Facile N-Modification of NH-Tetrazoles via Rh(II)-Catalyzed N-H Insertion Involving Structurally Diverse Diazo Reagents

Abstract

A convenient method for the N-modification of NH-tetrazoles by the Rh(II)-catalyzed insertion reaction of diazocarbonyl compounds into the N-H bond has been proposed. A wide range of structurally diverse diazo reagents (including heterocyclic ones) as well as tetrazoles with different substituents in the fifth position can be used to prepare 2,5-disubstituted tetrazole derivatives in good and high yields and with high regioselectivity. It is shown that the regioselectivity of the reaction can decrease in the presence of electron withdrawing groups in the tetrazole, as well as in the presence of proton acids.