Electrochemical Synthesis of Cyanoformamides from Trichloroacetonitrile and Secondary Amines Mediated by the B<sub>12</sub> Derivative
Mohammad Moniruzzaman, Yoshio Yano, Toshikazu Ono, Kenji Imamura, Yoshihito Shiota, Kazunari Yoshizawa, Yoshio Hisaeda, Hisashi Shimakoshi
Abstract
The B12 derivative, heptamethyl cobyrinate, -mediated electrochemical synthesis of cyanoformamides has been developed. Aerobic oxygenation of the carbon-centered radical initiated in situ generation of the reactive acyl chloride intermediate, which led to cyanoformamides in the presence of an amine. This one-pot and scalable synthetic method has been demonstrated with 41 examples up to 94% yields with 21 new compounds. The mechanism of electrolysis mediated by the B12 derivative has been proposed based on the DFT calculations.
Topics & Concepts
ChemistryDerivative (finance)ElectrolysisElectrochemistryAmine gas treatingBulk electrolysisReaction mechanismChlorideCombinatorial chemistryPhotochemistryMedicinal chemistryOrganic chemistryCyclic voltammetryCatalysisElectrodePhysical chemistryElectrolyteEconomicsFinancial economicsCO2 Reduction Techniques and CatalystsRadical Photochemical ReactionsAdvanced battery technologies research