Organic Chemistry

Thiol Catalyzed Aerobic Debenzylation of Alcohols and Amines

Authors

Abstract

We report a radical method for the removal of benzyl and p-methoxybenzyl groups from amines and alcohols using a selec-tive hydrogen-atom abstraction under aerobic conditions. The key usage of the strongly electrophilic thiyl radical derived from commercially available pentafluorothiophenol allowed for a chemoselective abstraction process leading to C-N or C-O bond cleavage. This approach is applicable to an array of alcohols and amines without addition of a stoichiometric external oxidant or hazardous reagents.

Content

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Supplementary material

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Supplemental Information
Additional optimization and mechanistic experiments, de-tailed experimental procedures, and full spectroscopic data for new compounds are provided.