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Catalytic, Diastereoselective 1,2-Difluorination of Alkenes.

ABSTRACT: We describe a direct, catalytic approach to the 1,2-difluorination of alkenes. The method utilizes a nucleophilic fluoride source and an oxidant in conjunction with an aryl iodide catalyst and is applicable to alkenes with all types of substitution patterns. In general, the vicinal difluoride products are produced with high diastereoselectivities. The observed sense of stereoinduction implicates anchimeric assistance pathways in reactions of alkenes bearing neighboring Lewis basic functionality.

SUBMITTER: Banik SM

PROVIDER: S-EPMC5097459 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Catalytic, Diastereoselective 1,2-Difluorination of Alkenes.

Banik Steven M SM Medley Jonathan William JW Jacobsen Eric N EN

Journal of the American Chemical Society 20160412 15

We describe a direct, catalytic approach to the 1,2-difluorination of alkenes. The method utilizes a nucleophilic fluoride source and an oxidant in conjunction with an aryl iodide catalyst and is applicable to alkenes with all types of substitution patterns. In general, the vicinal difluoride products are produced with high diastereoselectivities. The observed sense of stereoinduction implicates anchimeric assistance pathways in reactions of alkenes bearing neighboring Lewis basic functionality. ...[more]

PMID: 27046019

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