TY - JOUR
T1 - Facile Synthesis of NH-Free 5-(Hetero)Aryl-Pyrrole-2-Carboxylates by Catalytic C–H Borylation and Suzuki Coupling
AU - Kanwal, Saba
AU - Ann, Noor-ul-
AU - Fatima, Saman
AU - Emwas, Abdul-Hamid M.
AU - Alazmi, Meshari
AU - Gao, Xin
AU - Ibrar, Maha
AU - Zaib Saleem, Rahman Shah
AU - Chotana, Ghayoor Abbas
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This 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.
PY - 2020/5/5
Y1 - 2020/5/5
N2 - 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.
AB - 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.
UR - http://hdl.handle.net/10754/662765
UR - https://www.mdpi.com/1420-3049/25/9/2106
UR - http://www.scopus.com/inward/record.url?scp=85084277481&partnerID=8YFLogxK
U2 - 10.3390/molecules25092106
DO - 10.3390/molecules25092106
M3 - Article
C2 - 32365945
SN - 1420-3049
VL - 25
SP - 2106
JO - Molecules
JF - Molecules
IS - 9
ER -