62582-99-4

Upstream product

• 62-53-3 aniline 
• 2043-61-0 cyclohexanecarbaldehyde 
• 622-37-7 Phenyl azide 
• 1312150-38-1 dimethyl 2-(cyclohexylmethylene)-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylate 
• 98-95-3 nitrobenzene 
• 100-49-2 cyclohexylmethyl alcohol 

Downstream Products

• 1159386-68-1 N-(1-cyclohexyl-2-methylenebut-3-en-1-yl)phenylamine 
• 1231728-69-0 N-(1-cyclohexyl-3,3,3,2,2-pentafluoropropyl)aniline 
• 1312150-38-1 dimethyl 2-(cyclohexylmethylene)-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylate 
• 1613-43-0 2-cyclohexylquinoline 
• 143140-93-6 1-cyclohexyl-2-methylene-but-3-en-1-ol 

Relevant academic research and scientific papers

Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation

An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

Efficient Imine Formation by Oxidative Coupling at Low Temperature Catalyzed by High-Surface-Area Mesoporous CeO2 with Exceptional Redox Property

High-surface-area mesoporous CeO2 (hsmCeO2) was prepared by a facile organic-template-induced homogeneous precipitation process and showed excellent catalytic activity in imine synthesis in the absence of base from primary alcohols and amines in air atmosphere at low temperature. For comparison, ordinary CeO2 and hsmCeO2 after different thermal treatments were also investigated. XRD, N2 physisorption, UV-Raman, H2 temperature-programmed reduction, O2 temperature-programmed desorption, EPR spectroscopy, and X-ray photoelectron spectroscopy were used to unravel the structural and redox properties. The hsmCeO2 calcined at 400 °C shows the highest specific surface area (158 m2 g?1), the highest fraction of surface coordinatively unsaturated Ce3+ ions (18.2 %), and the highest concentration of reactive oxygen vacancies (2.4×1015 spins g?1). In the model reaction of oxidative coupling of benzyl alcohol and aniline, such an exceptional redox property of the hsmCeO2 catalyst can boost benzylideneaniline formation (2.75 and 5.55 mmol (Formula presented.) h?1 based on >99 % yield at 60 and 80 °C, respectively) in air with no base additives. It can also work effectively at a temperature of 30 °C and in gram-scale synthesis. These are among the best results for all benchmark ceria catalysts in the literature. Moreover, the hsmCeO2 catalyst shows a wide scope towards primary alcohols and amines with good to excellent yield of imines. The influence of reaction parameters, the reusability of the catalyst, and the reaction mechanism were investigated.

Efficient imine synthesisviaoxidative coupling of alcohols with amines in an air atmosphere using a mesoporous manganese-zirconium solid solution catalyst

Direct oxidative coupling of alcohols with amines using a non-precious metal oxide catalyst under mild conditions is highly desirable for imine synthesis. In this work, a mesoporous Mn1ZrxOysolid solution catalyst prepared by a co-precipitation method showed excellent catalytic performance in imine synthesis from primary alcohols and amines without base additives in an air atmosphere. XRD, N2physisorption, H2-TPR, O2-TPD, EPR and XPS were comprehensively used to unravel its structural, redox and amphoteric properties that closely depended on the interaction between MnOyand ZrO2with a variable Zr ratio. The Mn1Zr0.5Oycatalyst presented the highest fractions of Mn3+ions and reactive oxygen species on the surface, and the highest concentrations of acidic-basic sites, which were disclosed to play important roles in activating alcohols and molecular O2in the rate-determining step. In the model reaction of oxidative coupling of benzyl alcohol with aniline, such enhanced features of the Mn1Zr0.5Oycatalyst can promote the intrinsic catalytic activity (iTOF of 1.87 h?1) and boost benzylideneaniline formation (5.56 mmol gcat.?1h?1) based on a >99% yield at 80 °C respectively at a fast response. It can also work effectively at a room temperature of 30 °C, as well as for the gram-grade synthesis. This is one of the best results among all the MnOy-based catalysts in the literature. Moreover, this catalyst showed good stability and a wide substrate scope with good to excellent yields of imines.

Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ

A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.

Catalyst- And solvent-free efficient access to: N -alkylated amines via reductive amination using HBpin

A sustainable approach which works under catalyst- and solvent-free conditions for the synthesis of structurally diverse secondary amines has been uncovered. This one-pot protocol works efficiently at room temperature and is compatible with a wide range of sterically and electronically diverse aldehydes and primary amines. Notably, this simple process offers scalability, excellent functional group tolerance, chemoselectivity, and is also effective at the synthesis of biologically relevant molecules. This journal is

Efficient imine synthesis from oxidative coupling of alcohols and amines under air atmosphere catalysed by Zn-doped Al2O3 supported Au nanoparticles

Direct oxidative coupling of alcohols and amines is regarded as an effective and green approach for imine synthesis under mild conditions. In this work, Zn-doped γ-Al2O3 supported Au nanoparticles was demonstrated as highly active and selective heterogeneous catalyst for a series of imine productions with good to excellent yields, from alcohols and amines via direct oxidative coupling under air atmosphere without extra base additives. Various physicochemical techniques, including ICP-MS, XRD, N2 physisorption, TEM, XPS and CO2-/NH3-TPD, were used to study the properties of the catalysts. Well-dispersed Au0 nanoparticles with a mean size of ca. 2.9 nm were found highly effective in activating alcohols in the presence of reactive amines. The amount of Zn2+ dopant and the calcination temperature of support during catalyst preparation showed crucial impact on tuning the intrinsic activity for oxidation of benzyl alcohol to benzaldehyde (i.e., the rate-determining step for the model reaction), which was disclosed to be related with the active surface oxygen species and the acidic-basic property of support. The 0.4% Au/Zn0.02Al2O3 catalyst calcined at 400 °C exhibited the highest TOF (39.1 h?1) at 60 °C based on a >99% yield to benzylideneaniline among all the ever-reported Au-based catalysts. Moreover, this catalyst could afford 98% yield to benzylideneaniline at only 30 °C and work effectively for the gram-scale synthesis. It also showed considerable stability after five consecutive recycling.

One-pot synthesis of Pd-promoted Ce-Ni mixed oxides as efficient catalysts for imine production from the direct: N -alkylation of amine with alcohol

Ce-Ni mixed oxides with different Ni/Ce molar ratios, promoted by a rather low amount of Pd (0.2 wt%), were prepared by a simple one-pot precipitation method. The thus-synthesized CeNiXOY and Pd-CeNiXOY catalysts were applied respectively to the direct N-alkylation of amine and alcohol via oxidative coupling, under O2 in the absence of basic additives. The CeNiXOY catalyst could provide a >99% yield of imine in the model alkylation reaction of aniline with benzyl alcohol at 100 °C. The Pd-promoted Pd-CeNiXOY catalyst surprisingly showed an enhanced imine yield (>99%) at a mild temperature of 60 °C. This catalyst exhibited good reusability, and moreover, demonstrated high performance towards imine synthesis from various amines with alcohols. The presence of Pd species and the Ni/Ce molar ratio showed a synergistic impact on the conversion of aniline, as well as on the product selectivity, which was believed to be related to the improvement on the intrinsic activity of the oxidation of benzyl alcohol to benzaldehyde. Various physicochemical techniques, including ICP-MS, XRD, N2 adsorption-desorption, UV-Raman, H2-TPR, TEM, EPMA and XPS, were employed to study mainly the composition, structure and redox properties of the catalysts. The proportion of Ce3+ species and oxygen vacancies, which can be manipulated by the Ce-Ni redox system and the interaction between Ce and Ni, was crucial to the selective activation of alcohols in the presence of reactive amines. The activation of alcohol on the highly reactive Pd0 species was the other crucial factor.

Formic acid catalyzed one-pot synthesis of α-aminophosphonates: an efficient, inexpensive and environmental friendly organocatalyst

Abstract: Aqueous formic acid is used for the synthesis of α-aminophosphonates through Kabachnik–Fields reaction applying aromatic amine, phosphite, and carbonyl compounds. Using formic acid as an efficient and low-cost organocatalyst provides environmental friendly, high yields, low reaction time and mild reaction condition. The isolated products were analyzed by IR, NMR, and mass techniques. Graphical abstract: [Figure not available: see fulltext.].

Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone

The cross-dehydrogenative coupling strategy for metal-free phosphonation and cyanation of secondary N-alkyl anilines has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to imine formation, then to respective α-aminophosphonates and α-aminonitriles was proposed.