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Relevant academic research and scientific papers

Highly economical and direct amination of sp3carbon using low-cost nickel pincer catalyst

Developing more efficient routes to achieve C-N bond coupling is of great importance to industries ranging from products in pharmaceuticals and fertilizers to biomedical technologies and next-generation electroactive materials. Over the past decade, improvements in catalyst design have moved synthesis away from expensive metals to newer inexpensive C-N cross-coupling approaches via direct amine alkylation. For the first time, we report the use of an amide-based nickel pincer catalyst (1) for direct alkylation of amines via activation of sp3 C-H bonds. The reaction was accomplished using a 0.2 mol% catalyst and no additional activating agents other than the base. Upon optimization, it was determined that the ideal reaction conditions involved solvent dimethyl sulfoxide at 110 °C for 3 h. The catalyst demonstrated excellent reactivity in the formation of various imines, intramolecularly cyclized amines, and substituted amines with a turnover number (TON) as high as 183. Depending on the base used for the reaction and the starting amines, the catalyst demonstrated high selectivity towards the product formation. The exploration into the mechanism and kinetics of the reaction pathway suggested the C-H activation as the rate-limiting step, with the reaction second-order overall, holding first-order behavior towards the catalyst and toluene substrate.

Colloidal and Nanosized Catalysts in Organic Synthesis: XXIII. Reductive Amination of Carbonyl Compounds Catalyzed by Nickel Nanoparticles in a Plug-Flow Reactor

Reductive amination of aldehydes and ketones with primary and secondary amines under catalysis with nickel nanoparticles supported on zeolite X, MgO, or activated carbon in the gas phase or in the gas-liquid system in a plug-flow reactor proceeds at atmospheric pressure of hydrogen with the formation of secondary or tertiary amines in high yield.

Ruthenium-Catalyzed Amination of Secondary Alcohols Using Borrowing Hydrogen Methodology

A new ruthenium complex catalyzes the amination of primary and secondary alcohols and the regioselective mono- and sequential diamination of diols via the borrowing hydrogen pathway. Several variations on new intra- and intermolecular cyclizations of aminoalcohols, diols, and diamines lead to heterocyclic ring systems.

Reductive amination using a combination of CaH2 and noble metal

Amines were prepared by a reductive amination reaction in the presence of calcium hydride and Pt/C. The in situ formation of water seems to be the key to activate CaH2 to reduce the intermediate imine.

An efficient palladium-catalyzed N-alkylation of amines using primary and secondary alcohols

PdCl2 in the presence of dppe or Xantphos(t-Bu) as the ligand is found to be an efficient catalyst for the N-alkylation of various primary and cyclic secondary amines using primary alcohols at 90-130 C under neat conditions. Interestingly, good to excellent yields were achieved when more challenging secondary alcohols were used as alkylating agents at 130-150 C. The reaction could be easily scaled up, as demonstrated for a 10 mmol scale achieving yields up to 90% with a TON of 900.

Catalysis in flow: Au-catalysed alkylation of amines by alcohols

By using a greater reaction space afforded by a flow reactor, commercially available Au/TiO2 can be used for highly selective direct alkylation of amines by alcohols, without the need for an inert atmosphere or base. A brief survey of substrates includes the alkylation of aromatic, aliphatic and chiral amines by a number of primary and secondary alcohols, in high yield and selectivity. The synthesis of Piribedil, a drug used in the treatment of Parkinson's disease, can be achieved in a single synthetic operation without the need for column chromatography. Mechanistic aspects of the reaction were revealed through modelling of reaction profiles, and the origin of selectivity is attributed to the accessibility of high temperature. The presence of water was found to be crucial for catalyst activity.

[IrCl2Cp*(NHC)] complexes as highly versatile efficient catalysts for the cross-coupling of alcohols and amines

A comparative study on the catalytic activity of a series of [IrCl 2Cp*(NHC)] complexes in several C-O and C-N coupling processes implying hydrogen-borrowing mechanisms has been performed. The compound [IrCl2Cp*(InBu)] (Cp* = pentamethyl cyclopentadiene; InBu = 1,3-di-n-butylimidazolylidene) showed to be highly effective in the cross-coupling reactions of amines and alcohols, providing high yields in the production of unsymmetrical ethers and N-alkylated amines. A remarkable feature is that the processes were carried out in the absence of base, phosphine, or any other external additive. A comparative study with other known catalysts, such as Shvo's catalyst, is also reported.

Erbium(III) triflate: A valuable catalyst for the synthesis of aldimines, ketimines, and enaminones

Aldimines, ketimines, and enaminones can be obtained under erbium(III) inflate catalysis. The reaction mechanism is that typical of imine synthesis. The role of the catalyst is demonstrated for the synthesis of aromatic imines. In contrast to CeCl3/NaI addition to unsaturated aldehydes, which results in Michael addition, no Michael adduct was observed under erbium(III) triflate catalysis. Georg Thieme Verlag Stuttgart.

A novel ruthenium-catalyzed amination of primary and secondary alcohols

An improved method for the N-alkylation of primary amines with primary and secondary alcohols has been developed. Novel, effective catalyst systems, for example, Ru3(CO)12 combined with tri-o-tolylphosphine or n-butyl-di-1-adamantylphosphine, allow for aminations in a good yield under comparatively mild conditions.

Selective Deoxygenation of Various N-O Bonds Catalyzed by Rhodium Carbonyl Clusters in the Presence of H2O and CO and Their Heterogenization Using Amino-Substituted Polystyrenes

Catalytic deoxygenation of various N-O bonds using rhodium carbonyl compounds under a water gas shift reaction was studied.A catalyst system of Rh6(CO)16 and N,N,N',N'-tetramethyl-1,3-propanediamine was found to have high activities for the following deoxygenations: 1) conversion of nitrobenzenes to anilines, 2) aliphatic nitro compounds to nitriles, 3) oximes to nitriles, 4) hydroxylamines to amines, and 5) amine oxides to amines.The above-mentioned rhodium catalyst system was heterogenized by using amino-substituted polystyrenes.Rh6 and Rh14 carbonyl clusters of -, 2-, and 4-, were formed on the polymer surface.The characteristic features of the catalysis of the polymer-bound rhodium cluster complexes are described in relation to the corresponding homogenous ones.