A Ritter-Type Route to N-Benzylamides by Multicomponent Reaction Based on p-(Trifluoromethyl)- p-quinols

Org Lett. 2018 Oct 19;20(20):6449-6452. doi: 10.1021/acs.orglett.8b02762. Epub 2018 Oct 5.

Abstract

A novel multicomponent reaction of p-(trifluoromethyl)- p-quinolsilyl ethers, ketones, and nitriles was developed for the efficient synthesis of p-trifluoromethylated N-benzylamides. The key step of the reaction involves the formation of an unstable condensation precursor in situ generated form the condensation of p-(trifluoromethyl)- p-quinolsilyl ethers with ketones. This work provides a significant expansion to the Ritter-type reaction, and the reaction can proceed under mild reaction conditions and tolerate various nitriles including both aryl and aliphatic nitriles.

Publication types

  • Research Support, Non-U.S. Gov't