Manganese-Catalyzed Electrochemical Tandem Azidation–Coarctate Reaction: Easy Access to 2-Azo-benzonitriles
Debabrata Maiti, Kingshuk Mahanty, Suman De Sarkar
Abstract
A one-pot cascade transformation consisting of an electrochemically driven azidation of 2 H -indazole followed by coarctate fragmentation is developed to synthesize the 2-azo-benzonitrile motif. This manganese-catalyzed transformation is external-chemical-oxidant-free and operates at ambient temperature under air. This methodology exhibits good functional group tolerance, affording a broad range of substrate scopes of up to 89% isolated yield. Diverse derivatization of the 2-azo-benzonitrile product resulted in other valuable scaffolds.
Topics & Concepts
ChemistryBenzonitrileIndazoleCatalysisCombinatorial chemistryTandemManganeseCascade reactionDerivatizationReagentElectrochemistryYield (engineering)Organic chemistryMaterials scienceMetallurgyPhysical chemistryHigh-performance liquid chromatographyElectrodeComposite materialRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques