Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling
Emwas, Abdul-Hamid M.
Zaib Saleem, Rahman Shah
Chotana, Ghayoor Abbas
KAUST DepartmentComputational Bioscience Research Center (CBRC)
Computer Science Program
Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division
Structural and Functional Bioinformatics Group
Permanent link to this recordhttp://hdl.handle.net/10754/662765
MetadataShow full item record
AbstractA 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.
CitationKanwal, S., Ann, N.-, Fatima, S., Emwas, A.-H., Alazmi, M., Gao, X., … Chotana, G. A. (2020). Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling. Molecules, 25(9), 2106. doi:10.3390/molecules25092106
SponsorsThis research was funded by HIGHER EDUCATION COMMISION OF PAKISTAN, grant number NRPU-4426, and by LAHORE UNIVERSITY OF MANAGEMENT SCIENCES through start-up and faculty initiative fund to G.A.C.
We extend our acknowledgement to KAUST core labs facilities for NMR and HRMS measurements.