α,α-Difluoro-α-phenylsulfanyl-α- trimethylsilylmethane as a difluoromethyl building block: A general strategy to α,α-difluoromethyl aryl ketones

Abstract

The synthetic utility of α,α-difluoro-α-phenylsulfanyl- α-trimethylsilylmethane (PhSCF 2 SiMe 3 ; 1) as a difluoromethyl building block providing a general strategy to α,α-difluoromethyl aryl ketones was demonstrated. Oxidation, by using m-chloroperoxybenzoic acid, of the readily available 1-aryl-2,2-difluoro- 2-phenylsulfanyl-1-trimethylsiloxyethanes obtained from fluoride-catalyzed nucleophilic addition of PhSCF 2 SiMe 3 with aromatic aldehydes followed by flash vacuum pyrolytic elimination provided α,α-difluoromethyl aryl ketones in moderate overall yields. © 2011 Published by Elsevier B.V. All rights reserved.