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A highly efficient and aerobic protocol for the synthesis of N-heteroaryl substituted 9-arylcarbazolyl derivatives via a palladium-catalyzed ligand-free Suzuki reaction

Release Time:2019-03-09  Hits:

Indexed by: Journal Article

Date of Publication: 2012-10-21

Journal: ORGANIC & BIOMOLECULAR CHEMISTRY

Included Journals: Scopus、PubMed、EI、SCIE

Volume: 10

Issue: 39

Page Number: 7875-7883

ISSN: 1477-0520

Abstract: A palladium-catalyzed aerobic and ligand-free Suzuki reaction in aqueous ethanol has been developed for the synthesis of N-heteroaryl substituted 9-arylcarbazolyl derivatives. A number of N-heteroaryl halides, namely 2-halogenated pyridines, 2-bromoquinoline, 5-bromopyrimidine and 2-chloropyrazine, were coupled with 4-(9H-carbazol-9-yl)phenylboronic acid (CPBA) or 9-phenyl-9H-carbazol-3-ylboronic acid (PCBA) efficiently to afford good to excellent yields in a short reaction time. Moreover, the catalytic system of Pd(OAc)(2)-EtOH/H2O-K2CO3 was successfully extended to the cross-couplings of N-heteroaryl halides with various arylboronic acids. The results demonstrated that the cross-coupling reaction in the present protocol was promoted by oxygen.

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