Chalcogen-Bonding Catalysis with Telluronium Cations

Chalcogen bonding results from non-covalent interactions occurring between electrodeficient chalcogen atoms and Lewis bases. Among the chalcogens, tellurium is the strongest Lewis acid, but Te-based compounds are scarcely used as organocatalysts. For the first time, telluronium cations demonstrated impressive catalytic properties at low loadings in three benchmark reactions: the Friedel-Crafts bromination of anisole, the bromolactonization of omega-unsaturated carboxylic acids and the aza-Diels-Alder between Danishefsky's diene and imines. The ability of telluronium cations to interact with a Lewis base through chalcogen bonding was demonstrated on the basis of multi-nuclear (O-17, P-31, and Te-125) NMR analysis and DFT calculations.

Automated summary

Chalcogen bonding between telluronium cations and Lewis bases was shown to have impressive catalytic properties in benchmark reactions. The interaction was confirmed through multi-nuclear NMR analysis and DFT calculations, highlighting the potential of telluronium cations as organocatalysts.