Fluorocyclization of -Propargylamides to Oxazoles by Electrochemically Generated ArIF.

A sustainable synthesis of 5-fluoromethyl-2-oxazoles by use of electrochemistry has been demonstrated. Hypervalent ArIF is generated by direct electrochemical oxidation of iodoarene ArI in EtN·5HF and mediates the fluorocyclization of -propargylamides to 5-fluoromethyl-2-oxazoles. The stoichiometry in ArI turned out to be a key parameter in controlling the product selectivity. This electrochemical protocol provides access to fluorinated oxazoles starting from simply available -propargylamides with yields up to 65% and offers a green alternative over conventional reagent-based approaches.