Abstract Chalcogen bonding catalysis with divalent chalcogenides required using heteroatoms as electron donors to give reactivity, while the activation of hydrocarbons such as alkenes by this concept remains an unresolved challenge. Herein, we discovered a powerful selenide catalyst that showed unprecedented capability in the activation of alkenes. The Se???π interactions were capable of catalyzing a broad range of transformations, including intermolecular cyclization and coupling reactions. Significantly, the Se???π bonding activation mode can be exploited to achieve intermolecular enyne cyclizations and controlled cross‐coupling of triple alkenes. The activation of alkenes by divalent selenides opens up a new avenue for supramolecular catalysis.
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