Selenolate Anion as an Organocatalyst: Reactions and Mechanistic Studies

A new organocatalyst, the selenolate anion [RSe](-), generated from bench-stable and commercially available diphenyl diselenide or from phenyl benzyl selenide (10mol%) 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.