Catalytic Activation of Imines by Chalcogen Bond Donors in a Povarov [4+2] Cycloaddition Reaction.
Lewis acids
chalcogen bonding
cycloaddition
non-covalent interactions
organocatalysis
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
22 Aug 2022
22 Aug 2022
Historique:
received:
12
04
2022
pubmed:
16
6
2022
medline:
25
8
2022
entrez:
15
6
2022
Statut:
ppublish
Résumé
Recently, chalcogen bonding has been investigated in more detail in organocatalysis and the scope of activated functionalities continues to increase. Herein, the activation of imines in a Povarov [4+2] cycloaddition reaction with bidentate cationic chalcogen bond donors is presented. Tellurium-based Lewis acids show superior properties compared to selenium-based catalysts and inactive sulfur-based analogues. The catalytic activity of the chalcogen bonding donors increases with weaker binding anions. Triflate, however, is not suitable due to its participation in the catalytic pathway. A solvent screening revealed a more efficient activation in less polar solvents and a pronounced effect of solvent (and catalyst) on endo : exo diastereomeric ratio. Finally, new chiral chalcogen bonding catalysts were applied but provided only racemic mixtures of the product.
Identifiants
pubmed: 35704037
doi: 10.1002/chem.202200917
pmc: PMC9545453
doi:
Substances chimiques
Imines
0
Solvents
0
Selenium
H6241UJ22B
Tellurium
NQA0O090ZJ
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200917Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : HU1782/5-1
Organisme : Deutsche Forschungsgemeinschaft
ID : EXC 2033 - 390677874
Organisme : European Regional Development Fund
Organisme : Ministerium für Innovation, Wissenschaft und Forschung des Landes Nordrhein-Westfalen
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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