Catalytic Direct Regioselective Synthesis of Phosphonylated Tetrazoles from Aryl Diazonium Salts and Seyferth-Gilbert Reagent

Abstract

Here we report a Ag-catalyzed [3 + 2] cycloaddition reaction between aryl diazonium salts and Seyferth-Gilbert reagent in a regioselective manner. This operationally simple transformation proceeds in an atom-economical way under mild reaction conditions, providing facile access to a broad set of phosphonylated tetrazoles. The synthetic utility of this method is further showcased by a straightforward procedure from upstream aromatic amines, denitrogenation transformations, and preparation of a phosphonylated drug scaffold.