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Relevant academic research and scientific papers

Preparation method of alpha-carbonyl amide compound

The invention discloses a preparation method of an alpha-carbonyl amide compound. The method comprises the following steps: under the action of a catalyst, taking oxygen as an oxidant, and carrying out oxidative amidation reaction on an alpha-diazoketone compound shown in a chemical formula 2 and a cyclic secondary amine compound shown in a chemical formula 3 in an organic solvent to obtain the alpha-carbonyl amide compound shown in a chemical formula 1, wherein the formulas 1, 2 and 3 are also shown in the speification. According to the preparation method disclosed by the invention, the alpha-carbonyl amide compound is obtained by taking oxygen as the oxidizing agent and catalyzing alpha-diazoketone and cyclic secondary amine to be subjected to oxidative amidation reaction through cuprous iodide, the reaction condition is mild, the reaction time is short, and the byproduct of the reaction is only nitrogen, so that the method is an effective way for green and efficient preparation of the alpha-carbonyl amide compound.

Cu(OAc)2 and acids promoted the oxidative cleavage of α-aminocarbonyl compounds with amines: efficient and selective synthesis of 2-t-amino-2-imino-carbonyl and 2-amino-2-oxocarbonyl

A novel and efficient method for the synthesis of 2-t-amino-2-imino-carbonyl (C) and 2-amino-2-oxocarbonyl (D) compounds has been discovered through a copper-promoted oxidating amidation reactions between α-amino -carbonyl compounds and amines. Promoted by the crucial copper species, perfect selectivity and good to excellent yields could be achieved. This transformation is achieved through C[sbnd]N bond oxidative cleavage and formation a novel C[sbnd]N bond. This reaction system has a broad reaction scope, providing a facile pathway for the α-functionalization of α-amino ketones.

Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides

A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.

Double carbonylation of iodoarenes in the presence of a pyridinium SILP-Pd catalyst

The efficiency of a palladium catalyst, immobilised on a supported ionic liquid phase (SILP) with adsorbed 1-butyl-4-methylpyridinium chloride, was investigated in aminocarbonylation reactions. Double carbonylation was found to be the main reaction using different iodoarenes and aliphatic amines as substrates. Application of aniline derivatives as nucleophiles led to the exclusive formation of substituted benzamides. The stabilisation effect of the adsorbed pyridinium ionic liquid was compared to that of imidazolium and phosphonium derivatives. It was proved that the pyridinium SILP-palladium catalyst could be reused in at least 10 cycles. Recyclability was tested in five successive runs for all of the substrates.

POP-Pd(ii) catalyzed easy and safe: In situ carbonylation towards the synthesis of α-ketoamides from secondary cyclic amines utilizing CHCl3 as a carbon monoxide surrogate

A novel complex catalyst, POP-palladium(ii), has been synthesized. The developed catalyst has been characterized by XRD, EDX, scanning electron microscopy (FE-SEM), HR-TEM, FTIR spectroscopy, UV-vis spectroscopy, TGA and BET isotherm analysis. The reactiv

Polymer supported triazine based palladium complex catalyzed double carbonylation reaction of halo aryl compounds for the synthesis of α-ketoamides

Novel polystyrene incorporated Palladium (II) catalyst was developed and well characterized. The efficiency of the supported Pd(II) catalytic material was checked for double carbonylation reaction of 2° amines and aryl iodides to their corresponding α-ketoamides under high pressure reaction conditions. The reaction was carried out in 60 psi carbon monoxide pressure. An extensive variety of aryl iodides in combination with 2° amines in presence of carbon monoxide can produce the respective α-ketoamides with superb chemoselectivity. Effect of solvents, bases, time and amount of catalyst for the production of α-ketoamides were reported. This supported Pd(II)complex was highly catalytically active and recyclable. The developed catalytic material was regenerated by filtration. It could be recycled further six times with no such profound loss in its activity.

Copper-catalyzed oxidative synthesis of 2-oxo-acetamidines from one-pot three-component reaction of aryl methyl ketones, secondary amines and anilines

Some novel 2-oxo-acetamidines were synthesized via one-pot three-component reaction of acetophenones, secondary amines and anilines in presence of CuI as catalyst. The reaction involved in a oxidation process of C (sp3)–H bonds of acetophenones

Double carbonylation of iodoarenes in the presence of reusable palladium catalysts immobilised on supported phosphonium ionic liquid phases

The first heterogeneous carbonylation reaction carried out with palladium catalysts immobilised on phosphonium ion modified silica supports is reported. The supported ionic liquid phases were characterised by solid state NMR and FT-IR measurements. The presence of the phosphonium ions on the surface made it possible to carry out double carbonylation in apolar toluene efficiently that resulted in reduced metal leaching. The introduction of dicationic moieties on the solid support has been proved to lead to a further increase in catalyst stability. The catalysts were proved to produce α-ketoamide products with excellent selectivity in the carbonylation of iodoarenes with aliphatic amines while monocarbonylation was the only reaction observed with aniline derivatives. The catalysts could be recycled and used in at least 10 subsequent runs under optimised conditions.

UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution

Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.

Mono- and double carbonylation of aryl iodides with amine nucleophiles in the presence of recyclable palladium catalysts immobilised on a supported dicationic ionic liquid phase

Silica modified with organic dicationic moieties proved to be an excellent support for palladium catalysts used in the aminocarbonylation of aryl iodides. By an appropriate choice of the reaction conditions, the same catalyst could be used for selective mono- or double carbonylations leading to amide and α-ketoamide products, respectively. The best catalyst could be recycled for at least 10 consecutive runs with a loss of palladium below the detection limit. By the application of the new support, efficient catalyst recycling could be achieved under mild reaction conditions (under low pressure and in a short reaction time). Palladium-leaching data support a mechanism with dissolution - re-precipitation of the active palladium species.