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Updated: Nov 3, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Radical cascade synthesis of azoles via tandem hydrogen atom transfer
Andrew D Chen1, James H Herbort1, Ethan A Wappes1
1Department of Chemistry and Biochemistry, The Ohio State University Columbus OH 43210 USA nagib.1@osu.edu.
Abstract:
A radical cascade strategy for the modular synthesis of five-membered heteroarenes (e.g. oxazoles, imidazoles) from feedstock reagents (e.g. alcohols, amines, nitriles) has been developed. This double C-H oxidation is enabled by in situ generated imidate and acyloxy radicals, which afford regio- and chemo-selective β C-H bis-functionalization. The broad synthetic utility of this tandem hydrogen atom transfer (HAT) approach to access azoles is included, along with experiments and computations that provide insight into the selectivity and mechanism of both HAT events.
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