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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
(This article belongs to the Section Organic Synthesis)
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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 (CC BY 3.0).
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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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