61831-63-8

Upstream product

• 110-62-3 pentanal 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 5344-90-1 2-Aminobenzyl alcohol 
• 1009-14-9 phenyl butyl ketone 
• 27527-32-8 2-Anilino-hexansaeure 
• 3684-12-6 2-phenyl-2-(phenylamino)acetic acid 
• 583-03-9 1-Phenyl-1-pentanol 
• 61752-65-6 1-phenylpent-2-en-1-one 
• 4403-69-4 2-amino-1-benzylamine 

Relevant academic research and scientific papers

Iridium-Catalyzed Transfer Hydrogenation for Construction of Quinolines from 2-Aminobenzyl Alcohols with Enones in Water

Herein, we describe a method for the synthesis of functionalized quinolines from 2-aminobenzyl alcohols with -nsaturatedketones.This method exhibits tolerance to various functional groups and high efficiency, is environmentally benign, and can be performed on a gram scale. Control experiments suggest that this transformation is accomplished by iridium complex catalyzed transfer hydrogenation, which is then followed by Friedl nder cyclization. The results display that alkali is essential for the high selectivities of this catalytic system.

Phosphine Ligand-Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions

A series of phosphine-free Ru(III)/Ru(II) complexes of NH functionalized N?N?N pincer ligands exhibit excellent activity for acceptorless dehydrogenative coupling (ADC) of secondary alcohols with 2-aminobenzyl or γ-amino alcohols to quinolines and pyridines. Ru(III) complexes [LRuCl3] (L=6-(3-R1,5-R2-1H-pyrazol-1-yl)-N-(pyridin-2-yl)pyridin-2-amine; 1 a: R1=R2=H (L1); 1 b: R1=R2=Me (L2); 1 c: R1=H, R2=CF3 (L3); 1 d: R1=H, R2=Ph (L4); 1bMe: L=6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-methyl-N-(pyridin-2-yl)pyridin-2-amine (L2Me)) were obtained by refluxing RuCl3 ? xH2O with the corresponding ligand in EtOH. Five Ru(II) complexes [LRu(DMSO-κS)Cl2] (2 a: L=L1; 2 b: L=L2; 2 c: L=L3; 2 d: L=L4; 2bMe: L=L2Me) were formed by reducing the corresponding Ru(III) complex in refluxing EtOH. The latter complexes could also be prepared directly by refluxing Ru(DMSO)4Cl2 with the corresponding ligand in EtOH. These Ru(III) and Ru(II) complexes, especially 1 b/2 b, exhibited high catalytic efficiency and broad functional group tolerance in ADC reactions of secondary alcohols with 2-aminobenzyl or γ-amino alcohols to quinolines and pyridines. A detail mechanistic study indicated the Ru(III) complex was reduced into the Ru(II) species, which is the active catalytic center for ADC via a Ru?H/N?H bifunctional outer-sphere mechanism. This protocol provides a reliable, atom-economical and environmentally benign procedure for C?N and C?C bond formation.

Highly Diastereo- And Enantioselective Ir-Catalyzed Hydrogenation of 2,3-Disubstituted Quinolines with Structurally Fine-Tuned Phosphine-Phosphoramidite Ligands

A highly diastereo- and enantioselective Ir-catalyzed hydrogenation of unfunctionalized 2,3-disubstituted quinolines, especially 3-alkyl-2-arylquinolines, has been realized. The success of this hydrogenation is ascribed to the use of a structurally fine-tuned chiral phosphine-phosphoramidite ligand with a (Sa)-3,3′-dimethyl H8-naphthyl moiety and (Rc)-1-phenylethylamine backbone. The hydrogenation displayed broad functional group tolerance, thus furnishing a wide range of optically active 2,3-disubstituted tetrahydroquinolines in up to 96% ee and with perfect cis-diastereoselectivity.

Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of N-Aryl α-Amino Acids

A visible-light-driven sequential photoredox catalysis to allow N-aryl α-amino acids to experience efficient cascade aerobic decarboxylative Povarov and oxidative dehydrogenation (ODH) reactions is described. With a dicyanopyrazine-derived chromophore (DP

Nickel-Catalyzed Hydrogen-Borrowing Strategy for α-Alkylation of Ketones with Alcohols: A New Route to Branched gem-Bis(alkyl) Ketones

The α-alkylation of ketones using an earth-abundant and nonprecious NiBr2/L1 system is reported. This nickel-catalyzed reaction could be performed in gram scale and successfully applied in the synthesis of donepezil (Alzheimer's drug) and functionalization of steroid hormones and fatty acid derivatives. Synthesis of N-heterocycles, methylation of ketones, and one-pot double alkylation to bis-hetero aryl ketones using two different alcohols with a single catalyst broadens the scope of the catalytic protocol. Preliminary mechanistic studies using defined Ni-H species and deuterium-labeling experiments established the participation of the borrowing-hydrogen strategy.

An efficient synthesis of quinolines via copper-catalyzed C-N cleavage

An efficient method to synthesize substituted quinolines from ketones and 2-amino benzylamines is described. Copper-catalyzed C-N cleavage of amines followed by condensation with ketones deliver quinolines in moderate to high yields. The broad scope of su

Enantioselective Metal-Free Hydrogenations of Disubstituted Quinolines

A metal-free hydrogenation of 2,4-disubstituted quinolines was realized for the first time using chiral diene derived borane catalysts to furnish the corresponding tetrahydroquinolines in 75-98% yields with 95/5-99/1 dr's and 86-98% ee's. This catalytic system was also effective for 2,3-disubstituted quinolines to give moderate to good ee's.

Lithium tert-butoxide mediated α-alkylation of ketones with primary alcohols under transition-metal-free conditions

LiOtBu was found to efficiently promote the α-alkylation reaction of ketones with primary alcohols, without the addition of any transition metal catalyst.

Different reactivities of Alkoxy- And Thiocarbene complexes of fischer-type: Formation of (N-Enamino)ethoxycarbene complexes and Quinolines, respectively

Alkoxy- and thiocarbene complexes of chromium and tungsten afford different type of products on reaction with (N-aryl)imidoyl chlorides. The (n-butyl)ethoxycarbene complex [(OC)5W=C(OEt)n-Bu] and (N-aryl)imidoyl chlorides t-BuClC=NC6H4R4 (R4 = H, OMe) undergo a rearrangement to (N-enamino)ethoxycarbene complexes, whereas quinolines are obtained from the corresponding reaction of(alkyl)thiocarbene complexes [(OC)5M=C(SEt)CH2R] (M = W, Cr; R = n-Pr,Me)with (N-aryl)imidoyl chlorides R1ClC=NC 6H2R2R3R4 (R1 = t-Bu, Ph; R2, R3 = H, HC=CH-CH=CH; R4 = H, OMe, Me) by β-cyclization.

SYNTHESIS OF SUBSTITUTED QUINOLINES VIA THE CONDENSATION OF ANILINES WITH ALIPHATIC AND AROMATIC ALDEHYDES IN THE PRESENCE OF TRANSITION METAL AND RARE-EARTH METAL CATALYSTS

Novel catalyst complexes derived from transition metal and rare-earth metal compounds have been developed for the condensation of anilines with aliphatic and aromatic aldehydes to give the corresponding 2,3-disubstituted quinolines in high yields.