Transition metal-free cross-dehydrogenative arylation of unactivated benzylic C–H bonds
2020
Spencer, Andrew R. A. | Grainger, Rachel | Panigrahi, Adyasha | Lepper, Thomas J. | Bentkowska, Katarzyna | Larrosa, Igor
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 cross-dehydrogenative 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.
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