This study presents a TMSCN-enabled tandem reaction involving enamides and elemental selenium to access a diverse array of benzoselenophenes. Notably, this methodology involves the direct 2-fold C(sp2)-H bond activation without the need for preinstalled halides or boronic acids as reaction handles. The protocol offers several noteworthy features, including the absence of transition metals and strong oxidants, high reaction efficiency, broad substrate scopes, and the use of stable elemental selenium as a selenium source.