Journal
ORGANIC LETTERS
Volume 21, Issue 19, Pages 7893-7896Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02884
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Funding
- Friedrich Ebert Foundation
- Carl Zeiss Foundation for the research network ELYSION
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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 center dot 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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