One-pot palladium-catalyzed C–I and C–H bond activation and subsequent Suzuki–Miyaura cross-coupling of 2-aryl-3-iodo-4-(phenylamino)quinolines with arylboronic acids

Pd(η3-1-PhC3H4)(η5-C5H5), an Unusually Effective Catalyst Precursor for Suzuki–Miyaura Cross-Coupling Reactions Catalyzed by Bis-Phosphine Palladium(0) Compounds

“…A second advantage of the use of Vb is that the Pd(0) products PdL 2 are formed under rigorously anhydrous conditions. The potential benefits of carrying out cross-coupling chemistry in the absence of water have been noted previously …”

Metal Catalyzed Suzuki-Miyaura Cross-Coupling– Efficient Methodology for Synthesis the Natural and non-Natural biological active Molecules

“…A plausible mechanism, which implicates a six-membered palladacycle intermediate is proposed for the formation of the observed mixture of products. The prepared compounds were characterized using a combination of spectroscopic and X-ray crystallographic techniques [19].…”

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

“…The 4-(2-methylphenylamino)-3-iodo-quinolines, for example, were previously subjected to palladium-catalyzed Heck reaction with terminal alkenes to afford the corresponding 3-vinylquinolines with gastric H + /K + -ATPase inhibitory activity [ 16 ]. On the other hand, the analogous 2-aryl-3-iodo-4-(phenylamino)quinolines were found to undergo one-pot palladium mediated C–I and C–H bond activation and subsequent Suzuki-Miyaura cross-coupling with arylboronic acids to afford mixtures of the 2,3-diaryl-4-(phenylamino)quinolines and 2-aryl-4-([(1,1'-biaryl)-2-yl]amino)quinoline derivatives [ 17 ]. Hitherto this investigation, the Staudinger reaction of 2-aryl-4-azido-3-halogenoquinolines (X = Br, I) with triphenylphosphine in refluxing tetrahydrofuran afforded the corresponding 2-aryl-3-halogeno-4-(triphenylphosphoran-ylideneamino)quinolines [ 18 ].…”