A new electrochemical strategy for the synthesis of a new type of sulfonamide derivatives

This study is the first report of electrochemical generation of hydroxyimino-cyclohexa-dien-ylidene haloniums and their application in the synthesis of new halo-N-hydroxysulfonamide derivatives. These compounds were obtained in a one-pot process based on the reaction of halonium acceptors with arylsulfinic acids. The method is easy to carry out, as it is performed using the carbon electrodes in a simple undivided cell. The protocol has a broad substrate scope with a tolerance for a variety of functional groups. The proposed mechanism is a ping-pong type reaction mechanism, which in its first stage the halonitroarene is reduced at the cathode to related hydroxylamine and in the second stage the cathodically generated hydroxylamine by oxidation at the anode and participating in disproportionation reaction is converted to the halonium acceptor.