Chalcogen-Bonding Catalysis with Telluronium Cations.

Authors :: Weiss R
Aubert E
Pale P
Mamane V
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2021 Aug 23; Vol. 60 (35), pp. 19281-19286. Date of Electronic Publication: 2021 Jul 20.
Publication Year :: 2021
Abstract: 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 ω-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 ( <superscript>17</superscript> O, <superscript>31</superscript> P, and <superscript>125</superscript> Te) NMR analysis and DFT calculations.<br /> (© 2021 Wiley-VCH GmbH.)