2852-68-8

Usage

InChI:InChI=1/C15H14O/c1-11-5-3-7-13(9-11)15(16)14-8-4-6-12(2)10-14/h3-10H,1-2H3

Upstream product

• 591-17-3 meta-bromotoluene 
• 1711-06-4 3-Methylbenzoyl chloride 
• 201230-82-2 carbon monoxide 
• 2093-46-1 2-methylphenyl diazonium tetrafluoroborate 
• 937-01-9 trimethyl(3-methylphenyl)stannane 
• 10605-48-8 3,3'-(ethene-1,1-diyl)bis(methylbenzene) 
• 56-23-5 tetrachloromethane 
• 6482-39-9 sodium methyl carbonate 
• 625-95-6 3-Iodotoluene 
• 13939-06-5 molybdenum hexacarbonyl 
• 64-18-6 formic acid 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 98-86-2 acetophenone 
• 17933-03-8 m-tolylboronic acid 

Downstream Products

• 1583252-27-0 C₁₈H₁₈ 
• 1402416-28-7 N'-(di-m-tolylmethylene)-4-methylbenzenesulfonohydrazide 
• 1402416-21-0 butyl 2-(6-methyl-4-m-tolyl-2-tosyl-1,2-dihydrophthalazin-1-yl)acetate 

Relevant academic research and scientific papers

Palladium nanoparticles on amino-modified silica-catalyzed C–C bond formation with carbonyl insertion

Abstract: A practical and heterogeneously catalyzed Stille, homo-coupling, and Suzuki carbonylation reaction has been reported using Pd nanoparticles supported on amino-vinyl silica-functionalized magnetic carbon nanotube (CNT@Fe3O4@SiO2-Pd) for the efficient synthesis of symmetrical and unsymmetrical diaryl ketones from aryl iodides. A wide variety of symmetrical and unsymmetrical diaryl ketones were obtained in high yields under CO gas-free conditions using Mo(CO)6 as an efficient carbonyl source. Considering the atom economy of Ph3SnCl, less than an equimolar amount can be applied in Stille transformation, which is of great importance due to the toxicity of organotin derivatives. Moreover, no phosphine ligand and external reducing agent were necessary in these coupling carbonylation reactions. This heterogeneous Pd catalyst offers high activity with very low palladium leaching. Finally, the catalyst can be reused and recycled for six steps without loss in activity, exhibiting good example of sustainable methodology. Graphic abstract: [Figure not available: see fulltext.].

Photo-induced phosphorus radical involved semipinacol rearrangement reaction: Highly synthesis of γ-oxo-phosphonates

Hydroxyphosphoric acids display the unique biological activities, and they have some attractive prospects as clinical drug moleculars. Herein, a new approach for the synthesis of γ-oxo-phosphonates (the precursor of hydroxyphosphoric acid) has been established through the semipinacol rearrangement tactic involved the photo-induced phosphorus radical process. Most important, this transformation is avoid of the external oxidants, and occurs very well under the sunlight irradiation, meanwhile the γ-oxo-phosphonate was easily derivatized to obtain γ-hydroxyphosphoric acid, thus highlights the synthesis value of this method.

Sodium Methyl Carbonate as an Effective C1 Synthon. Synthesis of Carboxylic Acids, Benzophenones, and Unsymmetrical Ketones

Reported is the synthesis of carboxylic acids, symmetrical ketones, and unsymmetrical ketones with selectivity achieved by exploiting the differential reactivity of sodium methyl carbonate with Grignard and organolithium reagents.

Method for preparing symmetric diarylketone through catalytic oxidative carbonylation

The invention discloses a method for preparing symmetric diarylketone of a formula (I) as shown in the description. The method comprises the following steps: mixing arylboronic acid (II) (Ar-B(OH)2 (II)), a palladium catalyst, a promoter and an organic solvent in a reactor, introducing air and CO having a volume ratio of (7-19):1, reacting under the conditions of a pressure of 1-6 atm and a temperature of 30-80 DEG C for 8-16 hours, and performing after-treatment on the reaction solution, thereby obtaining the product symmetric diarylketone. According to the method disclosed by the invention,the air directly serves as an oxidizing agent to replace the O2 to be applied to oxidative carbonylation of the arylboronic acid, and the ratio of the air to CO is beyond an explosion limit. Therefore, the catalytic system is safe and economic. The palladium catalyst is small in dosage and simple in separation and can be recycled for several times. The method disclosed by the invention is mild inreaction condition, excellent in substrate suitability and high in yield.

Nickel-Catalyzed Molybdenum-Promoted Carbonylative Synthesis of Benzophenones

A nickel-catalyzed molybdenum-promoted carbonylative coupling reaction for the synthesis of benzophenones from aryl iodides has been developed. Various substituted diaryl ketones were synthesized in moderate to excellent yields under CO-gas-free conditions. A synergetic effect of both nickel and molybdenum has been observed, which is also responsible for the success of this transformation.

Palladium-Catalyzed Carbonylative Homocoupling of Aryl Iodides for the Synthesis of Symmetrical Diaryl Ketones with Formic Acid

A convenient method for the palladium-catalyzed carbonylative homocoupling of aryl iodides was developed. With formic acid as the CO source, various symmetrical diaryl ketones were synthesized in moderate to good yield in the presence of a palladium catalyst.

Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of N-Sulfinylimines and Benzimidates

C-H activation of arenes has been established as an important strategy for heterocycle synthesis via annulations between arenes and unsaturated coupling partners. However, nitriles failed to act as such a coupling partner. Dioxazolones have been employed as a synthon of nitriles, and subsequent coupling with arenes such as N-sulfinylimines and benzimidates bearing a functionalizable directing group provided facile access to two classes of quinazolines under Co(III)-catalysis.

Ligand-Free Palladium-Catalyzed Oxidative Carbonylative Homocoupling of Arylboron Reagents at Ambient Pressure

Arylboronic acids or potassium aryltrifluoroborates were readily oxidatively carbonylated to their corresponding diaryl ketones in high yields with high selectivities by ligand-free palladium-catalyzed homocoupling at atmospheric pressure. This novel method employs molecular oxygen or iodine as the oxidant and offers an attractive alternative to transition-metal-based oxidant systems.

One-pot synthesis of diarylmethanones through palladium-catalyzed sequential coupling and aerobic oxidation of aryl bromides with acetophenone as a latent carbonyl donor

A one-pot palladium-catalyzed synthesis of symmetrical and unsymmetrical diarylmethanones using acetophenone and aryl bromides as raw materials has been developed. In this reaction, acetophenone acts as a latent carbonyl donor and two pathways of palladium-catalyzed sequential coupling and aerobic oxidation are identified. The reaction is applicable to a spectrum of substrates and delivers the products in moderate to good yields. This method can be used for the synthesis of ketoprofen, a nonsteroidal anti-inflammatory drug, in a two-step procedure and 45% overall yield.

Palladium-catalyzed oxidative carbonylation for the synthesis of symmetrical diaryl ketones at atmospheric co pressure

A mild and efficient synthesis of symmetrical diaryl ketones by palladium-catalyzed oxidative carbonylation of arylboronic acids with carbon monoxide at atmospheric pressure is reported. Georg Thieme Verlag Stuttgart New York.