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RESEARCH PRODUCT

Fluorocyclization of N-Propargylamides to Oxazoles by Electrochemically Generated ArIF2

Siegfried R. WaldvogelJohn D. HerszmanMichael Berger

subject

010405 organic chemistryChemistryOrganic ChemistryHypervalent molecule010402 general chemistryElectrochemistry01 natural sciencesBiochemistryCombinatorial chemistry0104 chemical sciencesReagentPhysical and Theoretical ChemistrySelectivityStoichiometry

description

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.

yearjournalcountryeditionlanguage
2019-09-12Organic Letters
https://doi.org/10.1021/acs.orglett.9b02884