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Relevant academic research and scientific papers

PALLADIUM(II)-CATALYZED DOUBLE CARBONYLATION OF ORGANIC HALIDES IN THE PRESENCE OF AMINES: α-KETOAMIDE SYNTHESIS

Aryl, hetero-aryl, and vinylic halides react with carbon monoxide (40 atm pressure or less) and a secondary amine at 60-100 deg C in the presence of a catalytic amount of palladium compound to form α-ketoamides, in addition to simple amides as by-products.When a primary amine was used in place of a secondary one, an imine of the α-ketoamide was readily obtained.

Cu-Catalysed oxidative amidation of cinnamic acids/arylacetic acids with 2° amines: An efficient synthesis of α-ketoamides

A new and convenient copper-catalysed synthesis of α-ketoamides has been accomplished using readily available cinnamic acids/arylacetic acids and 2° amines in an open atmosphere. The reaction between cinnamic acid and amine involves the formation of enamine followed by its aerobic oxidation, whereas the reaction of arylacetic acid with amine involves amide formation followed by benzylic methylene oxidation.

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 %.

Cu(i)/{Nb6O19} catalyzed: N -acylation of arylacetic acids with amines under aerobic conditions

The method described herein is a general, efficient and green approach to synthesize α-ketoamides from arylacetic acids and amines. Employing a simple copper(i)/{Nb6O19} catalyst system, the reaction offers a facile process to give functionalized α-ketoamides from readily available arylacetic acids under aerobic conditions. The merit of this new strategy is that it expands the syntheses of α-ketoamides from stable, inexpensive and widely available acylation reagents such as arylacetic acids in one step.

Copper-catalyzed, hypervalent iodine mediated C=C bond activation of enaminones for the synthesis of α-keto amides

An unprecedented C=C bond cleavage of enaminones has been realized by means of copper catalysis in the presence of hypervalent iodine (PhI(OAc)2). The cascade transformation based on this bond cleavage leads to the synthesis of various α-keto amides. Isotope labeling experiments suggest that water has acted as a source of oxygen atoms during the generation of the new carbonyl group.

Mesoporous poly-melamine-formaldehyde stabilized palladium nanoparticle (Pd@mPMF) catalyzed mono and double carbonylation of aryl halides with amines

A new mesoporous poly-melamine-formaldehyde material supported Pd nano catalyst (mPMF-Pd0) has been synthesized and characterized by thermogravimetric analysis (TGA), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectrometry (EDS), high-resolution transmission electron microscopy (HRTEM), UV-vis diffuse reflection spectroscopy (DRS), Raman spectroscopy, X-ray photoelectron spectroscopy (XPS) and a N2 adsorption study. The mPMF-Pd0 material showed very good catalytic activity in the field of mono and double amino carbonylation of aryl bromides/iodides. Moreover, the catalyst is easily recoverable and can be reused six times without appreciable loss of catalytic activity in the above reactions. So, the highly dispersed and strongly bound palladium(0) sites in the mPMF-Pd0 could be responsible for the observed high activities. Due to strong binding with the functional groups of the polymer, no evidence of leached Pd from the catalyst during the course of reaction occurred, suggesting true heterogeneity in the catalytic process. This journal is

Aryl-palladium-NHC complex: Efficient phosphine-free catalyst precursors for the carbonylation of aryl iodides with amines or alkynes

A series of aryl-palladium-NHC compounds was prepared according to the reported methods and their catalytic activity in the carbonylation of aryl iodides to synthesize α-keto amides and alkynones was examined. These practical aryl-palladium-NHC complexes have shown highly efficient catalyzed carbonylation and Sonogashira carbonylation reactions, with high turnover number in synthesis of α-keto amides (TON = 4300) and in synthesis of alkynones (TON = 980).

Phosphine-free, efficient double carbonylation of aryl iodides with amines catalyzed by water-insoluble and water-soluble N-heterocyclic carbene-amine palladium complexes

The water-insoluble and water-soluble N-heterocyclic carbene (NHC)-amine palladium complexes, Ipr-Pd(deba)Cl and SO3-Ipr-Pd(deba)Cl, were synthesized. Both catalysts exhibit excellent activity in the phosphine-free double carbonylation of aryl iodides with amines to produce α-keto amides. Moreover, as the water-soluble catalyst exhibits significant compatibility in the aqueous phase with the activities of different Pd-NHC complexes, we conclude that the intramolecular amine ligand strongly affects the selectivity of the products in double carbonylation reaction and serves as an alternative of phosphine ligands.

NHC-Pd complex-catalyzed double carbonylation of aryl iodides with secondary amines to α-keto amides

A series of palladium-NHC compounds were prepared and their catalytic activity in the double carbonylation of aryl iodides to synthesize α-keto amides were examined. Palladium complexes bearing mixed NHC-phosphine exhibited high efficiency for the double carbonylation reaction. The effects of different solvents, base, temperature, carbon monoxide (CO), pressure, various amine and aryl iodides were investigated. Both electron-rich and electron-deficient aryl iodides afforded the corresponding substituted α-keto amides in moderate to good yields. A possible mechanism was also proposed. Copyright

Silver-catalyzed amidation of benzoylformic acids with tertiary amines via selective carbon-nitrogen bond cleavage

A novel approach towards the synthesis of α-ketoamides using tertiary amines as nitrogen group sources via C-N bond cleavage has been developed. In the presence of Ag2CO3 and K2S 2O8, α-keto acids reacted with tertiary amines to afford the corresponding α-ketoamides in good yields. The Royal Society of Chemistry 2013.