4885-14-7

Upstream product

• 60-29-7 diethyl ether 
• 67075-69-8 2,3,5,6-Tetramethylbenzoyl chloride 
• 2674-04-6 diphenyl cadmium 
• 95-93-2 1,2,4,5-tetramethylbenzene 
• 98-88-4 benzoyl chloride 
• 4885-12-5 2'-bromo-2,3,5,6-tetramethyl-benzophenone 
• 5005-35-6 2-pyridyl benzoate 
• 4885-10-3 2'-methoxy-2,3,5,6-tetramethyl-benzophenone 
• 201230-82-2 carbon monoxide 
• 71-43-2 benzene 
• 36967-85-8 benzoyl triflate 
• 65-85-0 benzoic acid 
• 532-32-1 sodium benzoate 
• 591-50-4 iodobenzene 

Downstream Products

• 867132-37-4 (6-methyl-cyclohexa-1,3-dienyl)-(2,3,5,6-tetramethyl-phenyl)-ketone 
• 111028-85-4 4'-butyl-2,3,5,6-tetramethyl-benzophenone 
• 111029-36-8 2'-butyl-2,3,5,6-tetramethyl-benzophenone 
• 40910-15-4 4'-isopropyl-2,3,5,6-tetramethyl-benzophenone 
• 854038-23-6 2'-[2-(α-hydroxy-2,4,6-trimethyl-benzyl)-phenyl]-2,3,5,6-tetramethyl-benzophenone 
• 103331-70-0 2'-[2-(α-hydroxy-2,3,5,6-tetramethyl-benzyl)-phenyl]-2,3,5,6-tetramethyl-benzophenone 
• 135581-57-6 1,4-bis(2,3,5,6-tetramethylbenzoyl)benzene 
• 32363-48-7 4'-tert-butyl-2,3,5,6-tetramethyl-benzophenone 
• 33609-23-3 (4-tert-butyl-cyclohexa-1,5-dienyl)-(2,3,5,6-tetramethyl-phenyl)-ketone 
• 40940-77-0 2,3,5,6-tetramethyl-α-phenylbenzenemethanol 
• 40910-02-9 4-bromo-2,3,5,6-tetramethyl-benzophenone 
• 32102-77-5 phenyl(2,3,5,6-tetramethylphenyl)methane 
• 10387-14-1 2,4,5-trimethyl-isophthalic acid 
• 32665-12-6 1,4-dibenzoyl-2,3,5,6-tetramethyl-benzene 

Relevant academic research and scientific papers

A palladium-catalyzed C-H functionalization route to ketones: Via the oxidative coupling of arenes with carbon monoxide

We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Exploiting the latter can also allow the synthesis of unsymmetrical ketones from two different arenes.

Decarboxylation with Carbon Monoxide: The Direct Conversion of Carboxylic Acids into Potent Acid Triflate Electrophiles

We report a new strategy for the conversion of carboxylic acids into potent acid triflate electrophiles. The reaction involves oxidative carbonylation of carboxylic acids with I2 in the presence of AgOTf, and is postulated to proceed via acyl hypoiodites that react with CO to form acid triflates. Coupling this chemistry with subsequent trapping with arenes offers a mild, room temperature approach to generate ketones directly from broadly available carboxylic acids without the use of corrosive and reactive Lewis or Bronsted acid additives, and instead from compounds that are readily available, stable, and functional group compatible.

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.

Isolation, X-ray structures, and electronic spectra of reactive intermediates in Friedel-Crafts acylations

Reactive intermediates in the Friedel-Crafts acylation of aromatic donors are scrutinized upon their successful isolation and X-ray crystallography at very low temperatures. Detailed analyses of the X-ray parameters for the [1:1] complexes of different al

2-(Trifluoromethylsulfonyloxy)pyridine as a Reagent for the Ketone Synthesis from Carboxylic Acids and Aromatic Hydrocarbons

A new reagent 2-(trifluoromethylsulfonyloxy)pyridine (TFOP) was prepared by the reaction of sodium salt of 2-pyridinol with trifluoromethylsulfonyl chloride in dioxane.The conpound TFOP in trifluoroacetic acid has been found to intermolecularly dehydrate from benzoic acid and aromatic hydrocarbons to give the corresponding benzophenones in high yield.It was further elucidated, in the reaction of fluorene, that a variety of carboxylic acids can be used as the acyl precursor for the aromatic ketone synthesis in conjunction with the TFOP/TFA system.This acylation procedure has been applied to the synthesis of 2-acylthiophenes, which are hard to prepare in a satisfactory yield by the classical Friedel-Crafts reaction using aluminum chloride as the catalyst.

N-Acylimidazoles-Trifluoroacetic Acid System as the Acylating Agent for Aromatic Hydrocarbons

N-Benzoylimidazole in trifluoroacetic acid could benzoylate electron-rich aromatic compounds, such as durene, p-dimethoxybenzene, mesitylene, anisole, thiophene, and fluorene, to give the corresponding benzophenone derivatives in good yields.It was further elucidated, in the reaction of fluorene, that N-acylimidazoles composed of a variety of acyl groups also could be used for the ketone synthesis.Therein, the imidazolides of aliphatic carboxylic acids or substituted benzoic acid with an electron-donating group gave ketones in high yields.The above-mentioned aromaticcompounds were also acylated with N-trifluoroacetylimidazole and free carboxylic acids in trifluoroacetic acid.The mechanism for these reactions was assumed to proceed via a mixed anhydride between trifluoroacetic acid.