Electrochemical Amidation: Benzoyl Hydrazine/Carbazate and Amine as Coupling Partners
Tipu Alam, Amitava Rakshit, Hirendra Nath Dhara, Angshuman Palai, Bhisma K. Patel
Abstract
An electrochemical amidation of benzoyl hydrazine/carbazate and primary/secondary amine as coupling partners via concomitant cleavage and formation of C(sp2)–N bonds has been achieved. This methodology proceeds under metal-free and exogenous oxidant-free conditions producing N2 and H2 as byproducts. Mechanistic studies reveal the in situ generations of both acyl and N-centered radicals from benzoyl hydrazines and amines. The utility of this protocol is demonstrated through a large-scale, and synthesis of bezafibrate, a hyperlipidemic drug.
Topics & Concepts
ChemistryAmine gas treatingHydrazine (antidepressant)ElectrochemistryCombinatorial chemistryPrimary (astronomy)RadicalOrganic chemistryElectrodeBiochemistryAstronomyPhysical chemistryPhysicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesChemical Synthesis and Analysis