Chelate-assisted direct selenation of aryl C-H bonds with diselenides catalyzed by palladium.

A direct selenation of inert C-H bonds of benzamide derivatives and their related compounds with diselenides has been achieved with the palladium catalyst. The reaction was compatible with a variety of functional groups, including a bromo group. Primitive mechanistic insights revealed that the reaction proceeded through a C-H bond cleavage and the sequential oxidative addition of diselenides. The present synthetic method can be applied to the facile synthesis of selenoxanthone which can be regarded as promising heterocyclic materials.