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Herein, we present a chemoselective strategy for the divergent synthesis of γ-trifluoromethyl alcohols and difluorohomoallyl alcohols via photoredox-catalyzed hydroxyalkylation of α-CF alkenes with primary/secondary alcohols. Both products can further undergo base-mediated intramolecular defluorinative cyclization to construct monofluorinated dihydrofurans in a one-pot process. Through controllable C-F bond cleavage, this approach enables streamlined synthesis of three types of fluorinated products from abundant and inexpensive raw materials under mild photoredox conditions.
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http://dx.doi.org/10.1021/acs.orglett.5c02242 | DOI Listing |