Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C-H Borylation and Suzuki Coupling

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2020 May 6

PMID 32365945

Citations 2

Authors

Saba Kanwal

Noor-Ul- Ann

Saman Fatima

Abdul-Hamid Emwas

Meshari Alazmi

Xin Gao

Maha Ibrar

Rahman Shah Zaib Saleem

Ghayoor Abbas Chotana

Affiliations

Soon will be listed here.

Abstract

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.

Citing Articles

Iridium-Catalyzed C-H Borylation of CF-Substituted Pyridines.

Shahzadi H, Fatima S, Akhter N, Alazmi M, Nawaf A, Said K ACS Omega. 2022; 7(13):11460-11472.

PMID: 35415379 PMC: 8992268. DOI: 10.1021/acsomega.2c00773.

Advances in Cross-Coupling Reactions.

Perez Sestelo J, Sarandeses L Molecules. 2020; 25(19).

PMID: 33019540 PMC: 7582370. DOI: 10.3390/molecules25194500.

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