Synthesis of Acrylonitriles through an FeCl3-Catalyzed Domino Propargylic Substitution/Aza-Meyer-Schuster Rearrangement Sequence

Abstract

Nontoxic cyanide source: An unprecedented route to acrylonitriles by employing propargylic alcohols and para-tolylsulfonohydrazide as a combined cyano source has been developed (see scheme). This efficient and practical cyanation reaction proceeds through an FeCl3-catalyzed domino propargylic substitution/aza-Meyer–Schuster rearrangement sequence, the rearrangement process of which is reported for the first time.