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Issue 9, 2020

Radical cascade synthesis of azoles via tandem hydrogen atom transfer

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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.

Graphical abstract: Radical cascade synthesis of azoles via tandem hydrogen atom transfer

Supplementary files

Article information


Submitted
10 Dec 2019
Accepted
24 Jan 2020
First published
31 Jan 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 2479-2486
Article type
Edge Article

Radical cascade synthesis of azoles via tandem hydrogen atom transfer

A. D. Chen, J. H. Herbort, E. A. Wappes, K. M. Nakafuku, D. N. Mustafa and D. A. Nagib, Chem. Sci., 2020, 11, 2479 DOI: 10.1039/C9SC06239D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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