Jump to main content
Jump to site search


Radical cascade synthesis of azoles via tandem hydrogen atom transfer

Author affiliations

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

Back to tab navigation

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, Advance Article
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, Advance Article , DOI: 10.1039/C9SC06239D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements