Visible-Light Copper Catalysis for the Synthesis of α‑Alkyl-Acetophenones by the Radical-Type Ring Opening of Sulfonium Salts and Oxidative Alkylation of Alkenes

Direct difunctionalization of simple alkenes has been treated as a powerful synthetic strategy for the construction of highly functionalized skeletons. In this study, direct oxidative coupling of sulfonium salts with alkenes was achieved under mild conditions by a blue-light-driven photoredox proces...

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Bibliographic Details
Published in:Organic letters 2023-05, Vol.25 (18), p.3260-3265
Main Authors: Li, Xuan, Li, Xufeng, Cui, Wenwen, Wu, Qilong, Wang, Linyuan, Lv, Jian, Yang, Daoshan
Format: Article
Language:English
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Summary:Direct difunctionalization of simple alkenes has been treated as a powerful synthetic strategy for the construction of highly functionalized skeletons. In this study, direct oxidative coupling of sulfonium salts with alkenes was achieved under mild conditions by a blue-light-driven photoredox process using a copper complex as a photosensitizer. This protocol allows regioselective synthesis of aryl/alkyl ketones from simple sulfonium salts and aromatic alkenes via selective C–S bond cleavage of sulfonium salts and oxidative alkylation of aromatic alkenes using dimethyl sulfoxide (DMSO) as a mild oxidant.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00990