Ring-opening selenation of cyclobutanols: synthesis of γ-selenylated alkyl ketones through C–C bond cleavage

Abstract

An efficient and practical manganese-mediated ring-opening selenation of cyclobutanols is disclosed. The transformation has broad functionality tolerance, producing a variety of γ-selenylated alkyl ketones in synthetically useful yields. Mechanistically, the radical-promoted regioselective cyclic C–C bond cleavage and sp³ C–Se bond formation are involved.