Radical borylation of vinyl azides with NHC-boranes: divergent synthesis of α-boryl ketones and borylated triazoles

Abstract

A divergent radical borylation of vinyl azides with N-heterocyclic carbene (NHC) boranes in the presence of ^tBuSH is described. The protocol enables the divergent synthesis of α-boryl ketones and borylated triazoles with excellent functional group tolerance and a broad substrate scope. Remarkably, this work shows that vinyl azides can serve as unprecedented five-atom synthons for the construction of 1,2,3-triazoles without N₂ extrusion.