A formal vinylic substitution reaction for the synthesis of α,β-unsaturated enol esters and their anticancer potential

Abstract

Arylsulfonyl group-bearing α,β-unsaturated enol esters were readily assembled via the Cs₂CO₃-mediated union of 2-bromoallyl sulfones and cinnamic acids. The overall transformation is equivalent to an sp² carbon-oxygen coupling reaction, and therefore constitutes a formal vinylic substitution. Several of the products display promising levels of antiproliferative activities higher than that of the anticancer drug carboplatin. Thiophenol reacted with 2-bromoallyl sulfones under identical conditions to afford α-thiophenyl-α'-tosyl acetone via an apparent aerial oxidation.