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

Org Lett. 2018 Feb 2;20(3):728-731. doi: 10.1021/acs.orglett.7b03862. Epub 2018 Jan 10.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't