Silicon mediated synthesis and selected transformations of β-chloroketones

A combination of tetrachlorosilane (TCS) and phenol in dichloromethane was found to be an efficient reagent for hydrochlorination of α,β-unsaturated ketones to afford the corresponding β-chloroketones in good yield at ambient temperature. Reactions of the titled compounds with TCS-NaN3 as well as with nitriles utilizing TCS-ZnCl2 to give 1,5-disubstituted tetrazole derivatives or β-amido ketones respectively are also described.