634606-85-2

Upstream product

• 98-86-2 acetophenone 
• 552-89-6 2-nitro-benzaldehyde 
• 14762-47-1 2-diazo-3-oxo-3-phenylpropanal 
• 15397-33-8 3-Oxo-3-phenylpropanal 
• 13735-81-4 1-styrenyloxytrimethylsilane 

Downstream Products

• 612-96-4 2-Phenylquinoline 
• 5659-33-6 2-phenylquinoline 1-oxide 
• 53744-31-3 2-nitrochalcone 

Relevant academic research and scientific papers

Deciphering a Reaction Network for the Switchable Production of Tetrahydroquinoline or Quinoline with MOF-Supported Pd Tandem Catalysts

A mechanistic study of heterogeneous tandem catalytic systems is crucial for understanding and improving catalyst activity and selectivity but remains challenging. Here, we demonstrate that a thorough mechanistic study of a multistep reaction can guide us to the controllable selective synthesis of phenyltetrahydroquinoline or phenylquinoline with easily accessible precursors. The one-pot production can be achieved, catalyzed by a well-defined, bifunctional metal-organic framework-supported Pd nanoparticles, with only water as the side product. Our mechanistic study identifies six transient intermediates and ten transformation steps from the operando magic angle spinning nuclear magnetic resonance study under 27.6 bar H2. In particular, reactive intermediate 2-phenyl-3,4-dihydroquinoline cannot be observed with conventional chromatographic techniques but is found to reach the maximal concentration of 0.11 mol L-1 under the operando condition. The most probable reaction network is further deduced based on the kinetic information of reaction species, obtained from both operando and ex situ reaction studies. This deep understanding of the complex reaction network enables the kinetic control of the conversions of key intermediate, 2-phenyl-3,4-dihydroquinoline, with the addition of a homogeneous co-catalyst, allowing the selective production of tetrahydroquinoline or quinoline on demand. The demonstrated methods in this work open up new avenues toward efficient modulation of reactions with a complex network to achieve desired selectivities.

Strong Lewis acid air-stable cationic titanocene perfluoroalkyl(aryl) sulfonate complexes as highly efficient and recyclable catalysts for C-C bond forming reactions

A series of strong Lewis acid air-stable titanocene perfluoroalkyl(aryl) sulfonate complexes Cp2Ti(OH2)2(OSO 2X)2·THF (X = C8F17, 1·THF; X = C4F9, 2·H2O· THF; X = C6F5, 3) were successfully synthesized by the treatment of Cp2TiCl2 with C8F 17SO3Ag, C4F9SO3Ag and C6F5SO3Ag, respectively. In contrast to well-known titanocene bis(triflate), these complexes showed no change in open air over three months. TG-DSC analysis showed that 1·THF, 2·H 2O·THF and 3 were thermally stable at 230 °C, 220°C and 280°C, respectively. Conductivity measurements showed that these complexes underwent ionic dissociation in CH3CN solution. X-ray analysis results confirmed that 2·H2O·THF and 3 were cationic. ESR spectra showed that the Lewis acidity of 1·THF (1.06 eV) was higher than that of Sc3+ (1.00 eV) and Y3+ (0.85 eV). UV/Vis spectra showed a significant red shift due to the strong complex formation between 10-methylacridone and 2·H2O·THF. Fluorescence spectra showed that the Lewis acidity of 2 (λem = 477 nm) was higher than that of Sc3+ (λem = 474 nm). These complexes showed high catalytic ability in various carbon-carbon bond forming reactions. Moreover, they show good reusability. Compared with 1·THF, 2·H2O·THF and 3 exhibit higher solubility and better catalytic activity, and will find broad applications in organic synthesis. This journal is the Partner Organisations 2014.

Alkaline earth metal-based metal-organic framework: Hydrothermal synthesis, X-ray structure and heterogeneously catalyzed Claisen-Schmidt reaction

Two alkaline earth metal-based carboxylate systems, [Mg(HL)(H 2O)2]n (1) and [Ca(H2L) 2]n (2) (H3L = chelidamic acid) have been hydrothermally synthesized, and characterized by single-crystal X-ray diffraction, IR, elemental analysis, and thermo-gravimetric analysis. Compound 1 has a 2D structure incorporating two water molecules. The dehydrated species, 1a, generated from 1 by removal of the coordinated water, has been characterized by thermo-gravimetric analysis, IR, elemental analysis and variable temperature powder X-ray diffraction. Both 1 and its dehydrated species 1a catalyze the Claisen-Schmidt reaction under heterogeneous conditions, but 1a is a more effective catalyst under environmentally friendly conditions. The catalyst can readily be recovered and reused in successive cycles without detectable loss of activity. Compound 2 has a 3D structure and is thermally stable up to 540 °C, but is inactive catalytically. This journal is the Partner Organisations 2014.

Synthesis and structures of air-stable binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate and their catalytic application in C-C bond-forming reactions

The two air-stable m2-hydroxy-bridged binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate complexes were successfully synthesized. The high catalytic activity and recyclability of these complexes were exemplified for various carbon-carbon bond formation reactions. Compared with our previously reported hafnocene perfluorooctanesulfonate, these complexes show stronger Lewis acidity and better catalytic activity, and should find broad applications in organic synthesis.

Chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal with aldehydes and ketones

The chemoselectivity in the reaction of 2-diazo-3-oxo-3-phenylpropanal (1) with aldehydes and ketones in the presence of Et3N was investigated. The results indicate that 1 reacts with aromatic aldehydes with weak electron-donating substituents and cyclic ketones under formation of 6-phenyl-4H-1,3-dioxin-4-one derivatives. However, it reacts with aromatic aldehydes with electron-withdrawing substituents to yield 1,3-diaryl-3-hydroxypropan-1-ones, accompanied by chalcone derivatives in some cases. It did not react with linear ketones, aliphatic aldehydes, and aromatic aldehydes with strong electron-donating substituents. A mechanism for the formation of 1,3-diaryl-3-hydroxypropan-1-ones and chalcone derivatives is proposed. We also tried to react 1 with other unsaturated compounds, including various olefins and nitriles, and cumulated unsaturated compounds, such as N,N′-dialkylcarbodiimines, phenyl isocyanate, isothiocyanate, and CS2. Only with N,N′-dialkylcarbodiimines, the expected cycloaddition took place. Copyright

A magnesium-based multifunctional metal-organic framework: Synthesis, thermally induced structural variation, selective gas adsorption, photoluminescence and heterogeneous catalytic study

Three magnesium based carboxylate framework systems were prepared through a temperature-dependent synthesis. The compounds were synthesized by a hydrothermal method and characterized by single crystal X-ray diffraction analysis. A stepwise increase in the

A novel simple bifunctional catalyst for the direct aldol reaction

Direct aldol reactions of aldehydes and ketones can proceed smoothly in the presence of a catalytic amount of naphthol/sodium naphtholate (5 mol%) to afford the corresponding products with yields up to 98%. Such a bifunctional catalyst is more moderate than strong acid or base employed in direct aldol reactions.

Development of N,N-bis(perfluoroalkanesulfonyl)squaramides as new strong Br?nsted acids and their application to organic reactions

New strong Br?nsted acids derived from a squaric acid scaffold bearing different perfluoroalkanesulfonyl groups have been developed and applied to several organic reactions. These squaramides are bench-stable and exhibit much higher reactivities in several organic reactions than squaric acid itself. N,N-Bis(trifluoromethanesulfonyl)squaramide 2a was applied to the Mukaiyama aldol reaction and Mukaiyama Michael reaction. Mechanistic studies revealed that the Br?nsted acid might be the predominant catalyst through direct protonation of carbonyl compound by the acid itself rather than the silylated Br?nsted acid. The utility of this acid 2a was further extended to Hosomi-Sakurai allylation of aldehydes and a carbonyl-ene reaction. Furthermore, other squaramides 2b and c bearing longer perfluoroalkyl chains have been developed, which are also bench-stable and displayed similar reactivities with squaramide 2a in several organic reactions.

Chemoselective synthesis of quinoline N-oxides from 3-(2-nitrophenyl)-3- hydroxypropanones

The reaction of 3-(2-nitrophenyl)-3-hydroxypropanones with Zn/NH 4Cl gave the corresponding quinoline N-oxides in 80-90% yields. The reaction initiated the reduction of nitro group to afford the corresponding hydroxylamine, which intramolecularly condensed and followed by dehydration to give quinoline N-oxide. Although treatment of 2-nitrochalcone with Zn/NH 4Cl in EtOH/H2O resulted in the formation of quinoline N-oxide in low yield, the reaction of 2-nitrochalcone with Sn/NH4Cl in refluxing EtOH/H2O afforded quinoline N-oxide in 80% yield.

Environmentally Friendly and Efficient Process for the Preparation of β-Hydroxyl Ketones

An environmentally benign and efficient process for the preparation of β-hydroxyl ketones was developed by the practical cross-aldol reactions of 2-acetylpyridine, acetophenone, and cyclohexanone with 4-nitro-, 3-nitro-, and 2-nitrobenzaldehydes in water