Catalytic, Diastereoselective 1,2-Difluorination of Alkenes.

J Am Chem Soc

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.

Published: April 2016

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5097459PMC
http://dx.doi.org/10.1021/jacs.6b02391DOI Listing

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