Photocatalytic Defluorinative α-Aminoalkylation of Allylic Difluorides.

J Org Chem

Canadian Centre for Research in Advanced Fluorine Technologies, Department of Chemistry and Biochemistry, University of Lethbridge, 4401 University Drive, Lethbridge, Alberta T1K 3M4, Canada.

Published: September 2024

A photocatalytic process was devised to synthesize monofluoroalkenes via defluorinative functionalization of allylic difluorides. -Alkylanilines are used as precursors to α-aminoalkyl radicals, which undergo regioselective addition to allylic difluorides, and subsequent SET and fluoride elimination produce monofluoroalkenes. C-C bond formation on the aniline is site-selective for the least substituted carbon α to nitrogen.

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http://dx.doi.org/10.1021/acs.joc.4c01861DOI Listing

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