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Molecules 2011, 16(11), 8958-8972; doi:10.3390/molecules16118958
Article

Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids

*  and
Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa
* Author to whom correspondence should be addressed.
Received: 30 September 2011 / Revised: 20 October 2011 / Accepted: 21 October 2011 / Published: 25 October 2011
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Abstract

Palladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodo-quinolines with arylboronic acids afforded the corresponding primary 4-amino-2,3-diarylquinolines in a single-pot operation along with symmetrical biaryls and traces of the 2,3-diaryl-4-azidoquinolines. A plausible mechanism, which implicates palladium hydride species in the reduction of the incipient 2,3-diaryl-4-azidoquinolines to afford the 4-amino-2,3-diarylquinolines is proposed.
Keywords: 2-aryl-4-azido-3-iodoquinolines; Suzuki-Miyaura cross-coupling; symmetrical biaryls; 4-azido-2,3-diarylquinolines; 4-amino-2,3-diarylquinolines 2-aryl-4-azido-3-iodoquinolines; Suzuki-Miyaura cross-coupling; symmetrical biaryls; 4-azido-2,3-diarylquinolines; 4-amino-2,3-diarylquinolines
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Mphahlele, M.J.; Mphahlele, M.M. Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids. Molecules 2011, 16, 8958-8972.

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