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Open AccessArticle

An Efficient Synthesis of Aryl-Substituted Pyrroles by the Suzuki–Miyaura Coupling Reaction of SEM-Protected Pyrroles

1
College of Life Science and Bio-engineering, Beijing University of Technology, 100 Ping Le Yuan, Chaoyang District, Beijing 100124, China
2
State Key Laboratory of Bioactive Substances and Function of Natural Medicine, Beijing Key Laboratory of Active Substance Discovery and Druggability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, 1 Xian Nong Tan Street, Beijing 100050, China
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(8), 1594; https://doi.org/10.3390/molecules24081594
Received: 19 March 2019 / Revised: 5 April 2019 / Accepted: 20 April 2019 / Published: 22 April 2019
(This article belongs to the Section Organic Chemistry)
An efficient arylation of SEM-protected pyrroles by the Suzuki–Miyaura coupling reaction has been developed. The reaction can be carried out under mild conditions to provide aryl-substituted pyrroles in moderate to excellent yields. The scope and limitations of the methodology were evaluated, and the reaction was tolerant of a wide range of functionalities. Compared to the reported methods, the protocol has some advantages, such as commercially available materials, no debrominated by-products being formed, and the amine-protecting group being stable under the reaction conditions. The synthetic utility of the product has also been demonstrated, with several common transformations of the aryl-substituted pyrrole product being conducted. This protocol will offer the opportunity to explore other metal-catalyzed cross-coupling reactions employing SEM-protected pyrroles. View Full-Text
Keywords: aryl-substituted pyrroles; Suzuki–Miyaura coupling reaction; SEM-protected pyrroles aryl-substituted pyrroles; Suzuki–Miyaura coupling reaction; SEM-protected pyrroles
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MDPI and ACS Style

Cui, K.; Gao, M.; Zhao, H.; Zhang, D.; Yan, H.; Huang, H. An Efficient Synthesis of Aryl-Substituted Pyrroles by the Suzuki–Miyaura Coupling Reaction of SEM-Protected Pyrroles. Molecules 2019, 24, 1594.

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