Recent Advances in Visible-Light-Mediated Copper-Catalyzed Difunctionalization of 1,3-Enynes

doi:10.6023/cjoc202604003

Abstract

Visible-light-mediated copper-catalyzed 1,3-enyne difunctionalization represents an efficient strategy for the cons- truction of polysubstituted allenes and propargylic compounds. Systematic advances in visible-light-mediated copper-catalyzed difunctionalization of 1,3-enynes in recent years are reviewed. Their applications in the difunctionalization of 1,3-enynes are elaborated by category according to different types of radical precursors. Reaction mechanisms, selectivity regulation mechanisms, influencing factors as well as advances in asymmetric catalytic reactions are discussed. Finally, the existing challenges in this field are outlined, and prospects for future research are proposed.

Key words: photoredox catalysis, copper catalysis, 1,3-enyne, allene, difunctionalization

Cite this article

Peiwen Liu, Fu Ye, Weiming Yuan. Recent Advances in Visible-Light-Mediated Copper-Catalyzed Difunctionalization of 1,3-Enynes[J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2563-2580.

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Fig. & Tab. 18

Scheme 1. Visible-light-mediated copper-catalyzed difunctionalization of 1,3-enynes

Scheme 2. Decarboxylative 1,4-carbocyanation of 1,3-enynes via photoredox/copper dual catalysis

Scheme 3. Enantioselective decarboxylative 1,4-carbocyanation of 1,3-enynes via photoredox/copper dual catalysis

Scheme 4. Enantioselective 1,2-carbocyanation of 1,3-enynes via photoredox/copper dual catalysis

Scheme 5. 1,4-Alkylcyanation of 1,3-enynes enabled by photoredox/copper dual catalysis

Scheme 6. Difunctionalization of 1,3-enynes via 1,5-HAT by photoredox/copper dual catalysis

Scheme 7. Three-component radical annulation of 1,3-enynes, cyclobutanone oxime esters and arylboronic acids enabled by photoinduced copper catalysis

Scheme 8. 1,4-Cyanoalkylarylation of 1,3-enynes enabled by photoredox/copper dual catalysis

Scheme 9. Enantioselective decarboxylative 1,2-cyanoalkyl esterification of 1,3-enynes enabled by photoinduced copper catalysis

Scheme 10. Enantioselective 1,2-cyanoalkyl esterification of 1,3-enynes enabled by photoinduced copper catalysis

Scheme 11. Acyl-trifluoromethylthiolation of 1,3-enynes enabled by photoredox/copper dual catalysis

Scheme 12. Photoredox/copper-catalyzed alkylcyanation of 1,3-enynes using sulfoxonium ylides as carbon radical precursors

Scheme 13. Photoredox/copper-catalyzed 1,4-arylcyanation of 1,3-enynes using thianthrenium salts as aryl radical precursors

Scheme 14. 1,4-Arylcyanation of 1,3-enynes enabled by photoredox/copper dual catalysis

Scheme 15. 1,4-Trifluoromethylaminocyanation of 1,3-enynes enabled by photoredox/copper dual catalysis

Scheme 16. 1,4-Amidocyanation of 1,3-enynes enabled by photoredox/copper dual catalysis

Scheme 17. 1,4-Perfluoroalkylcyanation of 1,3-enynes enabled by photoredox/copper dual catalysis

Scheme 18. 1,4-Difluoroalkylcyanation of 1,3-enynes enabled by photoredox/copper dual catalysis

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可见光介导铜催化1,3-烯炔的双官能团化反应进展