A New Method for Synthesis of Trifluoromethyl-Substituted Phenols and Anilines

Abstract

Triethyl(trifluoromethyl)silane and tri-n-butyl(trifluoromethyl)silane silane were found to react with quinones by addition to one of the carbonyl carbon atoms, giving dienones containing geminal trifluoromethyl and trialkylsiloxy substituents. These reactions were catalyzed by a variety of basic compounds. Quinones found to undergo this process include 1,2- and 1,4-benzoquinones (some bearing alkyl substituents), naphthoquinone, anthraquinone and phenanthrenequinone. Most of the resulting dienones gave (trifluoromethyl)phenols on dissolving metal reduction, and one was subjected to reductive amination to give (trifluoromethyl)aniline. © 1989, American Chemical Society. All rights reserved.