Angew. Chem. Int. Ed. [LASYROC]

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