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

Molecules

Meshari Alazmi¹  Xin Gao¹  Abdul-Hamid Emwas²  Noor-ul- Ann³  RahmanShah Zaib Saleem³  Saba Kanwal³  Saman Fatima³  GhayoorAbbas Chotana³  Maha Ibrar³ 

[1] Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division, Computational Bioscience Research Center (CBRC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia;Core Labs, King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia;Department of Chemistry and Chemical Engineering, Syed Babar Ali School of Science & Engineering (SBASSE), Lahore University of Management Sciences (LUMS), Lahore 54792, Pakistan;

关键词: Borylation;    Suzuki coupling;    NH-Free;    5-aryl pyrrole-2-carboxylates;    iridium-catalyzed;    heteroaryl substituted pyrroles;   

DOI  :  10.3390/molecules25092106

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown