Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C-H Borylation and Suzuki Coupling.
2,3′-bipyrrole
5-aryl pyrrole-2-carboxylates
Borylation
NH-Free
Suzuki coupling
heteroaryl substituted pyrroles
iridium-catalyzed
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
30 Apr 2020
30 Apr 2020
Historique:
received:
11
04
2020
revised:
26
04
2020
accepted:
29
04
2020
entrez:
6
5
2020
pubmed:
6
5
2020
medline:
10
2
2021
Statut:
epublish
Résumé
A convenient two-step preparation of NH-free 5-aryl-pyrrole-2-carboxylates is described. The synthetic route consists of catalytic borylation of commercially available pyrrole-2-carboxylate ester followed by Suzuki coupling without going through pyrrole N-H protection and deprotection steps. The resulting 5-aryl substituted pyrrole-2-carboxylates were synthesized in good- to excellent yields. This synthetic route can tolerate a variety of functional groups including those with acidic protons on the aryl bromide coupling partner. This methodology is also applicable for cross-coupling with heteroaryl bromides to yield pyrrole-thiophene, pyrrole-pyridine, and 2,3'-bi-pyrrole based bi-heteroaryls.
Identifiants
pubmed: 32365945
pii: molecules25092106
doi: 10.3390/molecules25092106
pmc: PMC7248765
pii:
doi:
Substances chimiques
Pyrroles
0
2-pyrrolecarboxylic acid
634-97-9
Proline
9DLQ4CIU6V
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : HIGHER EDUCATION COMMISION OF PAKISTAN
ID : NRPU-4426
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