197230-95-8

Upstream product

• 591-50-4 iodobenzene 
• 3622-76-2 (2-ethenyloxyethyl)dimethylamine 

Downstream Products

• 122-78-1 phenylacetaldehyde 
• 101-49-5 2-(benzyl)-1,3-dioxolane 
• 364796-66-7 N,N-dimethyl-2-[2-(4-acetylphenyl)-2-phenylethenyloxy]ethanamine 
• 1282534-46-6 2-(1,2-di(4-trifluoromethylphenyl)-2-phenylethoxy)-N,N-dimethylethanamine 
• 1282534-43-3 2-(1,2,2-triphenylethoxy)-N,N-dimethylethanamine 
• 1282534-44-4 2-(1,2-di(4-acetylphenyl)-2-phenylethoxy)-N,N-dimethylethanamine 
• 53780-25-9 2-(2-methylphenyl)-2-phenylacetaldehyde 
• 50600-30-1 2-(4-methylphenyl)-2-(phenyl)acetaldehyde 

Relevant academic research and scientific papers

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.

Chelation-Controlled, Palladium-Catalyzed Arylation of Vinyl Ethers

Chelation-controlled, palladium-catalyzed arylation of vinyl ethers with nitrogen-containing directing groups has been studied.Ethenyloxyalkylamines 1a-c and pyridines 2a-d, representing different carbon tethers were reacted with iodobenzene 4a and 1-iodonaphthalene 4b under phase-transfer conditions.The regioselectivity achieved is compared with the outcome from reactions with sterically similar vinyl ethers 3a-d.Arylations of the dimethylamine derivative 1a and the pyridine derivative 2a occurred at the terminal position of the olefins and were highly regioselective.A catalytic cycle for the regioselective, chelation-controlled vinylic substitution, involving a six-membered chelate ring, is proposed.