52980-99-1

Upstream product

• 623-12-1 4-chloromethoxybenzene 
• 874-60-2 4-methyl-benzoyl chloride 
• 116544-78-6 (5-chloro-2-hydroxyphenyl)(p-tolyl)methanone 
• 15023-58-2 4-chlorophenyl 4-methylbenzoate 
• 201230-82-2 carbon monoxide 
• 624-31-7 4-tolyl iodide 

Relevant academic research and scientific papers

Infrared study of polysubstitution effects in benzophenones and acetophenones: contribution of inter and intracycle interaction mechanisms

The carbonyl stretching frequencies of substituted 2-Me, 2,6-diMe, 2-MeO benzophenones and 2-Me, 2-MeO acetophenones have been measured in diluted CCl4 solutions.Two interaction mechanisms are observed.In X, Y substituted benzophenones with X on the same cycle as the ortho group and Y on the other cycle, it is shown that for X=Y, the effect of Y is greater than that of X except for very strong electron-releasing substituents.In this last case, the observed enhancement is attributed to the joint effects of intercycle interactions excercised on X and Y and of intracycle interaction on X.These results are corroborated by the study of substituted acetophenones in which only the intracycle mechanism can play a role.

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.

ACYLATION OF CHLOROANISOLES

In the reaction of 2-, 3-, and 4-chloroanisoles with the chlorides and anhydrides of acetic, propionic, and 4-substituted benzoic acids in the presence of 1E-3 mole of ferric chloride 35-80percent of the ketone fraction was obtained.Under the reaction con