Synthesis of β-cyanoalkylsulfonylated vinyl selenides through a four-component reaction

Abstract

A mild copper-catalyzed four-component selenosulfonylation of alkynes, cycloketone oxime esters, DABCO (SO₂)₂ and diselenides has been developed. This method enables the rapid assembly of β-cyanoalkylsulfonylated vinyl selenides in moderate to good yields. Advantages of this protocol include a broad substrate scope, good functional group tolerance and the late-stage functionalization of complex molecules. Moreover, the potential utility of this methodology is demonstrated through simple oxidation of the products to access synthetically important alkynyl sulfones. Mechanistic studies suggest that a cyanoalkylsulfonyl radical intermediate is involved in this process.