27645-60-9

Usage

Preparation

Obtained by reaction of 4-methoxybenzoyl chloride with acetonitrile in the –presence of aluminium chloride in carbon disulfide at r.t. for 3 h (35%).

InChI:InChI=1/C15H11NO2/c1-18-14-8-6-13(7-9-14)15(17)12-4-2-11(10-16)3-5-12/h2-9H,1H3

Upstream product

• 3058-39-7 4-iodobenzonitrile 
• 14271-83-1 4-methoxybenzoyl cyanide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 105-07-7 4-cyanobenzaldehyde 
• 623-00-7 4-bromobenzenecarbonitrile 
• 7099-91-4 p-methoxybenzoylformic acid 
• 201230-82-2 carbon monoxide 
• 174813-84-4 4-(hydroxy(4-methoxyphenyl)methyl)benzonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 696-62-8 para-iodoanisole 
• 126747-14-6 4-cyanophenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 52898-49-4 4,N-dimethoxy-N-methylbenzamide 
• 100-09-4 4-methoxybenzoic acid 

Downstream Products

• 30042-05-8 4-(diazo(4-methoxyphenyl)methyl)benzonitrile 
• 67205-87-2 4-(4-methoxy-benzoyl)-benzoic acid ethyl ester 
• 67205-88-3 ethyl 4-(4-methoxybenzyl) benzoate 
• 67205-89-4 4-(4-methoxybenzyl)benzoic acid 
• 67205-84-9 4-[4-(4-methoxybenzyl)benzyl]heptane-3,5-dione 
• 67205-85-0 4-[4-(4-hydroxybenzyl)benzyl]heptane-3,5-dione 
• 66938-67-8 4-(4-Amino-3-nitro-benzoyl)-benzonitrile 
• 118909-15-2 1-[2-hydroxy-3-propyl-4-({4-[4-(1H-tetrazol-5-yl)-benzoyl]phenoxy}methyl)phenyl]ethanone 
• 135312-33-3 4-[4-(4-Acetyl-3-hydroxy-2-propyl-benzyloxy)-benzoyl]-benzonitrile 

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.

Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization

Alkenes, ethers, and alcohols account for a significant percentage of bulk reagents available to the chemistry community. The petrochemical, pharmaceutical, and agrochemical industries each consume gigagrams of these materials as fuels and solvents each year. However, the utilization of such materials as building blocks for the construction of complex small molecules is limited by the necessity of prefunctionalization to achieve chemoselective reactivity. Herein, we report the implementation of efficient, sustainable, diaryl ketone hydrogen-atom transfer (HAT) catalysis to activate native C-H bonds for multicomponent dicarbofunctionalization of alkenes. The ability to forge new carbon-carbon bonds between reagents typically viewed as commodity solvents provides a new, more atom-economic outlook for organic synthesis. Through detailed experimental and computational investigation, the critical effect of hydrogen bonding on the reactivity of this transformation was uncovered.

Dirhodium-Catalyzed Enantioselective B?H Bond Insertion of gem-Diaryl Carbenes: Efficient Access to gem-Diarylmethine Boranes

The scarcity of reliable methods for synthesizing chiral gem-diarylmethine borons limits their applications. Herein, we report a method for highly enantioselective dirhodium-catalyzed B?H bond insertion reactions with diaryl diazomethanes as carbene precursors. These reactions afforded chiral gem-diarylmethine borane compounds in high yield (up to 99 % yield), high activity (turnover numbers up to 14 300), high enantioselectivity (up to 99 % ee) and showed unprecedented broad functional group tolerance. The borane compounds synthesized by this method could be efficiently transformed into diaryl methanol, diaryl methyl amine, and triaryl methane derivatives with good stereospecificity. Mechanistic studies suggested that the borane adduct coordinated to the rhodium catalyst and thus interfered with decomposition of the diazomethane, and that insertion of a rhodium carbene (generated from the diaryl diazomethane) into the B?H bond was most likely the rate-determining step.

Acyl radicals from α-keto acids using a carbonyl photocatalyst: Photoredox-catalyzed synthesis of ketones

Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridylstabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol is compatible with a wide range of functional groups.

Novel and efficient bridged bis(N-heterocyclic carbene)palladium(II) catalysts for selective carbonylative Suzuki–Miyaura coupling reactions to biaryl ketones and biaryl diketones

Bridged N,N′-substituted bisbenzimidazolium bromide salts (L1, L2, and L3) were synthesized and fully characterized. Reactions of palladium acetate with L1, L2, and L3 afforded corresponding new bridged bis(N-heterocyclic carbene)palladium(II) complexes (C1, C2, and C3) in high yields. The X-ray structure of complex C1 showed that the Pd(II) ion is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromido ligands are in the cis position, resulting in a distorted square planar geometry. The three Pd(NHC)2Br2 complexes C1, C2, and C3 were evaluated in carbonylative Suzuki–Miyaura coupling reactions of aryl boronic acids with aryl halides and displayed high catalytic activity with low catalyst loading. The coupling reactions of aryl bromides were selective towards the carbonylation product at higher carbon monoxide pressure.

Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N?C Cleavage

The direct transition-metal-free acylation of amides with functionalized Grignard reagents by highly chemoselective N?C cleavage under kinetic control has been accomplished. The method offers rapid and convergent access to functionalized biaryl ketones through transient tetrahedral intermediates. The direct access to functionalized Grignard reagents by in situ halogen–magnesium exchange promoted by the versatile turbo-Grignard reagent (iPrMgCl?LiCl) permits excellent substrate scope with respect to both the amide and Grignard coupling partners. These reactions enable facile, operationally simple and chemoselective access to tetrahedral intermediates from amides under significantly milder conditions than chelation-controlled intermediates. This novel direct two-component coupling sets the stage for using amides as acylating reagents in an alternative paradigm to the metal-chelated approach, acyl metals and Weinreb amides.

COMPOUNS, COMPOSITIONS AND METHODS OF USE

Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.

N-Acylsuccinimides: Efficient acylative coupling reagents in palladium-catalyzed Suzuki coupling via C–N cleavage

An acylative Suzuki coupling of activated amides with aryl boronic acids has been reported via palladium-catalyzed C–N bond cleavage. This protocol demonstrate amides can be activated by an atom-economic and cheap succinimide, which can be efficiently utilized to synthesize broad array of diaryl ketones in moderate to good yields.

Pd-ZnO nanowire arrays as recyclable catalysts for 4-nitrophenol reduction and Suzuki coupling reactions

In this work, we report a facile approach for the preparation of Pd nanoparticle-ZnO nanowire arrays followed by demonstrating their use as recyclable catalyst for reactions under different conditions. The facile synthesis largely relies on a spontaneous reduction of PdCl42? at the surface of oriented ZnO nanowires grown on a Zn foil. This is due to a combination of the strongly reducing ability of Zn foil and the semiconducting nature of ZnO nanowires. At room temperature and under a weak alkaline condition, the as-prepared Pd nanoparticle-ZnO nanowire arrays show a catalytic activity factor up to 76.6 s?1 g?1 in the reduction of 4-nitrophenol and no obvious decreases in the catalytic activity even after use of 10 times. Meanwhile, the as-prepared Pd nanoparticle-ZnO nanowire arrays exhibit extraordinary catalytic activity toward Suzuki and carbonylative Suzuki reactions at a higher temperature under a stronger alkaline condition. The outstanding performance of the hybrid nanowire arrays is mainly originated from the small size of the Pd nanoparticles (～2-4 nm) with clean surfaces, as well as a strong affinity between the Pd nanoparticles and ZnO nanowires, leading to marginable catalyst loss and aggregation. Considering the multiple choices of both noble metal nanocatalyst and transition metal oxide nanowire array, we expect noble metal nanoparticle-transition metal oxide nanowire arrays to be emerged as a new class of recyclable catalysts attractive for diverse organic reactions to develop pharmaceuticals, natural products and advanced functional materials.

At normal pressure fragrant ketone copper catalytic synthesis method

The invention discloses a method of synthesizing diaryl ketone under normal pressure by virtue of copper catalysis. The method is as follows: in a solvent alcohol or aqueous liquor of alcohol, under action of alkali and acid, adding a copper catalyst, alkyl iodide, alkyl boric acid and carbon monoxide to directly carry out crossed coupling reaction to prepare diaryl ketone compounds. According to the invention, the method of preparing diaryl ketone compounds by carbonylation Suzuki coupling reaction has the advantages as follows: the catalyst is wide in source, cheap and small in toxicity; the reaction is free of ligand in reaction and good in activity; the reaction is carried out under the normal pressure and selectivity is high; a substrate source is wide and stable; functional group compatibility is good and scope of application for the substrate is wide; a reaction medium is environment-friendly and recyclable. Under the condition of optimizing reaction conditions, the target product separating yield is 95%.