Electrochemical Nickel-Catalyzed Synthesis of Unsymmetrical Diorganyl Selanes from Diaryl Diselanes and Aryl and Alkyl Iodides

The synthesis of unsymmetrical diorganyl selanes was accomplished under electrochemical conditions in an undivided cell utilizing a magnesium cathode and a carbon anode made out of aryl and alkyl iodides and diselanes. This electrochemical cross-electrophile coupling (eXEC) was accomplished using a simple nickel catalyst formed in situ out of Ni(acac)2 and 2,2'-bipyridine in DMF at ambient temperatures. The reaction showed good functional group compatibility, and heteroaryl iodides, such as thiophene or pyridine derivatives, were well accepted.