Nucleophilic substitution reactions of and#945; hydroxyketones synthesis and structural studies of and#945; functionalized ketones

Abstract

An efficient protocol for the replacement of the hydroxyl group in 2-hydroxy1,2,2-triarylethanones has been developed using a variety of nucleophiles in the presence of Brønsted acid or Lewis acid. Nucleophilic substitution reactions such as arylation, fluorination, azidation and deoxygenation of and#945;-hydroxyketones occur to give and#945;-functionalized ketones. 2-Hydroxy-1,2,2-triarylethanones have been successfully converted into 1,2,2,2-tetraarylethanones (arylation), 2-fluoro-1,2,2- triarylethanones (fluorination), 2-azido-1,2,2-triarylethanones (azidation) and 1,2,2- triarylethanones (deoxygenation). newline