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Herein, we report a direct α-C–H alkylation of alcohols with alkenes enabled by organic photoredox catalysis, in which the additive trimethylsilyl azide (TMSN3) plays a crucial role in the selective activation of the α-C–H bond of free alcohols. Both α-CF3-alkenes and acrylamides showed high efficiency and excellent chemoselectivity in this transformation, affording various γ-trifluoromethyl alcohols and γ-hydroxyl amides under mild conditions. The late-stage modification of several drug derivatives was achieved, and the synthetic utility of this protocol was further highlighted by the scaled-up reaction and several derivations of the products.
Duan et al. (Fri,) studied this question.