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Dehydration of Amides to Nitriles under Conditions of a Catalytic Appel Reaction

Sergei A. Shipilovskikh , Vladimir Y. Vaganov, Elena I. Denisova, Aleksandr E. Rubtsov* and Andrei V. Malkov*

*Perm State University, Bukireva 15, Perm 614990, Russia; Loughborough University, Loughborough, Leicestershire LE11 3TU, U.K., Email: Rubtsovpsu.ru, A.Malkovlboro.ac.uk

S. A. Shipilovskikh, V. Yu. Vaganov, E. I. Denisova, A. E. Rubtsov, A. V. Malkov, Org. Lett., 2018, 20, 728-731.

DOI: 10.1021/acs.orglett.7b03862 (free Supporting Information)


Abstract

A highly expedient catalytic Appel-type dehydration of amides to nitriles in the presence of oxalyl chloride and triethylamine along with triphenylphosphine oxide as a catalyst is usually complete in less than 10 min. The reaction tolerates aromatic, heteroaromatic, and aliphatic amides, including derivatives of α-hydroxy and α-amino acids.


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proposed mechanism



Key Words

Nitriles, Appel Reaction


ID: J54-Y2018