One-Pot Synthesis of Tertiary Amides from Organic Trichlorides through Oxygen Atom Incorporation from Air by Convergent Paired Electrolysis
Zhongli Luo, Kenji Imamura, Yoshihito Shiota, Kazunari Yoshizawa, Yoshio Hisaeda, Hisashi Shimakoshi
Abstract
A convergent paired electrolysis catalyzed by a B12 complex for the one-pot synthesis of a tertiary amide from organic trichlorides (R-CCl3) has been developed. Various readily available organic trichlorides, such as benzotrichloride and its derivatives, chloroform, dichlorodiphenyltrichloroethane (DDT), trichloro-2,2,2-trifluoroethane (CFC-113a), and trichloroacetonitrile (CNCCl3), were converted to amides in the presence of tertiary amines through oxygen incorporation from air at room temperature. The amide formation mechanism in the paired electrolysis, which was mediated by a cobalt complex, was proposed.
Topics & Concepts
ChemistryElectrolysisAmideChloroformOxygenOxygen atomOrganic chemistryMedicinal chemistryInorganic chemistryMoleculeElectrodePhysical chemistryElectrolyteRadical Photochemical ReactionsChemical Synthesis and ReactionsSulfur-Based Synthesis Techniques