18518-40-6

Upstream product

• 108-91-8 cyclohexylamine 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 98-95-3 nitrobenzene 
• 123-76-2 levulinic acid 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 73964-79-1 N-cyclohexyl 4-oxo-pentanamide 
• 766-93-8 N-cyclohexylformamide 
• 58839-90-0 N-cyclohexyl-4-pentenamide 
• 108-94-1 cyclohexanone 
• 1122-60-7 1-nitrocyclohexane 
• 64-18-6 formic acid 
• 57-48-7 D-Fructose 
• 62-53-3 aniline 

Relevant academic research and scientific papers

PCET-Enabled Olefin Hydroamidation Reactions with N-Alkyl Amides

Olefin aminations are important synthetic technologies for the construction of aliphatic C-N bonds. Here we report a catalytic protocol for olefin hydroamidation that proceeds through transient amidyl radical intermediates that are formed via proton-coupl

Transfer Hydrogenation of Levulinic Acid to γ-Valerolactone and Pyrrolidones Using a Homogeneous Nickel Catalyst

We report a well-defined homogeneous nickel-based catalyst using the complex [dippeNi(COD)] (dippe=1,2-bis(diisopropyl phosphino)ethane) as a catalytic precursor with high activity in the hydrogenation of levulinic acid (LVA) to yield γ-valerolactone (GVL) under relatively mild conditions (4 h, 120 °C); formic acid (FA) is the transfer hydrogenation agent in a dehydrogenation-hydrogenation process. Under optimized conditions, GVL was obtained with excellent yield (>99 %) and selectivity (>99 %). The Ni-catalyst was assessed in the LVA hydrogenation with a variety of primary amines using an excess of FA (4 eq) as hydrogen donor at 15 h and 170 °C to produce 2-pyrrolydones with excellent yield (>99 %) and fair to good selectivity (from 68 to 92 %).

Reductive amination of levulinic acid to N-substituted pyrrolidones over RuCl3 metal ion anchored in ionic liquid immobilized on graphene oxide

Reductive amination of biomass derived Levulinic acid (LA) for the synthesis of N-substituted pyrrolidones is one of the highly attractive routes for biomass valorization. The supported homogeneous metal precursor into the solid surface is an important context in the field of catalysis because these types of catalysts provide the heterogeneous nature and meet the needs of recyclability. Herein, we have reported a synthesis of catalyst with ruthenium ion supported on ionic liquid immobilized into graphene oxide (Ru?GOIL) and its application for reductive amination reaction. Synthesized catalyst is characterized using different analytical techniques such as FT-IR, XRD, XPS, TGA, FEG-SEM, TEM and EXAFS analysis. The prepared Ru?GOIL found to be highly effective for reductive amination of LA and under these optimized conditions various N-substituted pyrrolidones derivatives were synthesized in excellent yield (78–93%). Ru?GOIL catalyst demonstrated great catalytic performance for reductive amination reaction of LA giving good turnover frequency (TOF = 62 h?1) value in comparison with other catalysts. The Ru?GOIL catalyst was recycled for six reaction runs with slight drop-in activity after 4th cycle. Practical applicability of the developed catalyst was successfully demonstrated by direct transformation of biomass waste (rice husk and wheat straw) derived LA to N-substituted pyrrolidones.

Ambient reductive synthesis of N-heterocyclic compounds over cellulose-derived carbon supported Pt nanocatalyst under H2atmosphere

N-heterocyclic compounds are important chemicals, and their reductive synthesis using H2 under mild conditions is attractive but challenging. Herein, we report chemoselective hydrogenation of 2-nitroacylbenzenes to 2,1-benzisoxazoles under ambient conditions for the first time, wihch is achieved over cellulose-derived carbon (c-C) supported Pt nanocatalyst (Pt/c-C), and a series of 2,1-benzisoxazoles can be obtained in excellent yields. Pt/c-C also shows high performance for ambient reductive amination of levulinic acid with H2, accessing various pyrrolidones in excellent yields. The systematic studies indicated that the c-C support played multiple roles in catalysis with enhancing electron density of the Pt nanoparticles and activating reactant molecules. Especially, the O-containing groups on the c-C surface provided the c-C support with both acid and base features, thus endowing Pt/c-C with high performances. This work provides an accessible and highly efficient catalyst for reductive synthesis of N-heterocycles using H2 under ambient conditions, which may have promising applications.

One-pot synthesis of pyrrolidones from levulinic acid and amines/nitroarenes/nitriles over the Ir-PVP catalyst

The synthesis of pyrrolidones via reductive amination of levulinic acid with aniline was examined over polypyrrolidone-stabilized metal nanoparticle catalysts. Among them, Ir metal was the most effective and applicable for the reductive amination of levulinic acid with nitroarenes/nitriles. Importantly, this catalyst was used for the one-pot synthesis of the anti-inflammatory drug indoprofen from 2-formylbenzoic acid and 2-(4-nitrophenyl)propanoic acid.

Ambient Reductive Amination of Levulinic Acid to Pyrrolidones over Pt Nanocatalysts on Porous TiO2 Nanosheets

Construction of N-substituted pyrrolidones from biomass-derived levulinic acid (LA) via reductive amination is a highly attractive route for biomass valorization. However, realizing this transformation using H2 as the hydrogen source under mild conditions is still very challenging. Herein, we designed porous TiO2 nanosheets-supported Pt nanoparticles (Pt/P-TiO2) as the heterogeneous catalyst. The prepared Pt/P-TiO2 was highly efficient for reductive amination of LA to produce various N-substituted pyrrolidones (34 examples) at ambient temperature and H2 pressure. Meanwhile, Pt/P-TiO2 showed good applicability for reductive amination of levulinic esters, 4-acetylbutyric acid, 2-acetylbenzoic acid, and 2-carboxybenzaldehyde. Systematic studies indicated that the strong acidity of P-TiO2 and the lower electron density of the Pt sites as well as the porous structure resulted in the excellent activity of Pt/P-TiO2.

Formic acid as a hydrogen source for the iridium-catalyzed reductive amination of levulinic acid and 2-formylbenzoic acid

The aqueous phase catalytic reductive amination of levulinic acid (LA) into pyrrolidones and 2-formylbenzoic acid into N-arylisoindolines is reported. The catalytic reaction involves an iridium catalyst bearing an electron-rich dipyridylamine ligand and u

Iron-Catalysed Switchable Synthesis of Pyrrolidines vs Pyrrolidinones by Reductive Amination of Levulinic Acid Derivatives via Hydrosilylation

A selective production of pyrrolidines vs pyrrolidinones via hydrosilylation of levulinic acid and levulinates by switching of the iron complex catalyst is presented herein. The reactions proceeded efficiently with various anilines and alkylamines under both visible light irradiation and thermal conditions with 43 examples in isolated yields up to 93%. Noticeably, under similar conditions, cyclic amines such as piperidines and azepanes were efficiently synthesized with yields up to 92%, by reaction of anilines with 1,5- or 1,6-keto acids, respectively. Similarly, N-arylinsolidoline compounds can be prepared from 2-formylbenzoic acid in 57–93% yields. (Figure presented.).

A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen

Lactams are privileged in bioactive natural products and pharmaceutical agents and widely featured in functional materials. This study presents a novel versatile approach to the direct synthesis of lactams from oxocarboxylic acids without catalyst or external hydrogen. The method involves the in situ release of formic acid from formamides induced by water to facilitate efficient cycloamination. Water also suppresses the formation of byproducts. This unconventional pathway is elucidated by a combination of model experiments and density functional theory calculations, whereby cyclic imines (5-methyl-3,4-dihydro-2-pyrrolone and its tautomeric structures) are found to be favorable intermediates toward lactam formation, in contrast to the conventional approach encompassing cascade reductive amination and cyclization. This sustainable and simple protocol is broadly applicable for the efficient production of various N-unsubstituted and N-substituted lactams.

Reductive amination of ethyl levulinate to pyrrolidones over AuPd nanoparticles at ambient hydrogen pressure

Herein, we describe a AuPd catalyst for selective and solventless conversion of ethyl levulinate (EL) and amines to pyrrolidones under ambient pressure. The optimized Au66Pd34 nanoparticle catalyst was stable and reusable over 10 runs. AuPd catalysis was extended to reductive amination of levulinic acid and 4-acetylbutyric acid, providing a green chemistry approach under milder conditions not only to pyrrolidones, but also to piperidines, both of which are important scaffolds in designing polymers, natural products and pharmaceuticals.