Regio- and stereoselective divergent cross-coupling of alkynes and disubstituted alkenes via photoredox cobalt dual catalysis

Literature Information

Publication Date 2023-10-28
DOI 10.1039/D3QO01281F
Impact Factor 5.281
Authors

Yan-Lin Li, Kun Cui, Zheng-Yang Gu, Hu He


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Abstract

Achieving divergent synthesis from the same substrates quickly to generate different products remains an attractive objective in synthetic chemistry and the medicinal industry. Here, we report a discovery of highly selective divergent cross-coupling of alkynes and disubstituted alkenes by merging visible light photoredox and cobalt catalysis. Under otherwise identical conditions, the use of either a hemilabile P,N-ligand or a strong bidentate diphosphine ligand leads to ene-type coupling or reductive coupling of alkynes and Tulipalin A, producing stereodefined 1,4-diene or trisubstituted alkene products, respectively. The approaches feature considerable advantages for the straightforward synthesis of stereodefined multiple substituted alkenes, such as easily available substrates, low catalyst loading of an organophotocatalyst, excellent regio- and stereoselectivity, good functional group tolerance, and mild reaction conditions. Reasonable catalytic reaction pathways from the same cobaltacyclopentene intermediate have been proposed.

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Inside front cover

2023-12-05 Cover

DOI: 10.1039/D3CC90393A

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Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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