A convenient synthesis of β-phenylselenocarbonyl compounds by In-TMSCl promoted cleavage of diphenyl diselenide and subsequent Michael addition

Abstract

A simple and convenient procedure has been developed for the synthesis of β-phenylselenocarbonyl compounds by a one-pot reaction of diphenyl diselenide and α,β-unsaturated ketones, aldehydes, esters and nitriles in the presence of indium metal-trimethylsilyl chloride under sonication. Presumably, the In-TMSCl reagent system reacts with diphenyl diselenide to form an intermediate, PhSeSiMe₃, which then undergoes Michael addition with the α,β-unsaturated carbonyl compounds to produce the products.