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Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling
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 res...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248765/ https://www.ncbi.nlm.nih.gov/pubmed/32365945 http://dx.doi.org/10.3390/molecules25092106 |
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author | Kanwal, Saba Ann, Noor-ul- Fatima, Saman Emwas, Abdul-Hamid Alazmi, Meshari Gao, Xin Ibrar, Maha Zaib Saleem, Rahman Shah Chotana, Ghayoor Abbas |
author_facet | Kanwal, Saba Ann, Noor-ul- Fatima, Saman Emwas, Abdul-Hamid Alazmi, Meshari Gao, Xin Ibrar, Maha Zaib Saleem, Rahman Shah Chotana, Ghayoor Abbas |
author_sort | Kanwal, Saba |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7248765 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-72487652020-08-13 Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling Kanwal, Saba Ann, Noor-ul- Fatima, Saman Emwas, Abdul-Hamid Alazmi, Meshari Gao, Xin Ibrar, Maha Zaib Saleem, Rahman Shah Chotana, Ghayoor Abbas Molecules Article 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. MDPI 2020-04-30 /pmc/articles/PMC7248765/ /pubmed/32365945 http://dx.doi.org/10.3390/molecules25092106 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Kanwal, Saba Ann, Noor-ul- Fatima, Saman Emwas, Abdul-Hamid Alazmi, Meshari Gao, Xin Ibrar, Maha Zaib Saleem, Rahman Shah Chotana, Ghayoor Abbas Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling |
title | Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling |
title_full | Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling |
title_fullStr | Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling |
title_full_unstemmed | Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling |
title_short | Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling |
title_sort | facile synthesis of nh-free 5-(hetero)aryl-pyrrole-2-carboxylates by catalytic c–h borylation and suzuki coupling |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248765/ https://www.ncbi.nlm.nih.gov/pubmed/32365945 http://dx.doi.org/10.3390/molecules25092106 |
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