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Dehydration of amides to nitriles under conditions of a catalytic appel reaction

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journal contribution
posted on 26.01.2018, 12:34 by Sergei A. Shipilovskikh, Vladimir Yu Vaganov, Elena I. Denisova, Aleksandr E. Rubtsov, Andrei Malkov
A highly expedient protocol for a catalytic Appel-type dehydration of amides to nitriles has been developed that employs oxalyl chloride and triethylamine along with triphenylphosphine oxide as a catalyst. The reactions are usually complete in less than 10 min with only a 1 mol % catalyst loading. The reaction scope includes aromatic, heteroaromatic, and aliphatic amides, including derivatives of α-hydroxy and α-amino acids.

Funding

The authors thank Russian Science Foundation for grant 15-13-00092.

History

School

  • Science

Department

  • Chemistry

Published in

Org Lett

Citation

SHIPILOVSKIKH, S.A. ...et al., 2018. Dehydration of amides to nitriles under conditions of a catalytic appel reaction. United States, Organic Letters, 20 (3), pp.728–731.

Publisher

© American Chemical Society (ACS)

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2018-01-10

Notes

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/10.1021/acs.orglett.7b03862.

eISSN

1523-7052

Language

en

Location

United States

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