190433-55-7

Upstream product

• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 100-46-9 benzylamine 
• 887642-32-2 N-benzyl-2-hydroxy-2-(4-methoxyphenyl)acetamide 
• 32766-61-3 4-methoxyphenylglyoxylate methyl ester 
• 3672-47-7 3-oxo-3-(4'-methoxyphenyl)propanenitrile 
• 1609959-04-7 2-(4-methoxyphenyl)-2-oxo-N-phenyl-N-tosylacetamide 
• 244264-57-1 2-(4-methoxyphenyl)-N-methyl-2-oxoacetamide 
• 117177-66-9 2-(4-methoxyphenyl)-2-oxoacetyl chloride 
• 7099-91-4 p-methoxybenzoylformic acid 
• 20714-90-3 4-Methoxymandelic acid 
• 40140-16-7 ethyl (p-methoxyphenyl)oxoacetate 

Downstream Products

• 887642-52-6 (R)-N-benzyl-2-hydroxy-2-(4-methoxyphenyl)acetamide 

Relevant academic research and scientific papers

Rapid formation of amides via carbonylative coupling reactions using a microfluidic device

Carbonylative cross-coupling reactions of arylhalides to form secondary amides were rapidly carried out on a glass-fabricated microchip - the first time a microstructured device has been used to perform a gas-liquid carbonylation reaction. The Royal Society of Chemistry 2006.

Remarkable ligand effect on the palladium-catalyzed double carbonylation of aryl iodides

The use of t-Bu3P as a ligand dramatically improved the generality of the double carbonylation of aryl iodides, and Mo(CO)6 was also found to be effective as a CO source in the system. The Royal Society of Chemistry 2006.

Diversification of α-ketoamides: Via transamidation reactions with alkyl and benzyl amines at room temperature

A wide range of N-tosyl α-ketoamides underwent transamidation with various alkyl amines in the absence of a catalyst, base, or additive. On the other hand, transamidation in N-Boc α-ketoamides was achieved in the presence of Cs2CO3. The reactions proceede

Synthesis of α-Ketoamides from β-Ketonitriles and Primary Amines: A Catalyst-Free Oxidative Decyanation–Amidation Reaction

AN oxidative decyanation–amidation of β-ketonitriles and primary amines readily occurs using hydrogen peroxide sodium carbonate adduct (Na2CO3·1.5H2O2), K2CO3, and 1,4-dioxane. This reactio

Enantioselective Iridium-Catalyzed Hydrogenation of α-Keto Amides to α-Hydroxy Amides

A highly enantioselective iridium-catalyzed hydrogenation of α-keto amides to form α-hydroxy amides has been achieved with excellent results (up to >99% conversion and up to >99% ee, TON up to 100?000). As an example, this protocol was applied to the synthesis of (S)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol, the enantiomer of norepinephrine, which is widely used as an injectable drug for the treatment of critically low blood pressure. Density functional theory (DFT) calculations were also carried out to reveal the reaction mechanism.

In situ generated Pd(0) nanoparticles stabilized by bis(aryl)acenaphthenequinone diimines as catalysts for aminocarbonylation reactions in water

Aminocarbonylation of aryl iodides with aromatic and aliphatic amines, leading to formation of the corresponding amides, was efficiently carried out in water under 1?atm of CO using palladium nanoparticles (Pd NPs) formed in situ from [PdCl2(Ar2-BIAN)] complexes. The role of Ar2-BIAN ligands in the stabilization of Pd NPs was evidenced. The nature of the catalytically active species was confirmed by poisoning experiments, which highlighted that the catalyst is actually in the form of Pd NPs rather than soluble palladium complexes. In the aminocarbonylation of iodobenzene with substituted anilines good yields of amides were obtained, although the activity was depleted by the presence of substituents in the ortho positions of the aniline. On the other hand, in the reaction with aliphatic amines α-ketoamides were formed in addition to the amides. The selectivity towards α-ketoamides was increased by increasing the CO pressure to 10?atm, at equimolar amounts of PhI and amine. Pd NPs were successfully recovered after the catalytic reaction and recycled in five subsequent runs with only a marginal loss of activity after the fourth cycle.

Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330

Biocatalytic reduction of primary and secondary α-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-α-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-α-hydroxy amides.

Simplified procedure for TEMPO-catalyzed oxidation: Selective oxidation of alcohols, α-hydroxy esters, and amides using TEMPO and calcium hypochlorite

A wide range of primary and secondary multifunctional alcohols, α-hydroxyamides, and α-hydroxyesters were oxidized to their corresponding aldehydes, ketones, α-ketoamides, and α-ketoesters under mild reaction conditions using 2,2,6,6-tetramethylpiperidine-1-oxyl as a catalyst with calcium hypochlorite as an oxidant [TEMPO-Ca(OCl)2]. This simplified method does not require any transition metals, acids, or bases and demonstrates controlled and selective oxidation of structurally diverse alcohols, affording moderate to excellent yields at room temperature.

Asymmetric hydrogenation of α-keto acid derivatives by rhodium-{amidophosphine-phosphinite} catalysts

The enantioselective hydrogenation of several α-keto esters (3a-f, 5a-j), α-keto amides (7a-e) and isatine derivatives (9a-d) with a set of four representative neutral homogeneous rhodium-amidophosphine-phosphinite catalysts has been investigated. Trifluoroacetate-Rh-AMPP catalytic precursors promoted the rapid, efficient synthesis of aliphatic α-hydroxy esters 4a-f in moderate to high enantioselectivities (66-95% eel, in contrast to most aromatic α-hydroxy esters 6a-j (8-81% eel. Best enantioselectivities for α-hydroxy amides 8a-e (85-95% eel and dioxindoIes 10a-d (80-94% eel were obtained with chloro-Rh-AMPP precursors. It is proposed that, contrary to α-keto amides, α-keto esters do not chelate onto the rhodium center and that, in such circumstances, the asymmetric induction is mainly controlled by the steric hindrance around the C=O function.