Electrochemical Intramolecular Oxytrifluoromethylation of N -Tethered Alkenyl Alcohols: Synthesis of Functionalized Morpholines

Aurélie Claraz (1) , Thibaut Courant (1) , Geraldine Masson (1)

1 ICSN - Institut de Chimie des Substances Naturelles

An electrochemical intramolecular oxytrifluoromethylation of N-tethered alkenyl alcohols was developed providing straightforward access to CF3-containg morpholines derivatives. The method features mild reaction conditions with direct anodic oxidation of Langlois reagent as 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.

Domaines: Chimie organique

Aurélie Claraz, Thibaut Courant, Geraldine Masson. Electrochemical Intramolecular Oxytrifluoromethylation of N -Tethered Alkenyl Alcohols: Synthesis of Functionalized Morpholines. Organic Letters, 2020, 22 (4), pp.1580-1584. ⟨10.1021/acs.orglett.0c00176⟩. ⟨hal-03058500⟩