72233-10-4

Upstream product

• 21960-26-9 (4-methoxybenzylidene)triphenylphosphorane 
• 5344-23-0 diethoxyacetaldehyde 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 696-62-8 para-iodoanisole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1963-36-6 4-methoxycinnamaldehyde 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 82724-69-4 1-Methoxy-4-((1E,5E)-3,7,7-triethoxy-hepta-1,5-dienyl)-benzene 
• 89553-29-7 (E)-5-ethoxy-7-(p-methoxyphenyl)-2,6-heptadienal 
• 118326-21-9 1-((1E,5E)-3-Ethoxy-6-methyl-octa-1,5,7-trienyl)-4-methoxy-benzene 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 72232-59-8 (2E,4E,6E)-7-(4-methoxyphenyl)hepta-2,4,6-trienal 
• 1963-36-6 (Z)-3-(4-Methoxyphenyl)-2-propenal 
• 60682-78-2 3-(p-anisyl)-2,2-dichloro-1-diethoxymethylcyclopropane 
• 24056-44-8 C₁₈H₂₈O₄ 
• 1963-36-6 4-methoxycinnamaldehyde 
• 22767-72-2 ethyl 3-(4-methoxyphenyl)propanoate 
• 90714-17-3 3-(p-anisyl)-2,2-diphenylthio-1-formylcyclopropane 
• 90714-20-8 3-(p-anisyl)-2,2-diphenylthio-2,3-dihydrofuran 
• 90714-23-1 3-(p-anisyl)-2-phenylthiofuran 
• 90714-14-0 3-(p-anisyl)-1-formyl-2,2-dichlorocyclopropane 

Relevant academic research and scientific papers

Fluorous oxime palladacycle: A precatalyst for carbon-carbon coupling reactions in aqueous and organic medium

To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon-carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.

Identification of 5-arylidene-4-thiazolidinone derivatives endowed with dual activity as aldose reductase inhibitors and antioxidant agents for the treatment of diabetic complications

In continuing the search for more effective 5-arylidene-4-thiazolidinones as aldose reductase inhibitors, a new set of suitably substituted compounds (4, 5 and 8) was explored. Acetic acids 5, particularly 5a and 5h, proved to be interesting inhibitors of the enzyme as well as excellent antioxidant agents that are potentially able to counteract the oxidative stress associated with both diabetic complications as well as other pathologies. Molecular docking experiments supported SAR studies.

Synthesis, characterization and primary evaluation of the synthetic efficiency of supported vinyltins and allyltins

Supported vinyltins and allyltins grafted to an insoluble cross-linked polystyrene matrix were prepared using methods usually employed in solution, like hydrostannylation of alkynes, transmetallation of a tin halide with organomagnesium or organozinc reagents, and substitution of an allyl halide by a supported stannylanion or SN2′ substitution of a supported β-stannylacrolein acetal by cyanocopper reagents in the presence of boron trifluoride etherate. The insoluble grafted organotin reagents were analysed by HRMAS NMR, allowing an unambiguous assignment of their isomeric distribution or the identification of side products. When involved in Stille cross-coupling reactions (vinyltins) or in addition on aldehydes (allyltins), these supported reagents exhibit similar reactivity and similar stereoselectivity when compared to the tributyltin analogues, with the advantage to prevent problems due to the contamination by tin residues.

Evaluation of polymer-supported vinyltin reagents in the Stille cross-coupling reaction

The synthesis of two new vinyltin reagents grafted on an insoluble macroporous polymer is reported. These reagents were used in the palladium-catalyzed Stille cross-coupling reaction with aryl halides. In all reactions, the conversion of the starting aryl halide is high and the amount of organotin by-product is particularly low (at the end of the catalytic run, the amount of Sn is up to 16 ppm in the crude reaction mixture removed of the insoluble polymer, and it is less than 1 ppm in the product purified by chromatography on silica gel).

Chemoselective Heck arylation of acrolein diethyl acetal catalyzed by an oxime-derived palladacycle

A dimeric 4-hydroxyacetophenone oxime-derived palladacycle has been used as a very efficient precatalyst for the chemoselective arylation of acrolein diethyl acetal to give either cinnamaldehyde derivatives or 3-arylpropanoate esters by proper choice of the reaction conditions. The synthesis of cinnamaldehyde derivatives can be performed by Heck reaction of acrolein diethyl acetal with iodo-, bromo- or chloroarenes in N,N-dimethylacetamide (DMA) using K2CO3 as base at 120°C and tetra-n-butylammonium acetate (TBAA) and KCl as additives, followed by acid workup. In the case of 3-arylpropanoate esters the corresponding arylation of acrolein diethyl acetal with iodoarenes can be performed at 90°C in aqueous DMA using (dicylohexyl)methylamine as base, whereas for bromoarenes the reaction has to be performed at 120°C using tetra-n-butylammonium bromide (TBAB) as additive. Alternatively, this process can be performed under microwave irradiation. These couplings take place in good yields and with lower catalyst loading than with palladium(II) acetate as well as in shorter reaction times and with lower excess of acrolein diethyl acetal.

An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides

(Matrix presented) The reaction of aryl iodides and bromides with acrolein diethyl acetal in the presence of Pd(OAc)2, nBu 4NOAc, K2CO3, KCl, and DMF, at 90°C until the disappearance of the acetal followed by the addition of 2 N HCl to the crude reaction mixture, affords cinnamaldehydes in good to high yields. A variety of functional groups are tolerated in the aryl halides, including ether, aldehyde, ketone, ester, dialkylamino, nitrile, and nitro groups. The presence of substituents close to the oxidative addition site does not hamper the reaction.

3-arylpropanoate esters through the palladium-catalyzed reaction of aryl halides with acrolein diethyl acetal

The reaction of aryl halides with acrolein diethyl acetal in the presence of Pd(OAc)2, n-Bu3N, and n-Bu4NCl in DMF at 90°C affords ethyl 3-arylpropanoates. A variety of functional groups are tolerated in the aryl halides, including ether, aldehyde, ketone, ester, nitrile, and nitro groups. ortho-Substituents do not hamper the reaction. 3-Arylpropanoate esters were isolated in good to excellent yields with many neutral, electron-rich and electron-poor aryl iodides and electron-poor aryl bromide. Neutral and electron-rich aryl bromides gave the desired ester in moderate yields.

Reactions with Phosphine Alkylenes, 44. A Further Synthesis of (Z)-α,β-Unsaturated Aldehydes

Reaction of phosphorus ylides 4, especially such with electron donating groups R, with the glyoxal semiacetal 5 leads Z-stereospecifically to the formation of the acetals 3, which can be cleaved to the (Z)-α,β-unsaturated aldehydes 6.