37045-16-2

Upstream product

• 810695-98-8 3-benzyl-quinoline-2,4-dicarboxylic acid 
• 104-53-0 3-phenyl-propionaldehyde 
• 529-23-7 o-aminobenzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 100-52-7 benzaldehyde 
• 100-53-8 phenylmethanethiol 
• 5332-24-1 3-bromoquinoline 
• 943868-13-1 4-benzylsulfanyl-2,3,5,6-tetrafluoropyridine 
• 1589-82-8 phenylmagnesium bromide 
• 27049-45-2 benzyl 2-pyridyl ketone 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 122-97-4 3-Phenyl-1-propanol 

Downstream Products

• 37045-17-3 (S)-3-benzyl-1,2,3,4-tetrahydroquinoline 
• 101273-50-1 3-benzylquinolin-2-ol 

Relevant academic research and scientific papers

Ruthenium-Catalyzed Dehydrogenative β-Benzylation of 1,2,3,4-Tetrahydroquinolines with Aryl Aldehydes: Access to Functionalized Quinolines

A new benzylation protocol, enabling straightforward access to β-benzylated quinolines, has been demonstrated. By employing readily available [RuCl2(p-cymene)]2 as a catalyst and O2 as a sole green oxidant, various 1,2,3,4-tetrahydroquinolines were efficiently converted in combination with aryl aldehydes into desired products in a step- and atom-economic fashion together with the advantages of excellent functional group tolerance and chemoselectivity, offering an important basis for the transformation of saturated N-heterocycles into functionalized N-heteroaromatics via a dehydrogenative cross-coupling strategy. Mechanistic investigations support that the reaction undergoes a monodehydrogenation-triggered β-benzylation mode.

Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides

The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.

Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents

The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.

Synthesis of Di- and Triarylmethanes through Palladium-Catalyzed Reductive Coupling of N -Tosylhydrazones and Aryl Bromides

A palladium-catalyzed reductive coupling between N-tosylhydrazones and aryl bromides has been developed. The reaction provides an efficient method for the synthesis of diarylmethanes and triarylmethanes via the formation of C(sp2)-C(sp3) single bonds. This new methodology for the synthesis of diarylmethanes and triarylmethanes is featured by the ready availability of the starting materials, mild reaction conditions, and the tolerance of wide range of functional groups. The reaction follows a pathway including palladium carbene formation, migratory insertion, and reduction of the alkylpalladium(II) intermediate.

Synthesis of Quinolines from Allylic Alcohols via Iridium-Catalyzed Tandem Isomerization/Cyclization Combined with Potassium Hydroxide

A new tandem catalytic process has been established for the synthesis of quinolines. This process utilizes the [IrCp?Cl2]2/KOH catalyzed isomerization/cyclization of allylic alcohols with 2-aminobenzyl alcohol. Both the secondary and primary allylic alcohols were investigated in this catalytic system to afford different substituted quinoline derivatives in moderate to good yields. A mechanism study showed the reaction following a tandem process integrating isomerization of allylic alcohols and oxidative cyclization of 2-aminobenzyl alcohol.

New Iridium Catalysts for the Selective Alkylation of Amines by Alcohols under Mild Conditions and for the Synthesis of Quinolines by Acceptor-less Dehydrogenative Condensation

A novel family of iridium catalysts stabilised by P,N-ligands have been introduced. The ligands are based on imidazo[1,5-b]pyridazin-7-amines and can be synthesised with a broad variety of substitution patterns. The catalysts were synthesised quantitatively from the protonated ligands and a commercially available iridium precursor. The catalysts mediate the alkylation of amines by alcohols under mild conditions (70 °C). In addition, the synthesis of quinolines from secondary or primary alcohols and amino alcohols is reported. This sustainable synthesis proceeds through the liberation of two equivalents of water and two equivalents of dihydrogen. The investigations indicate that catalysts suitable for hydrogen autotransfer or borrowing hydrogen chemistry might also be suitable for acceptor-less dehydrogenative condensation reactions. Your H or mine? A family of catalysts that mediate the alkylation of amines by alcohols under mild conditions are introduced (see scheme; HA=hydrogen autotransfer, BH=borrowing hydrogen, ADC=acceptor-less dehydrogenative condensation). The efficient synthesis of quinolines from alcohols and amino alcohols through the liberation of two equivalents of dihydrogen is also mediated by this catalyst family.

Palladium-catalyzed synthesis of heterocycle-containing diarylmethanes through suzuki-miyaura cross-coupling

The heterocycle-containing diarylmethane synthesis from chloromethyl(hetero)arenes with (hetero)arylboron reagents was attained using the palladium/ether-imidazolium chloride system. This coupling process tolerated a diverse range of heteroaromatic moieties with sufficient catalytic activity to achieve the efficient synthesis of various diheteroarylmethanes in good to excellent yields.

Fast and convenient base-mediated synthesis of 3-substituted quinolines

In a convenient method, 3-substituted quinolines are readily synthesized in a two-step process with initial oxazine formation and subsequent base-mediated cyclization.

Suzuki-Miyaura coupling of benzylic carbonates with heteroarylboronic acids

Cross-coupling of benzylic carbonates with heteroarylboronic acids successfully proceeded in the presence of the palladium catalyst that was generated in situ from [Pd(rf-C3Hs)CI]2 and a chelate bisphosphine DPPPent. Various heteroarylboronic acids were applicable to the catalytic cross-coupling, giving the desired benzylated heteroaromatics in high yields.

A copper(II)-catalyzed protocol for modified Friedl?nder quinoline synthesis

2-Aminobenzyl alcohol reacts with an array of ketones in dioxane at 100 °C in the presence of a catalytic amount of CuCl2 along with KOH under O2 atmosphere to afford the corresponding quinolines in good yields. 2-Aminobenzyl alcohol is also oxidatively coupled and cyclized with various aldehydes by step-by-step procedure, an initial treatment of 2-aminobenzyl alcohol in the presence of CuCl2 and KOH in dioxane under O2 atmosphere and subsequent addition of aldehyde to the mixture followed by stirring under argon atmosphere, to give 3-substituted quinolines in moderate to good yields.