Direct one-pot synthesis of primary 4-amino-2,3-diarylquinolines via Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodoquinolines with arylboronic acids

Abstract

Palladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3- iodoquinolines 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. © 2011 by the authors; licensee MDPI, Basel, Switzerland.