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Molecules ; 25(9)2020 Apr 30.
Article in English | MEDLINE | ID: mdl-32365945

ABSTRACT

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.


Subject(s)
Chemistry Techniques, Synthetic , Oxidative Coupling , Proline/analogs & derivatives , Catalysis , Cyclization , Molecular Structure , Proline/chemical synthesis , Proline/chemistry , Pyrroles/chemistry
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