Photoredox-Catalyzed 1,4-Peroxidation-Sulfonylation of Enynones: A Three-Component Radical Coupling Approach for the Synthesis of Highly Functionalized Allenes

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초록

An Eosin Y-catalyzed visible light-promoted 1,4-peroxidation–sulfonylation of enynones was achieved to give tetrasubstituted allenes. The photoredox catalysis of Eosin Y allowed the concomitant formation of peroxy and sulfonyl radicals, where the preferential peroxy radical addition to the alkene moiety of enynones resulted in the subsequent α-keto radical–sulfonyl radical cross couplings. The developed photoredox catalysis of Eosin Y demonstrates a regioselective 1,4-diradical addition strategy, opening up a new possibility of diradical functionalization of conjugate systems.

키워드

SULFINIC ACIDS; ALKENES; PEROXIDATION; EPOXIDATION
제목
Photoredox-Catalyzed 1,4-Peroxidation-Sulfonylation of Enynones: A Three-Component Radical Coupling Approach for the Synthesis of Highly Functionalized Allenes
저자
Bhatt, Divya; Miyake, Kosei; Nakamura, Shuichi; Kim, Hun Young; Oh, Kyungsoo
DOI
10.1021/acs.orglett.4c00517
발행일
2024-04
유형
Article
저널명
Organic Letters
권
26
호
15
페이지
2955 ~ 2959