Transition metal-free cross-dehydrogenative arylation of unactivated benzylic C-H bonds

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 no...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) Vol. 56; no. 92; pp. 14479 - 14482
Main Authors: Spencer, Andrew R. A., Grainger, Rachel, Panigrahi, Adyasha, Lepper, Thomas J., Bentkowska, Katarzyna, Larrosa, Igor
Format: Journal Article
Language:English
Published: CAMBRIDGE Royal Soc Chemistry 19.11.2020
Subjects:
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
F BONDS
FUNCTIONALIZATION
C(SP)-H BONDS
ACTIVATION
COUPLING REACTIONS
LIGHT
OXIDATIVE ARYLATION
IRON
FLUORINATION
FLUORIDES
ISSN:1359-7345, 1364-548X, 1364-548X
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Summary: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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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d0cc06212j