6337-70-8

Upstream product

• 2021-28-5 ethyl dihydrocinnamate 
• 75-36-5 acetyl chloride 
• 27374-25-0 [(1-Ethoxycyclopropyl)oxy]trimethylsilane 
• 99-90-1 para-bromoacetophenone 
• 911641-23-1 bis(2-carboethoxyethyl)zinc 
• 104089-16-9 2-ethoxycarbonyethylzinc iodide 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 13329-40-3 4-Iodoacetophenone 
• 140-88-5 ethyl acrylate 
• 64-17-5 ethanol 
• 127921-76-0 (E)-3-(4-acetylphenyl)acrylaldehyde 
• 539-74-2 Ethyl 3-bromopropionate 
• 99-91-2 para-chloroacetophenone 
• 98-86-2 acetophenone 

Downstream Products

• 91671-15-7 methyl 3-(4-acetylphenyl)propionate 
• 39105-51-6 3-(4-acetylphenyl)propionic acid 

Relevant academic research and scientific papers

One-Pot, Tandem Wittig Hydrogenation: Formal C(sp3)-C(sp3) Bond Formation with Extensive Scope

A one-pot, tandem Wittig hydrogenation of aldehydes with stabilized ylides is reported, representing a formal C(sp3)-C(sp3) bond construction. The tandem reaction operates under mild conditions, is high yielding, and is broad in scope. Chemoselectivity for olefin reduction is observed, and the methodology is demonstrated in the synthesis of lapatinib analogues and a formal synthesis of (±)-cuspareine. Early insights suggest that the chemoselectivity observed in the reduction step is due to partial poisoning of the catalyst, after step one, thus adding to the power of the one-pot procedure.

Plasma synthesis of oxidized graphene foam supporting Pd nanoparticles as a new catalyst for one-pot synthesis of dibenzyls

We have developed an environmentally-friendly method for the synthesis of Pd nanoparticle (Pd NPs) decorated different graphene supports, and the morphology and structure of the hybrids are characterized by transmission electron microscopy, X-ray diffraction, X-ray photoelectron spectroscopy and elemental mappings. Four hybrid materials based on graphene foam (GF), oxidized graphene foam (OGF), graphene oxide (GO) and reduced graphene oxide (RGO) have been used to catalyze Heck coupling reactions, and the effect of support on the activity of the hybrid material has been studied. Our results have revealed that Pd NP decorated OGF (Pd/OGF) is the most active catalyst, showing better performance than the commercial Pd/C catalyst. More importantly, the Pd/OGF catalyst has been successfully used for one-pot synthesis of dibenzyls with different aryl bromides and olefins, which has simplified the separation and purification process and realized a green organic synthesis process. This journal is

Direct synthesis of ester-containing indium homoenolate and its application in palladium-catalyzed cross-coupling with aryl halide

An efficient method for the synthesis of ester-containing indium homoenolate via a direct insertion of indium into β-halo ester in the presence of CuI/LiCl was described. The synthetic utility of the indium homoenolate was demonstrated by palladium-cataly

Direct method for carbon-carbon bond formation: The functional group tolerant cobalt-catalyzed alkylation of aryl halides

(Figure Presented). A new protocol for the direct cobaltcatalyzed alkylation of aryl halides has been developed that proceeds smoothly in the presence of phosphanes or bipyridines as ligands with a variety of alkyl halides, including challenging alkyl electrophiles bearing β hydrogen atoms (see scheme). Sensitive functional groups are tolerated on both coupling partners, thus, significantly extending the general scope of transition-metal-catalyzed alkylation of aryl halides.

CoBr2(Bpy): An efficient catalyst for the direct conjugate addition of aryl halides or triflates onto activated olefins

An efficient cobalt-catalyzed method devoted to the direct conjugate addition of functionalized aryl compounds onto Michael acceptors is described. The CoBr2(2,2′-bipyridine) complex appears to be an extremely suitable catalyst for the activation of a variety of aromatic reagents ranging from halides to triflates functionalized by reactive groups. This procedure allows for the synthesis of compounds resulting from 1,4-addition in good to excellent yields. The versatility of this original process represents a simple alternative to most known methods using organometallic reagents.

Facile preparation of organozinc bromides using electrogenerated highly reactive zinc and its use in cross-coupling reaction

Highly reactive zinc was readily prepared by electrolysis of a DMF solution containing pyrene as a mediator with a platinum cathode and a zinc anode. Preferential reduction of pyrene occurred to generate the corresponding radical anion, which reduced zinc ions generated from anodic dissolution to give zero valent zinc with high reactivity. The reactive zinc was successfully used for an efficient transformation of bromoalkanes into the corresponding organozinc bromides. Organozinc bromides obtained were further used successfully in Pd-catalyzed cross-coupling reaction with various aryl iodides and bromides.

Catalytic generation of activated carboxylates from enals: A product-determining role for the base

(Chemical Equation Presented) N-Heterocycle carbenes generated in situ from imidazolium or triazolium salts and bases react with enals, leading to the catalytic generation of homoenolates. The fate of these intermediates is determined by the catalytic base: strong bases such as tBuOK lead to carbon-carbon bond formation, while weaker bases allow protonation of the homoenolate and subsequent generation of activated carboxylates. This discovery, along with the design of a new triazolium precatalyst, enables the catalytic, atom-economical redox esterification of enals.

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.

Direct synthesis of 3-arylpropionic acids by tetraphosphine/palladium catalysed Heck reactions of aryl halides with acrolein ethylene acetal

Through the use of [PdCl(C3H5)]2/Cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides undergoes Heck reaction with acrolein ethylene acetal. With this acetal, the selective formation of 3-arylpropionic acids/esters was observed. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides. Graphical Abstract.

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.