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

• Main Authors: Mamasegare Mabel Mphahlele, Malose Jack Mphahlele
• Format: Article
• Language: English
• Published: MDPI AG 2011-10-01
• Series: Molecules
• Subjects: 2-aryl-4-azido-3-iodoquinolines; Suzuki-Miyaura cross-coupling; symmetrical biaryls; 4-azido-2,3-diarylquinolines; 4-amino-2,3-diarylquinolines
• Online Access: http://www.mdpi.com/1420-3049/16/11/8958/
• ISSN: 1420-3049

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.