178323-47-2

Upstream product

• 611-94-9 4-Methoxybenzophenone 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 100-66-3 methoxybenzene 
• 4192-77-2 ethyl cinnamate 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 63164-96-5 ethyl 4-(2-phenylethynyl)benzoate 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 

Downstream Products

• 17684-11-6 3-(4-anisyl)cinnamic acid 
• 178323-48-3 (E)-3-(4-Methoxy-phenyl)-3-phenyl-prop-2-en-1-ol 
• 178323-59-6 N-tert-butoxycarbonyloxy-N-[3-(4-methoxyphenyl)-3-phenylallyl]carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Silver sequestration of halides for the activation of Pd(OAc)2 catalyzed Mizoroki-Heck reaction of 1,1 and 1,2 - Disubstituted alkenes

A ligand free catalytic system consisting of Pd(OAc)2 (cat) and stoichiometric quantities of silver salts, AgOAc or AgBF4, exhibit high efficiency in the Mizoroki-Heck arylation, transforming aryl iodides and 1,1 as well as 1,2 disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields in very short reaction times.

Palladium-catalyzed intramolecular amidation of C(sp2)-H bonds: Synthesis of 4-aryl-2-quinolinones

Figure presented A catalytic synthetic approach for the synthesis of 2-quinolinone compounds through a Pd-catalyzed C(sp2)-H functionalization/intramolecular amidation sequence is described. The cyclization process efficiently proceeds in the p

Palladium-catalyzed hydroarylation of alkynes with arenediazonium salts

The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with alkynes in the presence of triphenylsilane affords stereoselectively hydroarylation products in moderate to high yields. The reaction tolerates a variety of substituents including keto, ester, cyano, and nitro groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ. With ethyl phenylpropynoate as the starting alkyne, the hydroarylation affords ethyl (2)-2-arylcinnamates stereo- and regioselectively.

Mono- and β,β-double-heck reactions of α,β-unsaturated carbonyl compounds in aqueous media

Optimized reaction conditions for the mono- and β,β-diarylation of electron-deficient alkenes in aqueous media catalyzed either by a p-hydroxyacetophenone oxime-derived palladacycle or by palladium(II) acetate under phosphine-free conditions and in the presence of (dicyclohexyl)- methylamine as base are described. Regioselective monoarylation of unsubstituted and substituted α,β-unsaturated carbonyl compounds takes place with aryl iodides at 120 °C in water. Aqueous N,N-dimethylacetamide (DMA), tetra-n-butylammonium bromide (TBAB) as additive, and the palladacycle as catalyst are the most efficient conditions for the coupling with aryl bromides, good stereoselectivities being also obtained in the arylation of crotonates and itaconates, whereas cinnamic derivatives afford lower steroselectivity, with the exception of cinnamic acid and nitrile. β,β-Diarylation of unsubstituted α,β-unsaturated carbonyl compounds can be controlled by using higher loading of the palladacycle and can be performed in refluxing water for aryl iodides, whereas DMA must be used for aryl bromides. Microwave irradiation can be used in the monoarylation of tertbutyl acrylate with aryl iodides in water or the coupling between ethyl cinnamate and aryl bromides in aqueous DMA.

Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes

cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Heck reaction of disubstituted alkenes such as methyl crotonate, ethyl cinnamate, methyl methacrylate or α-methylstyrene with a variety of aryl halides. In the presence of 1,2-disubstituted alkenes the stereoselectivities of the reactions strongly depend on the substituents of the alkenes. Selectivities up to 97% in favor of E-isomers can be obtained for the addition to methyl crotonate. With the 1,1-disubstituted alkenes methyl methacrylate or α-methylstyrene mixtures of products are obtained.

Toward waste-free production of heck products with a catalytic palladium system under oxygen

A 100% carbon-efficient, halide- and solvent-free alternative for the synthesis of Heck-type products is the direct oxidative coupling of arenes with olefins, catalyzed by Pd(OAc)2 under oxygen (see scheme). The reactions can be performed under mild conditions, and water is the only by-product. (TON = turnover number, TOF = turnover frequency.).

New synthesis of isoxazolidines

A new synthesis of 5-substituted isoxazolidines was developed by direct isoxazolidine ring formation of allylic hydroxylamines under acidic conditions. The cyclization process is an electrophilic SN1 type reaction. The formed carbocation intermediate is stabilized by electron rich groups (i.e., phenyl). A moiety that mediates oxonium ion formation (i.e., para-methoxy) accelerates the rate of product formation.