Angew. Chem. Int. Ed.

Abstract

Chalcogen bonding results from non-covalent interaction 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 organocatalyst. For the first time, telluronium cations demonstrated impressive catalytic property at low loading 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 ( 17 O, 31 P and 125 Te) NMR analysis and DFT calculations.

Reference

Robin Weiss, Emmanuel Aubert, Patrick H. R. Pale, Victor Mamane
Chalcogen Bonding Catalysis with Telluronium Cations
Angew. Chem. Int. Ed., First published: 24 June 2021-DOI: https://doi.org/10.1002/anie.202105482

Contacts

V. Mamane and P. Pale, équipe LASYROC, Institut de Chimie (UMR 7177).

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This publication is part of a series of publications that you will find bellow:

P. Peluso, A. Dessì, R. Dallocchio, B. Sechi, C. Gatti, B. Chankvetadze, V. Mamane, R. Weiss, P. Pale, E. Aubert, S. Cossu
Enantioseparation of 5,5'-dibromo-2,2'-dichloro-3-selanyl-4,4'-bipyridines on poly-saccharide-based chiral stationary phases: exploring chalcogen bonds in liquid-phase chromatography.
Molecules (special issue, invited) 2021, 26, 221-238 - DOI: https://www.mdpi.com/1420-3049/26/1/221

A. Dessì; R. Dallocchio; R. Weiss; G. Andreotti; M. Allocca; E. Aubert; P. Pale; V. Mamane; S. Cossu, P. Peluso
Rational design, synthesis, characterization and evaluation of iodinated 4,4'-bipyridines as new transthyretin fibrillogenesis inhibitors
Molecules 2020, 25, 2213-2234 – DOI : https://www.mdpi.com/1420-3049/25/9/2213

V. Mamane, P. Peluso, E. Aubert, E. Wenger, S. Cossu, P. Pale
Disubstituted ferrocenyl iodo- and chalcogeno-alkynes as chiral halogen and chalcogen bond donors.
Organometallics 2020, 39, 3936-3960 – DOI : https://pubs.acs.org/doi/10.1021/acs.organomet.0c00633

R. Weiss, E. Aubert, P. Peluso, S. Cossu, P. Pale, V. Mamane
Chiral chalcogen bond donors based on the 4,4'-bipyridine scaffold
Molecules (special issue, Editor) 2019, 24, 4484 – DOI : https://www.mdpi.com/1420-3049/24/24/4484