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• 62141-79-1 cyclohexylmethyl benzenesulfonate 
• 191664-04-7 4-Chloro-benzenesulfonic acid cyclohexylmethyl ester 
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• 3217-92-3 N-(cyclohexylmethyl)hydroxylamine 
• 201230-82-2 carbon monoxide 
• 110-83-8 cyclohexene 
• 53185-69-6 pimelaldehyde 

Downstream Products

• 189161-99-7 N-(cyclohexylmethylene)-4-methylaniline 

Relevant academic research and scientific papers

Heterogeneous Ru/TiO2for hydroaminomethylation of olefins: multicomponent synthesis of amines

Synthesizing aminesviathe hydroaminomethylation (HAM) reaction of olefins, a multicomponent reaction, has been regarded as one of the most attractive methods compared with the traditional methods considering the atom economy and environmental friendliness. However, the use of homogeneous catalysts, complex ligands containing diphosphine or nitrogen, and base or acid additives has severely hampered the utilization of these methods. Herein, an efficient heterogeneous Ru/TiO2-catalyzed HAM reaction of olefins is developed without any additives. Various amines, including secondary and tertiary amines, can be successfully obtained from olefins including aromatic and aliphatic olefins. Systematic studies demonstrate the lower electron density of Ruδ+and the higher number of acid sites of Ru/TiO2, leading to the high HAM reaction activity of olefins. Most importantly, nitrobenzene derivatives can also be transformed to the corresponding products over Ru/TiO2in excellent yields.

Palladium supported on magnesium hydroxyl fluoride: An effective acid catalyst for the hydrogenation of imines and N-heterocycles

Palladium catalysts supported on acidic fluorinated magnesium hydroxide Pd/MgF2-x(OH)x were prepared through precipitation or impregnation methods. Applications to the hydrogenation of various aldimines and ketimines resulted in good catalytic activities at mild temperatures using one atmosphere of hydrogen. Quinolines, pyridines and other N-heterocycles were successfully hydrogenated at higher temperature and hydrogen pressure using low palladium loadings and without the use of any acid additive. Such reactivity trend confirmed the positive effect of the Br?nsted and Lewis acid sites from the fluorinated magnesium hydroxide support resulting in the effective pre-activation of N-heterocycle substrates and therefore in the good catalytic activity of the palladium nanoparticles during the hydrogenations. As demonstrated in the hydrogenation of imines, the catalyst was recycled up to 10 times without either loss of activity or palladium leaching. This journal is

Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis

A visible-light-mediated process for dehydrogenation of amines has been described. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification. This process can be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biologically active molecules. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation.

Iron-Catalyzed Regioselective α-C-H Alkylation of N-Methylanilines: Cross-Dehydrogenative Coupling between Unactivated C(sp3)-H and C(sp3)-H Bonds via a Radical Process

The iron-catalyzed α-C-H alkylation of N-methylanilines without any directing group by cross-dehydrogenative coupling between unactivated C(sp3)-H and C(sp3)-H bonds has been established for the first time, which provides a good complement to C(sp3)-H activation reactions and expands the field of Fe-catalyzed C-H functionalizations. Many different C(sp3)-H bonds in cyclic alkanes, cyclic ethers, and toluene derivatives can be used as coupling partners. Mechanistic investigations including the radical reaction process, the main role of various reagents, and the kinetic isotope effect experiment were also described.

Metal- and Base-Free Room-Temperature Amination of Organoboronic Acids with N-Alkyl Hydroxylamines

We have found that readily available N-alkyl hydroxylamines are effective reagents for the amination of organoboronic acids in the presence of trichloroacetonitrile. This amination reaction proceeds rapidly at room temperature and in the absence of added metal or base, it tolerates a remarkable range of functional groups, and it can be used in the late-stage assembly of two complex units.

Efficient Ruthenium(II)-Catalyzed Direct Reductive Amination of Aldehydes under Mild Conditions Using Hydrosilane as the Reductant

A direct reductive amination of aldehydes with anilines is performed with a ruthenium(II)-(arene) catalyst. The [RuCl2(p-cymene)]2/Ph2SiH2 catalytic system is very efficient for the synthesis of secondary amines and tertiary amines in good yields, and is highly chemoselective, tolerating a wide range of functional groups, such as NO2, CN, CO2Me, F, Cl, Br, OMe, Me, furyl and alkyl. We also report an interesting direductive amination of 2-ethylbutanal.

Imidazolium-based ionic liquid-catalyzed hydrosilylation of imines and reductive amination of aldehydes using hydrosilane as the reductant

The first imidazolium-based ionic liquid-catalyzed hydrosilylation of imine and reductive amination of aldehydes with primary amines using a catalytic amount of 1-butyl-3-methylimidazolium tetrachloride iron [BMIm][FeCl4] and Ph2SiH2 as a reductant were performed under mild conditions. Good yields of secondary amines with high chemoselectivity and a tolerance for a wide range of functional groups were obtained.

Osmium Hydride Acetylacetonate Complexes and Their Application in Acceptorless Dehydrogenative Coupling of Alcohols and Amines and for the Dehydrogenation of Cyclic Amines

The preparation of new osmium hydride complexes, starting from OsH6(PiPr3)2 (1) and OsH2Cl2(PiPr3)2 (2), and their catalytic activity in acceptorless dehydrogenative coupling of alcohols and amines and in dehydrogenation of cyclic amines are reported. Complex 1 reacts with acetylacetone (Hacac) to give the classical trihydride OsH3(acac)(PiPr3)2 (3). The protonation of 3 with triflic acid (HOTf) produces the release of H2 and the formation of the unsaturated osmium(IV) dihydride [OsH2(acac)(PiPr3)2]OTf (4), which is also prepared by starting from 2 via the intermediate OsH2Cl(acac)(PiPr3)2 (5). Treatment of an acetylacetone solution of 5 with KOH affords Os(acac)2(PiPr3)2 (6). In the presence of 5 mol % of KOH, complexes 3-6 promote the coupling of benzyl alcohol and aniline to give N-benzylideneaniline and H2. Under the same conditions, complex 3 catalyzes a wide range of analogous couplings to afford a variety of imines, including aliphatic imines, with yields between 90 and 40% after 1-48 h. Complex 3 also catalyzes the dehydrogenation of cyclic amines. According to the amount of H2 released by each 1 g of employed substrate, the amines have been classified into three classes: poor (1,2,3,4-tetrahydroquinaldine, 2-methylindoline, and 2,6-dimethylpiperidine), moderate (1,2,3,4-tetrahydroquinoline and 6-methyl-1,2,3,4-tetrahydroquinoline), and good hydrogen donors (1,2,3,4-tetrahydroisoquinoline).

Reinvestigating Raney nickel mediated selective alkylation of amines with alcohols via hydrogen autotransfer methodology

An efficient, cost-effective use of Raney nickel (R-Ni) a widely used industrial catalyst for N-alkylation using alcohols is highlighted here. The work describes the scope and capability of R-Ni in hydrogen autotransfer reactions enabling its widespread use in the Chemical and Pharmaceutical industry. R-Ni of W4, T4, and W7 grades were prepared and evaluated for alkylation of amines. The best activity and selectivity for mono alkylation of amines were obtained using W4 R-Ni at 1:4 moles of amine to alcohol in xylene at reflux. T4 R-Ni also showed ability to form stable imines. The prepared R-Ni was also recycled and reused for N-alkylation reaction. The optimized methodology was applied for synthesis of Active Pharmaceutical ingredients Piribedil and Mepyramine. The simplicity and wide substrate scope makes this method a preferred Hydrogen Auto-transfer protocol for the alkylation of amines.

Development of a general non-noble metal catalyst for the benign amination of alcohols with amines and ammonia

The N-alkylation of amines or ammonia with alcohols is a valuable route for the synthesis of N-alkyl amines. However, as a potentially clean and economic choice for N-alkyl amine synthesis, non-noble metal catalysts with high activity and good selectivity are rarely reported. Normally, they are severely limited due to low activity and poor generality. Herein, a simple NiCuFeOx catalyst was designed and prepared for the N-alkylation of ammonia or amines with alcohol or primary amines. N-alkyl amines with various structures were successfully synthesized in moderate to excellent yields in the absence of organic ligands and bases. Typically, primary amines could be efficiently transformed into secondary amines and N-heterocyclic compounds, and secondary amines could be N-alkylated to synthesize tertiary amines. Note that primary and secondary amines could be produced through a one-pot reaction of ammonia and alcohols. In addition to excellent catalytic performance, the catalyst itself possesses outstanding superiority, that is, it is air and moisture stable. Moreover, the magnetic property of this catalyst makes it easily separable from the reaction mixture and it could be recovered and reused for several runs without obvious deactivation. Copyright