Journal
ORGANIC LETTERS
Volume 21, Issue 1, Pages 242-245Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03682
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Funding
- Friedrich Ebert Foundation
- Carl Zeiss Foundation for the research network ELYSION
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A resource saving protocol for the synthesis of 5-fluoromethyl-2-oxazolines by using electrochemistry has been realized. Thereby, a hypervalent iodine species I(III) is generated by anodic oxidation in the presence of Et3N center dot 5HF and mediates the cyclization of N-allylcarboxamide to 5-fluoromethyl-2-oxazoline. This method allows application to various substrates furnishing the 2-oxazolines with yields up to 68%. The protocol is easy to conduct under constant current conditions offering a sustainable alternative over conventional reagent-based pathways.
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