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Full Paper
One-Pot Synthesis of Furo- or Thienoquinolines through Sequential Imination and Intramolecular Palladium-Catalyzed Direct Arylation
Article first published online: 25 OCT 2012
DOI: 10.1002/ejoc.201201142
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Beydoun, K. and Doucet, H. (2012), One-Pot Synthesis of Furo- or Thienoquinolines through Sequential Imination and Intramolecular Palladium-Catalyzed Direct Arylation. Eur. J. Org. Chem., 2012: 6745–6751. doi: 10.1002/ejoc.201201142
Publication History
- Issue published online: 20 NOV 2012
- Article first published online: 25 OCT 2012
- Manuscript Received: 21 AUG 2012
Keywords:
- Synthetic methods;
- Heterocycles;
- Fused-ring systems;
- Homogeneous catalysis;
- Palladium;
- P ligands;
- C–H functionalization
Abstract
The sequential imination and intramolecular palladium-catalyzed direct arylation of thiophene-3-carbaldehyde or furan-3-carbaldehyde with 2-haloanilines provided a one-pot access to furo- or thienoquinolines in high yields with H2O and HBr as the major waste. Both electron-withdrawing and -donating substituents on the 2-haloaniline derivatives were tolerated. These furo- or thienoquinoline derivatives can be employed in the direct arylation at C-5 of the furyl or thienyl moiety, and a variety of corresponding arylation products were obtained in high yields.