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While the presence of sulfur⋅⋅⋅π bonding interaction is a general phenomenon in the biological systems, the exploitation of this noncovalent force in a chemical process yet remains elusive. Herein, we describe the concept of chalcogen⋅⋅⋅π bonding catalysis that activates molecules of π systems through the interaction between chalcogen and π-electron cloud. The proof-of-concept studies using a vinylindole-based Diels-Alder benchmark reaction demonstrate that S⋅⋅⋅π and Se⋅⋅⋅π bonding interaction can drive the cycloaddition reaction effici
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