可见光/镍协同催化烯烃和炔烃双官能团化反应研究进展

doi:10.6023/cjoc202109002

摘要/Abstract

可见光氧化还原催化与金属镍催化的联姻, 使得在极为温和条件下构建挑战性化学键成为可能. 然而, 大多数协同催化体系只能构建单一的碳-碳键或碳-杂原子键. 近些年来, 可见光/镍协同催化在烯烃及炔烃分子间双官能团化反应领域引起了广泛关注. 该协同催化级联模式可以一步构建多个化学键, 为复杂结构单元的快速高效构筑提供了温和且高选择性的方法. 对可见光/镍协同催化烯烃和炔烃分子间双官能团化反应的最新研究进展进行了概述.

关键词: 可见光催化, 镍催化, 协同催化, 烯烃, 炔烃, 双官能团化

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

引用此文

徐磊, 王方, 陈凡, 朱圣卿, 储玲玲. 可见光/镍协同催化烯烃和炔烃双官能团化反应研究进展[J]. 有机化学, 2022, 42(1): 1-15.

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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图/表 27

图式1. 可见光/镍协同催化烯烃和炔烃双官能团化反应

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

图式2. 光镍催化烯烃与芳胺环合反应

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

图式3. 光镍催化乙烯分子发散性双官能化反应

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

图式4. 光镍催化未活化烯烃级联酰胺芳基化反应

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

图式5. 光镍催化未活化烯烃非对映选择性氮酰化反应

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

图式6. 光镍催化烷氧基羰基环化交叉偶联级联反应

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

图式7. 光镍催化烯烃三组分烷基芳基化反应

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

图式8. 光镍催化烯烃三组分双碳官能化反应

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

图式9. 光镍催化烯烃硼酸酯烷基芳基化反应

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

图式10. 光镍催化乙烯基硼酸酯脱羧烷基芳基化反应

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

图式11. 光镍催化乙烯基硼酸酯还原双碳官能化反应

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

图式12. 光镍催化乙烯硼酸酯双碳偶联-脱硼串联反应

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

图式13. 光镍催化烯烃1,2-芳基-氨基烷基化反应

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

图式14. 光镍催化烯烃烷基芳基化反应

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

图式15. 光镍催化烯烃烷基芳基化反应

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

图式16. 光镍催化烯烃砜基芳基化反应

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

图式17. 光镍协同催化二烯级联交叉偶联反应

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

图式18. 光镍协同催化烯烃碳硅化反应

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

图式19. 光镍催化烯烃胺化芳基化反应

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

图式20. 光镍催化烯烃不对称烷基芳基化反应

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

图式21. 光镍催化烯烃不对称酰基氨基甲酰化反应

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

图式22. 光镍催化炔烃顺式烷基芳基化反应

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

图式23. 镍催化草酸铯盐的串联反应

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

图式24. 光镍催化炔烃立体发散性砜基芳基化反应

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

图式25. 光镍催化炔烃1,2-烷基芳基化反应

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

图式26. 光镍催化炔烃环化烷基化反应

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

图式27. 光镍催化炔烃1,2-溴化芳基化反应

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

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