6533b7dcfe1ef96bd12721a9

RESEARCH PRODUCT

Electrochemical Fluorocyclization of N-Allylcarboxamides to 2-Oxazolines by Hypervalent Iodine Mediator

Siegfried R. WaldvogelJohn D HauptMichael Berger

subject

010405 organic chemistryAnodic oxidationResource savingOrganic ChemistryHypervalent moleculechemistry.chemical_element010402 general chemistryIodineElectrochemistry01 natural sciencesBiochemistryCombinatorial chemistry0104 chemical scienceschemistryReagentPhysical and Theoretical Chemistry

description

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·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.

yearjournalcountryeditionlanguage
2018-12-18Organic Letters
https://doi.org/10.1021/acs.orglett.8b03682