Cooperative Photoredox and N‑Heterocyclic Carbene Catalysis Suzuki–Miyaura-Type Reaction: Radical Coupling of Aroyl Fluorides and Alkyl Boronic Acids

An intermolecular Suzuki–Miyaura-type reaction of benzoyl fluorides with alkyl boronic acids to synthetic ketone was revealed by cooperative N-heterocyclic carbene (NHC) and photoredox catalysis. Various alkyl boric acids can be converted into alkyl radicals without external oxidants or activators....

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Bibliographic Details
Published in:Organic letters 2024-03, Vol.26 (8), p.1728-1733
Main Authors: Li, Shihao, Zhang, Chaoyang, Wang, Sheng, Yang, Wenqing, Fang, Xinru, Fan, Shilu, Zhang, Qi, Li, Xiao-Xuan, Feng, Yi-Si
Format: Article
Language:English
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Summary:An intermolecular Suzuki–Miyaura-type reaction of benzoyl fluorides with alkyl boronic acids to synthetic ketone was revealed by cooperative N-heterocyclic carbene (NHC) and photoredox catalysis. Various alkyl boric acids can be converted into alkyl radicals without external oxidants or activators. Moreover, the catalytic system was feasible for the difunctionalization of styrenes via a radical relay process. Mechanistic experiments suggested that the benzoate anion intermediate might play a unique role in this reaction system.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00334