Ni(ii)-catalyzed nucleophilic substitution for the synthesis of allenylselenide

Abstract

A method for synthesizing allenylselenides has been developed using readily available propargyl carbonate and phenylselenol. The reaction is catalyzed by Ni(II) and proceeds via a migratory insertion and β-oxygen elimination mechanism. Due to the strong interaction between Se and Ni leading to catalyst deactivation, zinc salt was used to mitigate the deleterious effects of Se anions on the catalyst, thereby facilitating the successful synthesis of the target products.