Addition of 2-(Trimethylsilyl)thiazole to Alkyl and Aryl Perfluoroalkyl Ketones: Synthesis of Fluorinated Tertiary Alcohols and α-Hydroxy Aldehydes

Abstract

The spontaneous addition of 2-(trimethylsilyl)thiazole (2-TST, 1) to various alkyl and aryl perfluoroalkyl ketones 2 in THF at 80°C affords the corresponding tertiary alcohols 4 which by thiazolyl-to-formyl conversion are transformed into fluorinated α-hydroxy aldehydes 6. The formation of silyl enol ether side products is observed in the reaction of 2-TST 1 with alkyl ketones 2b-e.