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

Saba Kanwal, Noor-ul- Ann, Saman Fatima, Abdul-Hamid M. Emwas, Meshari Alazmi, Xin Gao, Maha Ibrar, Rahman Shah Zaib Saleem, Ghayoor Abbas Chotana

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)2106
JournalMolecules
Volume25
Issue number9
DOIs
StatePublished - May 5 2020

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