1574677-06-7

Upstream product

• 64-18-6 formic acid 
• 3300-51-4 p-Trifluoromethylbenzylamine 
• 123-76-2 levulinic acid 
• 455-18-5 4-CF₃C₆H₄CN 
• 455-19-6 4-Trifluoromethylbenzaldehyde 

Relevant academic research and scientific papers

Heterogeneous Pt catalysts for reductive amination of levulinic acid to pyrrolidones

Supported platinum catalysts have been studied for the reductive amination of levulinic acid (LA) by H2 to N-alkyl-5-methyl-2-pyrrolidones under solvent-free conditions. The activity depends on the type of metal (Pt, Re, Pd, Rh, Ru, Cu, Ni), support material, and coloaded oxides of transition metals (V, Cr, Mo, W, Re). In 24 kinds of catalyst tested, Pt and MoOX (molybdenum oxide) coloaded TiO2 (Pt-MoOX/TiO2) shows the highest activity. Pt-MoOX/TiO2 is effective for reductive amination of LA with wide varieties of amines under mild conditions (3 bar of H2, 100 °C, solvent-free) to give high isolated yield of pyrrolidinones and shows higher turnover number (TON) than previously reported catalysts for reductive amination of LA with an aliphatic amine. The catalyst can be separated from the reaction mixture by filtration, and the recovered catalyst can be reused. This is the first general and reusable heterogeneous catalytic system for the reductive amination of LA. On the basis of mechanistic studies, high activity of Pt-MoOX/TiO2 can be attributed to acid-base interaction between the acid sites of Pt-MoOX/TiO2 and carboxyl groups in LA and an intermediate.

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.

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.

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

NHC-based coordination polymers as solid molecular catalysts for reductive amination of biomass levulinic acid

A class of robust solid molecular NHC-based catalysts were readily fabricated via self-assembly from a p-phenylene-bridged bis-benzimidazolium salt with selected metal precursors. Among them, the NHC-Ru polymer demonstrated high catalytic activity and excellent stability as a solid molecular catalyst for the solvent-free reductive amination of biomass levulinic acid with inexpensive ammonium formate, furnishing a challenging unprotected 5-methyl-2-pyrrolidone quantitatively at a 0.15 mol% catalyst loading. The solid catalyst was readily recovered and reused for 37 runs without obvious loss of activity. Remarkably, a TON value up to 6.7 × 104 was achieved in a molar-scale reaction with a catalyst loading at 0.001 mol%. Inspired by the results of a preliminary mechanistic study, notably, one-pot tandem reductive reactions of LA with aldehydes or ketones were successfully developed, affording a variety of structurally intriguing and functional N-substituted 5-methyl-2-pyrrolidones in high chemo-selectivity with good to excellent yields.

Selective and Efficient Iridium Catalyst for the Reductive Amination of Levulinic Acid into Pyrrolidones

The catalytic reductive amination of levulinic acid (LA) into pyrrolidones with an iridium catalyst using H2 as hydrogen source is reported. The chemoselective iridium catalyst displayed high efficiency for the synthesis of a variety of N-substituted 5-methyl-2-pyrrolidones and N-arylisoindolinones. N-Substituted 5-methyl-2-pyrrolidone was also evaluated as a biosourced substitute solvent to NMP (N-methylpyrrolidone) in the catalytic arylation of 2-phenylpyridine.

Synthesis of pyrrolidones and quinolines from the known biomass feedstock levulinic acid and amines

The catalytic conversion of biomass-derived compounds into value-added products such as food additives, agrochemical components, and pharmaceutical formulations, is a promising and cost effective synthetic strategy. Here, we describe the synthesis of a variety of N-(alkyl, aryl)-5-methyl-2-pyrrolidones through the reductive amination of levulinic acid using formic acid as the hydrogen source. This system is catalyzed by 3.8 nm ruthenium nanoparticles that were prepared by thermal decomposition of [Ru3(CO)12] in solvent-free conditions. When the reactions were carried out without the catalyst, the pyrrolidones were obtained with low yield and poor selectivity. In addition, the reaction between levulinic acid and 2-ethynylaniline produced 2-(2,4-dimethylquinolin-3-yl) acetic acid (8) in mild and metal-free conditions with good yield. Furthermore, the synthesis of substituted quinolines was achieved through a condensation reaction between levulinic acid and different 2-alkynylanilines promoted by p-toluenesulfonic acid, this method is highlighted as a novel procedure for the preparation of quinolines.

Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid

Levulinic acid (LA) is transformed into pyrrolidinones by formic acid in DMSO without a catalyst. Mechanistic studies suggest the involvement of an iminium intermediate and a rate-limiting hydride transfer step.