N-Iodosuccinimide-Promoted [3+2] Annulation Reaction of Aryldiazonium Salts with Guanidines To Construct Aminotetrazoles

A N-iodosuccinimide (NIS)-promoted [3 + 2] annulation reaction of aryldiazonium salts with guanidines has been developed for the construction of previously elusive 2-aryl-5-amino-2H-tetrazoles. This transformation takes advantage of readily available starting materials, proceeds under metal-free, mild, and robust conditions, and holds broad functional group compatibility. The utility of this protocol is further manifested via coupling, annulation, deamination, and denitrogenation derivatizations.

Automated summary

A novel N-iodosuccinimide-promoted [3 + 2] annulation reaction has been developed for the synthesis of 2-aryl-5-amino-2H-tetrazoles, which were previously difficult to access. The reaction utilizes readily available starting materials, operates under metal-free conditions, and exhibits broad functional group compatibility. The utility of this protocol is demonstrated through various derivatization reactions such as coupling, annulation, deamination, and denitrogenation.