94878-29-2

Upstream product

• 98-86-2 acetophenone 
• 20712-12-3 (2-amino-5-bromophenyl)methanol 
• 98-80-6 phenylboronic acid 
• 3894-25-5 6-bromo-2-phenyl-quinoline 
• 29124-57-0 2-amino-5-bromobenzaldehyde 
• 300-57-2 allylbenzene 
• 92-67-1 4-phenylalanine 
• 104-54-1 3-Phenylpropenol 
• 612-95-3 6-phenylquinoline 
• 100-59-4 phenylmagnesium chloride 

Relevant academic research and scientific papers

Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes

The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.

Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines

A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described. This process works in the absence of acid, base and any other additive and has a broad substrate scope, tolerating electron-withdrawing groups such as nitryl, trifluoromethyl and so on. A series of quinolines are prepared in satisfactory yields.

Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives

An efficient and practical palladium-catalyzed aerobic oxidative approach to afford functionalized 2-substituted quinolines in moderate to good yields from readily available allylbenzenes with aniline is developed. The present annulation process has high functional-group tolerance and high atom economy, making it a valuable and practical method in synthetic and medicinal chemistry. Moreover, this transformation is supposed to proceed through oxidation of allylic C-H functionalization to form C-C and C-N bonds in one pot.

Red Phosphorescent Bis-Cyclometalated Iridium Complexes with Fluorine-, Phenyl-, and Fluorophenyl-Substituted 2-Arylquinoline Ligands

Red phosphorescent iridium(III) complexes based on fluorine-, phenyl-, and fluorophenyl-substituted 2-arylquinoline ligands were designed and synthesized. To investigate their electrophosphorescent properties, devices were fabricated with the following structure: indium tin oxide (ITO)/4,4′,4′′-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA)/4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB)/4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP): 8 % iridium (III) complexes/bathocuproine (BCP)/tris(8-hydroxyquinolinato)aluminum (Alq3)/8-hydroxyquinoline lithium (Liq)/Al. All devices, which use these materials showed efficient red emissions. In particular, a device exhibited a saturated red emission with a maximum luminance, external quantum efficiency, and luminous efficiency of 14200 cd m-2, 8.44 %, and 6.58 cd A-1 at 20 mA cm-2, respectively. The CIE (x, y) coordinates of this device are (0.67, 0.33) at 12.0 V. Dopant in red: Nine iridium complexes with fluorine-, phenyl-, and fluorophenyl-substituted 2-arylquinoline ligands for red phosphorescence organic light-emitting diodes were prepared. A device based on (2,4-pentanedionato)bis[2-(9,9-dimethyl-9 H-fluoren-2-yl)-5-(4-fluorophenyl)quinolinyl]iridium(III) showed an efficient deep red emission with an external quantum efficiency of 8.44 % at 20 mA cm-2.

N-heterocyclic carbene (NHC)-modulated Pd/Cu cocatalyzed three-component synthesis of 2,6-diarylquinolines

Two new NHC adducts of cyclopalladated ferrocenylpyrazine complexes 1-2 have been prepared and characterized. An efficient NHC-modulated Pd/Cu cocatalyzed three-component coupling reaction for the synthesis of 2,6-diarylquinolines from aminobenzyl alcohol