Chalcogen...π Bonding Catalysis

While the presence of sulfur...pi 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...pi bonding catalysis that activates molecules of pi systems through the interaction between chalcogen and pi-electron cloud. The proof-of-concept studies using a vinylindole-based Diels-Alder benchmark reaction demonstrate that S...pi and Se...pi bonding interaction can drive the cycloaddition reaction efficiently. Experimental results suggest that a simultaneously double Se...pi bonding interaction directs the stereoselectivity in this cycloaddition process.

Automated summary

This study introduces the concept of chalcogen...pi bonding catalysis, which activates molecules of pi systems through interaction between chalcogen and pi-electron cloud. The experimental results demonstrate that S...pi and Se...pi bonding interaction can efficiently drive the cycloaddition reaction, with double Se...pi bonding interaction influencing the stereoselectivity of the process.