Construction of β-Amino Sulfones from Sodium Metabisulfite via a Radical 1,4-Amino Migration.

Abstract

A three-component reaction of alkenyl-tethered oxime ethers, sodium metabisulfite, and aryldiazonium tetrafluoroborates under mild conditions is developed. This reaction proceeds at room temperature without any oxidants or additives, affording β-amino sulfones with good functional group tolerance through aminosulfonylation of unactivated alkene. Mechanistic studies show that this transformation undergoes a radical process, including radical trapping with sulfur dioxide and radical 1,4-amino migration.