Selenolate Anion as an Organocatalyst: Reactions and Mechanistic Studies

Abstract

Abstract A new organocatalyst, the selenolate anion [RSe] – , generated from bench‐stable and commercially available diphenyl diselenide or from phenyl benzyl selenide (10 mol%) is introduced. Benchmarking is performed in the conversion of benzylic chlorides into trans ‐stilbenes selectively at room temperature. Mechanistic studies support the intermediacy of the selenolate anion and of 1,2‐diphenylethyl phenyl selenide. magnified image