Hypervalent Chalcogenonium•••π Bonding Catalysis

A proof-of-concept study of hypervalent chalcogenonium center dot center dot center dot pi bonding catalysis was performed. A new catalytic strategy using 1,2-oxaselenolium salts as chalcogen bond donors and alkenes as chalcogen bond acceptors is described. The feasibility of this concept is demonstrated by the use of trisubstituted selenonium salts in the metal-free catalytic hydrofunctionalization and polymerization of alkenes via unconventional seleniranium ion-like intermediates. The results indicate that counter anions have a significant effect on the catalysis based on hypervalent chalcogenonium center dot center dot center dot pi bonding interactions.

Automated summary

This study presents a proof-of-concept for hypervalent chalcogenonium center dot center dot center dot pi bonding catalysis. A new catalytic strategy using 1,2-oxaselenolium salts as chalcogen bond donors and alkenes as chalcogen bond acceptors is described. The results demonstrate the feasibility of this concept and highlight the significant effect of counter anions on catalysis based on hypervalent chalcogenonium center dot center dot center dot pi bonding interactions.