp²)—C(sp³) Bond by Reductive Heck Reactions of Alkenes

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烯烃参与的还原Heck反应构建C(sp2)—C(sp3)键研究进展