Deaminative metal-free reaction of alkenylboronic acids, sodium metabisulfite and Katritzky salts

Abstract

A convenient and efficient approach to (E)-alkylsulfonyl olefins via a metal/light-free three-component reaction of alkenylboronic acids, sodium metabisulfite and Katritzky salts is described. This alkylsulfonylation proceeds smoothly with a broad substrate scope, leading to diverse (E)-alkylsulfonyl olefins in moderate to good yields. During the process, excellent functional group tolerance is observed and sodium metabisulfite is used as the source of sulfur dioxide. Mechanistic studies show that the alkyl radical generated in situ from Katritzky salt via a single electron transfer with alkenylboronic acid or DIPEA is the key step for providing an alkyl radical intermediate, which undergoes further alkylsulfonylation with sulfur dioxide.