Chalcogen-Bond Catalysis: Telluronium-Catalyzed [4+2]-Cyclocondensation of (in situ Generated) Aryl Imines with Alkenes.
chalcogen bonds
cycloaddition
organocatalysis
tellurium
σ-holes
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
13 Mar 2023
13 Mar 2023
Historique:
received:
31
10
2022
pubmed:
17
12
2022
medline:
17
12
2022
entrez:
16
12
2022
Statut:
ppublish
Résumé
In the chalcogen series, tellurium species exhibit the strongest chalcogen bonding (ChB) interaction with electron-rich atom. This property explains the renewed interested toward tellurium-based derivatives and their use in different applications, such as organocatalysis. In this context, the catalytic activity of telluronium salts in the Povarov reaction is presented herein. Different dienophiles, as well as imines of variable electronic nature, efficiently react in the presence of catalytic amount of either diarylmethyltelluronium or triaryltelluronium salts. Both catalysts could also readily perform the three-component Povarov reaction starting from aldehyde, aniline and dihydrofuran. The reactivity of telluroniums towards imines and aldehydes was confirmed in the solid state by the ability of Te atom to interact through ChB with the oxygen carbonyl of acetone, and in solution with significant shift variations of the imine proton and of the tellurium atom in
Identifiants
pubmed: 36524743
doi: 10.1002/chem.202203372
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202203372Subventions
Organisme : Fondation Pour la Recherche en Chimie
ID : ANR-10-LABX-0026 CSC
Organisme : Agence Nationale de la Recherche
ID : ANR-21-CE07-0014
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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