Bentkowska, Katarzyna

Grainger, Rachel

Larrosa, Igor

Lepper, Thomas J.

Panigrahi, Adyasha

Spencer, Andrew

The cross-dehydrogenative arylation of benzylic C–H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free crossdehydrogenative arylation of benzylic C–H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules

Transition Metal-free Cross-Dehydrogenative Arylation of Unactivated Benzylic C–H Bonds

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