Recent Advances in Photoredox/Nickel Dual-Catalyzed Difunctionalization of Alkenes and Alkynes

doi:10.6023/cjoc202109002

Abstract

The merger of visible-light photoredox catalysis and nickel catalysis makes it possible to forge challenging chemical bonds under mild conditions. Nevertheless, most of these transformations only construct a single carbon-carbon bond or carbon-heteroatom bond in one operation. In recent years, photoredox/nickel dual catalysis has attracted widespread attention in the field of catalytic difunctionalization of alkenes and alkynes. The synergistic cascade mode enables the construction of multiple chemical bonds in one single pot, providing a mild, efficient and selective protocol for the rapid assembly of complex structural motifs. The latest progress in the photoredox/nickel dual-catalyzed difunctionalization reactions of olefins and alkynes is summarized.

Key words: photoredox catalysis, nickel catalysis, synergistic catalysis, alkene, alkyne, difunctionalization

Cite this article

Lei Xu, Fang Wang, Fan Chen, Shengqing Zhu, Lingling Chu. Recent Advances in Photoredox/Nickel Dual-Catalyzed Difunctionalization of Alkenes and Alkynes[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 1-15.

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Fig. & Tab. 27

Scheme 1. Photoredox/nickel dual-catalyzed difunctionalizations of alkenes and alkynes

Scheme 2. Cyclization reaction of aromatic amines with alkenes by dual photoredox/nickel catalysis

Scheme 3. Divergent difunctionalization of ethylene via dual nickel/photoredox catalysis

Scheme 4. Cascade amidoarylation of unactivated olefins via dual nickel/photoredox catalysis

Scheme 5. Diastereoselective amidoacylation of unactivated olefins via dual nickel/photoredox catalysis

Scheme 6. Alkoxycarbonyl radical cyclization cross-coupling cascade reaction via dual nickel/photoredox catalysis

Scheme 7. Three-component alkylarylation of alkenes via dual nickel/photoredox catalysis

Scheme 8. Three-component carbofunctionalization of alkenes via dual nickel/photoredox catalysis

Scheme 9. Alkylarylation of vinyl boronic esters via dual nickel/photoredox catalysis

Scheme 10. Decarboxylative alkylarylation of vinyl boronic esters via dual nickel/photoredox catalysis

Scheme 11. Reductive dicarbofunctionalization of vinyl boronates via dual nickel/photoredox reductive catalysis

Scheme 12. Sequential alkylarylation and deborylation of vinyl boronates via dual nickel/photoredox catalysis

Scheme 13. 1,2-Aryl-aminoalkylation of alkenes via dual nickel/photoredox catalysis

Scheme 14. Alkylalkylation reaction of alkenes via dual nickel/photoredox catalysis

Scheme 15. Alkylalkylation reaction of alkenes via dual nickel/photoredox catalysis

Scheme 16. Sulfonylalkylation alkylation reaction of alkenes via dual nickel/photoredox catalysis

Scheme 17. Photoredox and nickel dual catalyzed cascade cross-coupling of dienes

Scheme 18. Carbosiylation of alkenes via dual nickel/ photoredox catalysis

Scheme 19. Aminoarylation of alkenes via dual nickel/ photoredox catalysis

Scheme 20. Asymmetric alkylalkylation of alkenes via dual nickel/photoredox catalysis

Scheme 21. Asymmetric acyl-carbamoylation of alkenes via dual nickel/photoredox catalysis

Scheme 22. syn-Alkylarylation of alkynes via dual nickel/photoredox catalysis

Scheme 23. Radical cascade reaction of cyclic oxalates via photoredox/nickel catalysis

Scheme 24. Stereodivergent sulfonylarylation of alkynes via dual nickel/photoredox catalysis

Scheme 25. 1,2-Alkylarylation of alkynes via dual nickel/photoredox catalysis

Scheme 26. Alkylative cyclization of alkynes via dual nickel/photoredox catalysis

Scheme 27. 1,2-Bromoarylation of alkynes via photoredox/ nickel catalysis

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