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  • Title: Photoredox Enabled Defluorinative Benzylation of Trifluoromethyl Alkenes with Alkylarenes.
    Author: Shi Y, Nie J, Wu Z, Ji X, Huang H.
    Journal: Org Lett; 2024 Jan 12; 26(1):100-105. PubMed ID: 38147046.
    Abstract:
    Herein, we report a photoredox enabled defluorinative benzylation of trifluoromethyl alkenes with readily available alkylarenes, which provides convenient access to a series of structurally valuable benzylated gem-difluoroalkenes under mild reaction conditions. The synthetic value of this protocol has been demonstrated by the transformations of several substrates bearing drug moieties, gram-scale reactions, and various further derivatizations of the gem-difluoroalkene products. The preliminary mechanistic investigations suggest a reaction pathway with rate-determining benzyl C-H bond cleavage of toluene followed by benzylic radical formation.
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