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

doi:10.3390/molecules16118958

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

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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

Malose Jack Mphahlele* and Mamasegare Mabel Mphahlele

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; in revised form: 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

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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.

AMA Style

Mphahlele MJ, Mphahlele MM. 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(11):8958-8972.

Chicago/Turabian Style

Mphahlele, Malose Jack; Mphahlele, Mamasegare Mabel. 2011. "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 16, no. 11: 8958-8972.

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