Electrochemical Aerobic Oxygenation and Nitrogenation of Cyclic Alkenes via C═C Bond Cleavage or Oxygenation and Azidation of Open-Chain Alkenes.

An efficient strategy involving electrochemical C═C double-bond cleavage and functionalization of cyclic alkenes for the synthesis of ketonitriles is described. This transformation features environmentally friendly conditions and utilizes relatively safe TMSN 3 as the nitrogenation reagent and molecular oxygen as the oxidant. For the open-chain alkenes, the reaction gave 1,2-difunctionalized products. A wide range of cyclic alkenes and open-chain alkenes were found to be compatible, providing the corresponding ketonitriles and α-azido aromatic ketones in moderate to good yields.