28137-36-2

Usage

Preparation

Obtained by reaction of p-toluoyl chloride with anisole in the presence of –MoO2Cl2 (20 mol%),in refluxing acetonitrile for 20 h (3%) in refluxing methylene chloride for 20 h (1%).

InChI:InChI=1/C15H14O2/c1-11-7-9-12(10-8-11)15(16)13-5-3-4-6-14(13)17-2/h3-10H,1-2H3

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 100-66-3 methoxybenzene 
• 103224-67-5 2,3,4,5,6-pentamethylphenyl 4-tolyl ketone 
• 579-75-9 2-Methoxybenzoic acid 
• 108-88-3 toluene 
• 201230-82-2 carbon monoxide 
• 39248-93-6 4-methyl(thiobenzoic) acid S-(4-chlorophenyl) ester 
• 99-94-5 p-Toluic acid 
• 529-28-2 4-iodoanisol 
• 5720-05-8 4-methylphenylboronic acid 
• 126403-71-2 p-tolylzinc bromide 
• 624-31-7 4-tolyl iodide 
• 67-66-3 chloroform 
• 578-57-4 2-bromoanisole 

Downstream Products

• 19434-30-1 2-hydroxy-4'-methylbenzophenone 
• 1312210-95-9 C₁₈H₂₀O₂ 
• 1312210-91-5 C₁₈H₁₈O₂ 

Relevant academic research and scientific papers

Tetra- And Dinuclear Palladium Complexes Based on a Ligand of 2,8-Di-2-pyridinylanthyridine: Preparation, Characterization, and Catalytic Activity

Complexation of L [L = 5-phenyl-2,8-di-2-pyridinyl-anthyridine] with [Pd(CH3CN)4](BF4)2 and [Pd(CH3CN)3Cl](BF4) in a molar ratio of 1:2 rendered the corresponding dinuclear complexes [Pd2L (CH3CN)4](BF4)4 (1) and [Pd2L (CH3CN)2Cl2](BF4)2 (2), respectively. However, treatment of L with (COD)PdCl2 followed by anion exchange yielded a tetranuclear complex [Pd4L3Cl4](PF6)4(4a). Structures of these complexes are characterized by both spectroscopy and X-ray crystallography. Interconversion of these three complexes was studied via the manipulation of stoichiometric ratio of ligand to metal precursor. The catalytic activity of these complexes for carbonylative Suzuki-Miyaura cross-coupling was investigated. Complex 2 shows an excellent catalytic activity on the reaction of aryl iodide with arylboronic acid in the presence of atmospheric pressure of CO to give the corresponding benzophenones.

Sequential Organozinc Formation and Negishi Cross-Coupling of Amides Catalysed by Cobalt Salt

Herein, a cobalt-catalysed Negishi-type cross-coupling of amide derivatives is described. Apart from being the first example of cobalt-catalysed Negishi-type coupling of amides, the process described employs a unique, simple, and cheap catalytic system to perform both the organozinc formation and the Negishi-type coupling. Indeed, the same cobalt(II) bromide salt used to form the arylzinc species from aryl bromides is then re-used to perform the cross coupling of this resulting arylzinc with N-benzoyl glutarimides at room temperature. The main advantages of the reaction presented are its robustness and ease of use. Indeed, the reactions of organozinc formation and Negishi-type coupling are performed without precautions toward water or oxygen. (Figure presented.).

A general approach to intermolecular carbonylation of arene C-H bonds to ketones through catalytic aroyl triflate formation

The development of metal-catalysed methods to functionalize inert C-H bonds has become a dominant research theme in the past decade as an approach to efficient synthesis. However, the incorporation of carbon monoxide into such reactions to form valuable ketones has to date proved a challenge, despite its potential as a straightforward and green alternative to Friedel-Crafts reactions. Here we describe a new approach to palladium-catalysed C-H bond functionalization in which carbon monoxide is used to drive the generation of high-energy electrophiles. This offers a method to couple the useful features of metal-catalysed C-H functionalization (stable and available reagents) and electrophilic acylations (broad scope and selectivity), and synthesize ketones simply from aryl iodides, CO and arenes. Notably, the reaction proceeds in an intermolecular fashion, without directing groups and at very low palladium-catalyst loadings. Mechanistic studies show that the reaction proceeds through the catalytic build-up of potent aroyl triflate electrophiles.

Iron-catalyzed carbonylation of aryl halides with arylborons using stoichiometric chloroform as the carbon monoxide source

A general iron-catalyzed carbonylative Suzuki-Miyaura coupling of aryl halides with arylborons is reported, using stoichiometric CHCl3 as the CO source. The high efficiency, economy, selectivity, and operational simplicity of this transformation make this method a valuable tool in organic synthesis. Importantly, the presented strategy allows effective 13C labeling simply by using the commercially available 13C-labeled CHCl3. On the basis of the initial mechanistic exploration, an aryl radical intermediate is proposed in the present carbonylation process.

Efficient Synthesis of Diaryl Ketones by Nickel-Catalyzed Negishi Cross-Coupling of Amides by Carbon–Nitrogen Bond Cleavage at Room Temperature Accelerated by a Solvent Effect

The first Negishi cross-coupling of amides for the synthesis of versatile diaryl ketones by selective C?N bond activation under exceedingly mild conditions is reported. The cross-coupling was accomplished with bench-stable, inexpensive precatalyst [Ni(PPh3)2Cl2] that shows high functional-group tolerance and enables the synthesis of highly functionalized diaryl ketone motifs. The coupling occurred with excellent chemoselectivity favoring the ketone (cf. biaryl) products. Notably, this process represents the mildest conditions for amide N?C bond activation accomplished to date (room temperature, 10 min). Considering the versatile role of polyfunctional biaryl ketone linchpins in modern organic synthesis, availability, and excellent functional-group tolerance of organozinc reagents, this strategy provides a new platform for amide N?C bond/organozinc cross-coupling under mild conditions.

Diaryl ketone synthesis by [RuHCl(CO)(PPh3)3]- catalyzed coupling reaction of arylboronic acids with aryl aldehydes

[RuHCl(CO)(PPh3)3] was found to be an efficient catalyst for the coupling reaction of arylboronic acids with aryl aldehydes. The reaction proceeded smoothly in the presence of K2CO3 and H2O to give diaryl ketones in good yields. Diaryl ketones were obtained from primarily formed alcohols via Rucatalyzed transfer hydrogenation reaction.

SUBSTITUTED IMIDAZOLONE DERIVATIVES, PREPARATIONS AND USES

The present invention relates to polysubstituted imidazolone derivatives, to the pharmaceutical compositions comprising them and to the therapeutic uses thereof in the human and animal health fields. The present invention also relates to a process for preparing these derivatives.

Cesium hydroxide-promoted aerobic oxidation of sec-aromatic alcohols

A CsOH-promoted aerobic oxidation of sec-aromatic alcohols has been developed, using air as a free and clean oxidant, and providing aryl ketones in good to excellent yields.

Reactions of 2-hydroxybenzophenones with Corey-Chaykovsky reagent

A variety of 2-hydroxybenzophenones on reaction with Corey-Chaykovsky reagent underwent unprecedented rearrangements leading to 3-substituted benzofurans 8 and one-carbon homologated compounds 9 and 12. Compounds 9 could further be quantitatively transfor

Application of the catalytic friedel-crafts acylation reaction and regioselectivity correlations

A correlation was found between electronic properties and regioselectivity in the Friedel-Crafts reaction of substituted phenylacetic and benzoic acids with anisole, utilising substoichiometric (down to 1 mol%) amounts of catalyst. Relative reactivities of selected catalysts for this reaction were also studied. Georg Thieme Verlag Stuttgart.