Helquats as Promoters of the Povarov Reaction: Synthesis of 1,2,3,4-Tetrahydroquinoline Scaffolds Catalyzed by Helicene-Viologen Hybrids.
Povarov reaction
electron transfer
helquats
radicals
tetrahydroquinolines
Journal
ChemPlusChem
ISSN: 2192-6506
Titre abrégé: Chempluschem
Pays: Germany
ID NLM: 101580948
Informations de publication
Date de publication:
10 2020
10 2020
Historique:
received:
28
02
2020
revised:
29
04
2020
pubmed:
14
5
2020
medline:
16
6
2021
entrez:
14
5
2020
Statut:
ppublish
Résumé
Helquats (HQs) are structurally linked to helicenes and viologens, and they represent an attractive field of research in chemistry and medicinal chemistry. In the present work they were used as catalysts for the synthesis of 1,2,3,4-tetrahydroquinolines in good yields by the Povarov reaction. The substrate scope and the capability of different helquats to promote Povarov reactions are demonstrated. Studies to elucidate mechanistic details revealed that helquats act as single-electron transfer oxidants through a cation-radical mechanism. The screening of the catalytic activity of HQs confirmed that an active HQ must have a LUMO energy below -8.67 eV and the standard redox potential higher (less negative) than -1.2 V vs. the ferrocene/ferrocenium redox couple.
Identifiants
pubmed: 32400944
doi: 10.1002/cplu.202000151
doi:
Substances chimiques
Polycyclic Compounds
0
Quinolines
0
Viologens
0
helicenes
0
1,2,3,4-tetrahydroquinoline
CCR50N1Z9G
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2212-2218Subventions
Organisme : Academy of Sciences of the Czech Republic
ID : 61388963
Organisme : Academy of Sciences of the Czech Republic
ID : 61388955
Organisme : Czech Grant Agency
ID : 20-03691X
Organisme : IOCB
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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