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. 2024 Sep 20;89(18):13669-13677.
doi: 10.1021/acs.joc.4c01861. Epub 2024 Sep 4.

Photocatalytic Defluorinative α-Aminoalkylation of Allylic Difluorides

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Photocatalytic Defluorinative α-Aminoalkylation of Allylic Difluorides

Taylor Semeniuk et al. J Org Chem. .

Abstract

A photocatalytic process was devised to synthesize monofluoroalkenes via defluorinative functionalization of allylic difluorides. N-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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