Synthesis, Structural Analysis and Catalytic Activity of Stabilized Selenenyl Halides From the Reaction of 1,2‍‐Benzisoselenazoles With Carbon Electrophiles

The synthesis of selenenyl halides stabilized by chalcogen bonding was accomplished by the reaction of benzisoselenazoles with a variety of carbon electrophiles under thermal activation. The X‐ray structures of five of these derivatives resulting from the oxidative addition of the carbon–halogen bond exhibited a stabilization by a Se–N interaction. These selenenyl halides react with organomagnesium reagents by substitution at the selenium center delivering a diarylselenide. The peroxidase and oxidase activities of the stabilized selenenyl halides were measured by UV–visible spectroscopy demonstrating the strong influence of the nitrogen substituent on the catalytic activities.