53780-25-9

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 122-78-1 phenylacetaldehyde 
• 1392470-62-0 2-(2-methylphenyl)-2-phenyloxirane 
• 197230-95-8 N,N-dimethyl-2-[2-(phenyl)ethenyloxy]ethanamine 
• 591-50-4 iodobenzene 
• 7664-93-9 sulfuric acid 

Downstream Products

• 131029-27-1 Z-(R)-1-[2-[[2-(2-Methylphenyl)-2-phenylethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester 
• 131029-29-3 E-(R)-1-[2-[[2-(2-Methylphenyl)-2-phenylethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Rhenium complex-catalyzed Meinwald rearrangement reactions of oxiranes

The Meinwald rearrangement reaction of oxiranes to the corresponding carbonyl compounds is efficiently catalyzed by the ReBr(CO)5 complex.

Highly selective palladium-catalyzed direct c-h α-monoarylation of carbonyl compounds using water containing the surfactant polyoxyethylene- α-tocopheryl sebacate (PTS) as a solvent

Highly selective direct C-H α-monoarylation reactions of 4-chromanones, ketones and 2-phenylacetaldehyde with aryl halides have been performed in satisfactory yields by using a tris(dibenzylideneacetone) dipalladium(0)/tri-tert-butylphosphine tetrafluoroborate catalyst system, potassium bicarbonate as the base and a solvent consisting of pure water containing a small amount of polyoxyethylene-α-tocopheryl sebacate (PTS). Analogous reaction conditions have been employed in a tandem process leading to phenyl-substituted isocoumarins from carbonyl compounds and methyl 2-bromobenzoate.

Highly regioselective, sequential, and multiple palladium-catalyzed arylations of vinyl ethers carrying a coordinating auxiliary: An example of a heck triarylation process

This article describes the development of new auxiliary-accelerated Heck multiarylations by intramolecular presentation of the oxidative addition complex. The introduction of a specific, palladium-coordinating dimethylamino group allows for the desired chelation-accelerated and chelation-controlled tri- and diarylation reactions. We report (a) the first example of a Heck triarylation process, (b) highly selective palladium-catalyzed diarylations of alkyl vinyl ethers, and (c) a very rapid two-phase protocol for the microwave-assisted hydrolysis of amino-substituted, arylated vinyl ethers constituting an entry to diarylated ethanals and substituted desoxybenzoins. X-ray structures and product patterns support the suggested substrate-controlled Heck reaction pathway. The catalyst-directing alkyl dimethylamino functionality was rapidly (1-2 min) and efficiently released by microwave hydrolysis after Heck multiarylation reactions. The liberated aromatic carbonyl compounds were thereafter isolated and fully characterized.