Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinated NH-1,2,3-triazoles

Abstract

The treatment of propargylic azides with silver(I) fluoride in acetonitrile was found to yield α-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction was regioselective and the products result from an initial [3,3] rearrangement. The reaction is demonstrated on >15 examples with yields ranging from 37% to 86%.