447431-60-9

Upstream product

• 123-75-1 pyrrolidine 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 1532548-78-9 1-(prop-2-ene-1-sulfinyl)pyrrolidine 
• 120-94-5 1-Methylpyrrolidine 
• 166539-79-3 2,3,4,5,6-pentafluorophenyl 4-(trifluoromethyl)benzoate 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 65017-76-7 N-methyl-4-(trifluoromethyl)benzamide 
• 402-43-7 p-trifluoromethylphenyl bromide 

Downstream Products

• 1110635-83-0 (2-(1,2-diphenylvinyl)-4-trifluoromethylphenyl)pyrrolidin-1-ylmethanone 
• 447431-42-7 N-(4-methylphenyl)-4-(trifluoromethyl)benzamide 
• 1373312-52-7 C₂₆H₂₅F₃N₂O₃S 

Relevant academic research and scientific papers

Synthesis of α-Aminosilanes by 1,2-Metalate Rearrangement Deoxygenative Silylation of Aromatic Amides

An efficient nickel-catalyzed deoxygenative silylation reaction of aromatic amides with silylboranes in the presence of a Sm/SmI2system for the construction of α-aminosilanes is described. This strategy provides a direct method for synthesizing α-aminosilanes with high efficiency and good functional group compatibility and includes readily accessible starting materials and valuable products.

Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals

We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Cobalt(iii)-catalyzed C-H amidation of: N, N -dialkyl thiobenzamides by sulfur coordination

An efficient inexpensive cobalt(iii)-catalyzed intermolecular amidation of N,N-dialkyl thiobenzamides with 1,4,2-dioxazol-5-ones via C-H bond activation is described. The reaction proceeds with high functional group tolerance under external oxidant free conditions, providing a straightforward approach for the direct modification of thioamide derivatives, which are prevalent organic motifs found in vital biological and pharmaceutical molecules. This journal is

Photocatalytic aldehydes/alcohols/toluenes oxidative amidation over bifunctional Pd/MOFs: Effect of Fe-O clusters and Lewis acid sites

Heterogeneous photocatalytic organic synthesis is fascinating because of the utilization of ubiquitous solar light for chemical transformations. Here, three Fe-MOFs with different Fe-O clusters, Lewis acid sites and morphologies were synthesized through coordination structure engineering. Pd/Fe-MOFs nanocomposites were used to challenge the amide bond green synthesis with visible light. Pd/MIL-101(Fe) exhibited the best photocatalytic performance due to the easily excited Fe3-μ3-oxo clusters for light absorption, the efficient photogenerated carriers separation and migration, the large amount of Lewis acid sites based aldehydes and amines condensation promotion and the efficient O2 reduction to superoxide radicals over photogenerated electron-rich Pd NPs. Various aldehydes, alcohols and toluenes could be transformed to amide compounds with amines over Pd/MIL-101(Fe) with just oxygen or air as the green oxidant and water as the by-product. One-pot C–C cross-coupling and photo-redox C–N coupling cascade reactions could also be achieved over Pd/MIL-101(Fe). This work shed light on the efficient and sustainable amide bonds synthesis.

Visible-Light-Mediated Oxidative Amidation of Aldehydes by Using Magnetic CdS Quantum Dots as a Photocatalyst

A magnetic CdS quantum dot (Fe3O4/polydopamine (PDA)/CdS) was synthesized through a facile and convenient method from inexpensive starting materials. Characterization of the prepared catalyst was performed by means of FTIR spectrosco

Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides

Herein, we report a one-electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross-coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive-functional-group-containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron-poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods.

Ruthenium(II)-catalyzed C-H arylation of N,N-dialkyl thiobenzamides with boronic acids by sulfur coordination in 2-MeTHF

We report ruthenium(II)-catalyzed ortho-C-H arylation of N,N-dialkylthiobenzamides with boronic acids. The method employs [RuCl2(p-cym)]2 in the presence of Cu(OTf)2 and Ag2O oxidant. The reaction represents the first example of Ru-catalyzed C-H arylation directed by sulfur-containing groups and a rare example of C-H arylation directed by the versatile thiobenzamide moiety. As a further advantage, the method is performed in sustainable and eco-friendly 2-MeTHF as a solvent.

Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)

Although highly effective for most amide syntheses, the activation of carboxylic acids requires the use of problematic coupling reagents and is often poorly suited for challenging cases such as N-methyl amino acids. As an alternative to both secondary and tertiary amides, we report their convenient synthesis by the rapid oxidation of trifluoroborate iminiums (TIMs). TIMs are easily prepared by acid-promoted condensation of potassium acyltrifluoroborates (KATs) and amines and are cleanly and rapidly oxidized to amides with hydrogen peroxide. The overall transformation can be conducted either as a one-pot procedure or via isolation of the TIM. The unique nature of the neutral, zwitterionic TIMs makes possible the preparation of tertiary amides via an iminium species that would not be accessible from other carbonyl derivatives and can be conducted in the presence of unprotected functional groups including acids, alcohols and thioethers. In preliminary studies, this approach was applied to the late-stage modifications of long peptides and the iterative synthesis of short, N-methylated peptides without the need for coupling agents.

Catalyst-Free, Metal-Free, and Chemoselective Transamidation of Activated Secondary Amides

A simple protocol, which is catalyst-free, metal-free, and chemoselective, for transamidation of activated secondary amides in ethanol as solvent under mild conditions is reported. A wide range of amines, amino acids, amino alcohols, and the substituents, which are problematic in catalyzed transamidation, are tolerated in this methodology. The transamidation reaction was successfully extended to water as the medium as well. The present methodology appears to be better than the other catalyzed transamidations reported recently.