Hydrodehalogenation of α-Haloketones with Iodotrimethylsilane

Abstract

Two years ago I delineated a hydrodehalogenation procedure for α-haloketones¹ which was conceived on the HSAB basis (Saville rule). In that communication the possible use of iodo- and alkylthiotrimethylsilanes was explicitly adumbrated. After submitting a related report on deoxygenation of α-ketols² with iodotrimethylsilane which implied the intermediacy of α-iodoketones and their in situ reduction, I set about demonstrating, just to satisfy myself, the general effectiveness of iodotrimethylsilane for removal of halogen atoms in the α-positions of ketones. These results were withheld from publication at the time. However, a recent disclosure by Olah et al. ³ prompts deposition on record of this work.