Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinated <i>N</i>H-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%.

SUBMITTER: Alexander JR 

PROVIDER: S-EPMC8201930 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature