Entropy-Induced Selectivity Switch in Gold Catalysis: Fast Access to Indolo[1,2-a]quinolines.
gold catalysis
material science
nitrogen heterocycles
photophysics
selectivity switch
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
04 Oct 2022
04 Oct 2022
Historique:
received:
13
06
2022
pubmed:
15
6
2022
medline:
12
10
2022
entrez:
14
6
2022
Statut:
ppublish
Résumé
New N-heterocyclic compounds for organic functional materials and their efficient syntheses are highly demanded. A surprising entropy-induced selectivity switch in the gold-catalyzed intramolecular hydroarylation of 2-ethynyl N-aryl indoles was found and its exploitation led to straightforward syntheses of indolo[1,2-a]quinolines. Experimental and computational mechanistic investigations gave insight into this uncommon selectivity phenomenon and into the special reactivity of the indolo[1,2-a]quinolines. The high functional group tolerance of this methodology enabled access to a diverse scope with high yields. In addition, bidirectional approaches, post-functionalization reactions, and π-extension of the core structure were feasible. An in-depth study of the photophysical properties explored the structure-effect relationship for different derivatives and revealed a high potential of these compounds for future applications as functional materials.
Identifiants
pubmed: 35699266
doi: 10.1002/chem.202201816
doi:
Substances chimiques
Heterocyclic Compounds
0
Indoles
0
Quinolines
0
Gold
7440-57-5
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202201816Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB 1249
Organisme : Alexander von Humboldt-Stiftung
ID : Feodor Lynen research fellowship
Organisme : Institute for Basic Science
ID : IBS-R10-A1
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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