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.
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.
Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. mphahmj@unisa.ac.za
Malose Jack
MJ
Mphahlele
Mamasegare Mabel
MM
Mphahlele
D000818:Animals; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*
D001897:Boronic Acids; D011804:Quinolines; C032391:palladium hydride; D010165:Palladium