Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

Abstract

A sustainable catalyst- and solvent-free Passerini-tetrazole three component reaction (PT-3CR) has been developed for the selective synthesis of benzoxaborol-tetrazoles for the first time. The synthetic potential of oxaboroles was demonstrated towards various functionalized tetrazoles, which are otherwise difficult to achieve through conventional PT-3CR from aromatic aldehydes/ketones. The reaction features high practicality, broad substrate scope and excellent yields (80–98%). Preliminary results of the asymmetric PT-3CR are also shown for the synthesis of chiral benzoxaboroles.