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Homologation of aryl ketones to long-chain ketones and aldehydes via C-C bond cleavage.

ABSTRACT: Transition metal-catalyzed C-C bond cleavage is a powerful tool for the reconstruction of a molecular skeleton. We report herein the multi-carbon homologation of aryl ketones to long-chain ketones and aldehydes via ligand-promoted Ar-C(O) bond cleavage and subsequent cross coupling with alkenols. Various (hetero)aryl ketones are compatible in the reaction, affording the corresponding products wtih good to excellent yields with high regioselectivity. Further applications in the late-stage diversification of biologically important molecules demonstrate the synthetic utility of this protocol. Mechanistic studies indicate that the ligand plays an important role in both C-C bond cleavage and the asymmetric migration-insertion process.

SUBMITTER: Wang X

PROVIDER: S-EPMC9204744 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Homologation of aryl ketones to long-chain ketones and aldehydes via C-C bond cleavage.

Wang Xing X Li Ling-Jun LJ Wang Zhen-Yu ZY Xu Hui H Dai Hui-Xiong HX

iScience 20220602 7

Transition metal-catalyzed C-C bond cleavage is a powerful tool for the reconstruction of a molecular skeleton. We report herein the multi-carbon homologation of aryl ketones to long-chain ketones and aldehydes via ligand-promoted Ar-C(O) bond cleavage and subsequent cross coupling with alkenols. Various (hetero)aryl ketones are compatible in the reaction, affording the corresponding products wtih good to excellent yields with high regioselectivity. Further applications in the late-stage diversi ...[more]

PMID: 35720269

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