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

Andrew Spencer, Rachel Grainger, Adyasha Panigrahi, Thomas J. Lepper, Katarzyna Bentkowska, Igor Larrosa

Research output: Contribution to journalArticlepeer-review

Abstract

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.
Original languageEnglish
JournalChemical Communications
Publication statusAccepted/In press - 19 Oct 2020

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