Chalcogen-Bonding Catalysis with Telluronium Cations.
Lewis acids
chalcogen bonding
non-covalent interactions
organocatalysis
tellurium
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
23 Aug 2021
23 Aug 2021
Historique:
revised:
04
06
2021
received:
22
04
2021
pubmed:
25
6
2021
medline:
25
6
2021
entrez:
24
6
2021
Statut:
ppublish
Résumé
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 (
Identifiants
pubmed: 34166563
doi: 10.1002/anie.202105482
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
19281-19286Subventions
Organisme : LabEx Chimie des Systèmes Complexes
ID : ANR-10-LABX-0026 CSC
Informations de copyright
© 2021 Wiley-VCH GmbH.
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Notes added in proofs: Two elegant publications appeared online while this one was submitted: one reported the synthesis of bis-telluronium derivatives with increased anion binding ability, and their use as cocatalyst in Au- or Pt-catalyzed cycloisomerization; see B. Zhou, F. Gabbai, J. Am. Chem. Soc. 2021, 143, 8625-8630; the other reported the synthesis of mixed telluride/telluronium cations and telluroniums similar to those reported here and their application as catalysts for the hydrogenation of 2-phenyl-quinoline with Hantzsch ester; see:
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