Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.
Catalysis
Dearomatisation
Isoquinolines
Quinolines
Reduction
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:
04 07 2022
04 07 2022
Historique:
received:
30
03
2022
pubmed:
14
5
2022
medline:
30
6
2022
entrez:
13
5
2022
Statut:
ppublish
Résumé
Herein we disclose a mild protocol for the reductive functionalisation of quinolinium and isoquinolinium salts. The reaction proceeds under transition-metal-free conditions as well as under rhodium catalysis with very low catalyst loadings (0.01 mol %) and uses inexpensive formic acid as the terminal reductant. A wide range of electrophiles, including enones, imides, unsaturated esters and sulfones, β-nitro styrenes and aldehydes are intercepted by the in situ formed enamine species forming a large variety of substituted tetrahydro(iso)quinolines. Electrophiles are incorporated at the C-3 and C-4 position for quinolines and isoquinolines respectively, providing access to substitution patterns which are not favoured in electrophilic or nucleophilic aromatic substitution. Finally, this reactivity was exploited to facilitate three types of annulation reactions, giving rise to complex polycyclic products of a formal [3+3] or [4+2] cycloaddition.
Identifiants
pubmed: 35560761
doi: 10.1002/anie.202204682
pmc: PMC9321684
doi:
Substances chimiques
Isoquinolines
0
Quinolines
0
Rhodium
DMK383DSAC
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202204682Subventions
Organisme : Austrian Science Fund FWF
ID : J 4483
Pays : Austria
Informations de copyright
© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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