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Fluorocyclization of N-Propargylamides to Oxazoles by Electrochemically Generated ArIF2
John D Herszman1, Michael Berger1, Siegfried R Waldvogel1
1Institute of Organic Chemistry , Johannes Gutenberg University Mainz , Duesbergweg 10-14 , 55128 Mainz , Germany.
Abstract:
A sustainable synthesis of 5-fluoromethyl-2-oxazoles by use of electrochemistry has been demonstrated. Hypervalent ArIF2 is generated by direct electrochemical oxidation of iodoarene ArI in Et3N·5HF and mediates the fluorocyclization of N-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 N-propargylamides with yields up to 65% and offers a green alternative over conventional reagent-based approaches.
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