Nickel-Catalyzed Reductive Decarboxylative Coupling of Diacyl Peroxides with Aryl/Vinyl Halides

In this work, we utilized alkyl diacyl peroxides as the decarboxylative substrates, which are derived from the condensation of readily available alkyl acids with mCPBA, to couple with a variety of aryl and vinyl halides under a Ni-catalyzed cross-electrophile coupling platform, effectively affording...

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Bibliographic Details
Published in:ACS catalysis 2024-08, Vol.14 (16), p.12192-12198
Main Authors: Qiu, Canbin, Chen, Qifa, Gong, Hegui
Format: Article
Language:English
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Summary:In this work, we utilized alkyl diacyl peroxides as the decarboxylative substrates, which are derived from the condensation of readily available alkyl acids with mCPBA, to couple with a variety of aryl and vinyl halides under a Ni-catalyzed cross-electrophile coupling platform, effectively affording C­(sp3)–C­(sp2) bonds. The method stresses the high compatibility of alkyl diacyl peroxides as strong oxidants with the Ni/Zn-mediated reductive conditions. With assistance of LiI and catalytic CuI, the kinetic labile alkyl diacyl peroxide underwent facile in situ Barton-decarboxylative iodination to afford alkyl iodide as the actual coupling partners. The present method showcases a broad substrate scope for both alkyl acids and aryl/vinyl electrophiles. It offers the advantage of iodo-selectivity for the alkylation of aryl iodides, even those bearing highly competing bromine groups, including the challenging vicinal bromoiodobenzene. Consequently, it enables the development of a one-pot selective dialkylation process.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.4c04002