Work

Thiol Catalyzed Aerobic Debenzylation of Alcohols and Amines

Year: 2021

Type: preprint

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.

Source: ChemRxiv

DOI: 10.26434/chemrxiv-2021-w3q1d

Authors: Samuel Lardy, Valerie Schmidt

Institution: University of California San Diego

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Award: Radical-Mediated Atom-Transfer Strategies for Chemical Synthesis

OpenAlex ID: W3191678862

Cites: 51

Cited by: 1

Related to: 10