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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

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Indexed by:期刊论文

Date of Publication:2012-10-21

Journal:ORGANIC & BIOMOLECULAR CHEMISTRY

Included Journals:SCIE、EI、PubMed、Scopus

Volume:10

Issue:39

Page Number:7875-7883

ISSN No.: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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