Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling
Type
ArticleAuthors
Kanwal, SabaAnn, Noor-ul-
Fatima, Saman
Emwas, Abdul-Hamid M.

Alazmi, Meshari

Gao, Xin

Ibrar, Maha
Zaib Saleem, Rahman Shah

Chotana, Ghayoor Abbas

KAUST Department
Computational Bioscience Research Center (CBRC)Computer Science Program
Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division
NMR
Structural and Functional Bioinformatics Group
Date
2020-04-30Submitted Date
2020-04-11Permanent link to this record
http://hdl.handle.net/10754/662765
Metadata
Show full item recordAbstract
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.Citation
Kanwal, S., Ann, N.-, Fatima, S., Emwas, A.-H., Alazmi, M., Gao, X., … Chotana, G. A. (2020). Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling. Molecules, 25(9), 2106. doi:10.3390/molecules25092106Sponsors
This research was funded by HIGHER EDUCATION COMMISION OF PAKISTAN, grant number NRPU-4426, and by LAHORE UNIVERSITY OF MANAGEMENT SCIENCES through start-up and faculty initiative fund to G.A.C.We extend our acknowledgement to KAUST core labs facilities for NMR and HRMS measurements.
Publisher
MDPI AGJournal
MoleculesPubMed ID
32365945Additional Links
https://www.mdpi.com/1420-3049/25/9/2106https://www.mdpi.com/1420-3049/25/9/2106/pdf
ae974a485f413a2113503eed53cd6c53
10.3390/molecules25092106
Scopus Count
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