Polychlorinated alkylation annulation of N-arylacrylamide under electrochemical conditions†
Abstract
A novel and unprecedented method for the polychlorinated alkylation annulation of N-arylacrylamide has been developed under electrochemical conditions with diazo salt as the mediator at the cathode reduction and CH2Cl2 as the substrate and solvent. Remarkably, it is benzene free radicals generated from the diazo salt under reductive electrolytic conditions that induce the hydrogen transfer of CH2Cl2, resulting in the formation of polychloromethyl radicals, which were transferred into the bulk phase solution and then reacted with the N-arylacrylamide substrate. This electrochemical diazo-salt-mediated protocol provides a broad range of functional tolerance and affords good yields for polychloromethyl indolone derivatives under ambient conditions at room temperature in a simple undivided cell.