Metal Triflate Catalyzed Reactions of Alkenes, NBS, Nitriles, and TMSN₃:  Synthesis of 1,5-Disubstituted Tetrazoles

Abstract

A versatile and highly efficient protocol for the synthesis of 1,5-disubstituted tetrazoles has been developed by metal triflate catalyzed one-pot reaction of alkenes, NBS, nitriles, and TMSN3. Among the metal triflates, Zn(OTf)2 was found to be the best catalyst. Use of different combinations of alkenes and nitriles generate a variety of 1,5-disubstituted tetrazoles containing an additional alpha-bromo functionality of the N1-alkyl substituent.