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Electrochemical Intramolecular Oxytrifluoromethylation of <i>N</i>-Tethered Alkenyl Alcohols: Synthesis of Functionalized Morpholines

Aurélie Claraz, Thibaut Courant, Géraldine Masson

2020Organic Letters68 citationsDOIOpen Access PDF

Abstract

An electrochemical intramolecular oxytrifluoromethylation of N-tethered alkenyl alcohols was developed providing straightforward access to CF3-containing morpholines derivatives. The method features mild reaction conditions with direct anodic oxidation of Langlois reagent as a cheap and easy to handle trifluoromethylating reagent. Variously substituted 2-(2,2,2-trifluoroethyl)morpholines were obtained in moderate to high yields under constant current electrolysis in an undivided cell.

Topics & Concepts

ChemistryIntramolecular forceReagentElectrochemistryElectrolysisAnodeCombinatorial chemistryOrganic chemistryElectrodePhysical chemistryElectrolyteFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques