cas 22767-72-2, 3-(4-METHOXY-PHENYL)-PROPIONIC ACID ETHYL ESTER

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Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes
Cross-electrophile coupling reactions of two Csp3-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.
Chen, Pan-Pan,Hong, Xin,Jarvo, Elizabeth R.,McGinnis, Tristan M.,Sanford, Amberly B.,Thane, Taylor A.
supporting information

(2020/03/23)

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.
Devlin, Rory,Jones, David J.,Mcglacken, Gerard P.
supporting information
p. 5223 - 5228
(2020/07/14)

Method for preparing organic carboxylic ester through combined catalysis of aryl bidentate phosphine ligand
The invention discloses a method for preparing organic carboxylic ester by combined catalysis of an aryl bidentate phosphine ligand. The method comprises the following steps: under the action of a palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, carrying out a hydrogen esterification reaction on terminal olefin, carbon monoxide and alcohol so as to generate theorganic carboxylic ester with one more carbon than olefin. According to the invention, by adoption of the palladium compound/aryl bidentate phosphine ligand/acidic additive combined catalyst, good catalytic activity and selectivity for the hydrogen esterification reaction of the olefin are achieved, and olefin carbonylation to synthesize organic carboxylic ester can be efficiently catalyzed. Thearyl bidentate phosphine ligand has a rigid skeleton structure of a rigid ligand and the flexibility of a flexible ligand, so the aryl bidentate phosphine ligand has proper flexibility due to the characteristic that the aryl bidentate phosphine ligand is soft and rigid, and a most favorable coordination mode and a stable active structure in space are favorably formed. In addition, the aryl bidentate phosphine ligand has the advantages of high stability, simple and convenient synthesis method and the like; and a novel industrial technology is provided for production of organic carboxylate compounds.
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Paragraph 0049

(2020/05/29)

Base-Free Iron Catalyzed Transfer Hydrogenation of Esters Using EtOH as Hydrogen Source
Herein, we report on the use of the iron pincer complex Iron-MACHO-BH, in the base-free transfer hydrogenation of esters with EtOH as a hydrogen source. More than 20 substrates including aromatic and aliphatic esters and lactones were reduced affording the desired primary alcohols and diols with moderate to excellent isolated yields. It is also possible to reduce polyesters to the diols with this method, enabling a novel way of plastic recycling. Reduction of the renewable substrate methyl levulinate proceeds to form 1,4-pentanediol directly. The yields are largely governed by the equilibrium between the alcohol and the ethyl ester.
Farrar-Tobar, Ronald A.,Wozniak, Bartosz,Savini, Arianna,Hinze, Sandra,Tin, Sergey,de Vries, Johannes G.
supporting information
p. 1129 - 1133
(2019/01/04)

Selective hydrogenation of α,β-unsaturated carbonyl compounds on silica-supported copper nanoparticles
Silica-supported copper nanoparticles prepared via surface organometallic chemistry are highly efficient for the selective hydrogenation of various α,β-unsaturated carbonyl compounds yielding the corresponding saturated esters, ketones, and aldehydes in the absence of additives. High conversions and selectivities (>99%) are obtained for most substrates upon hydrogenation at 100-150 °C and under 25 bar of H2.
Mendes-Burak, Jorge,Ghaffari, Behnaz,Copéret, Christophe
supporting information
p. 179 - 181
(2019/01/04)

Near-infrared fluorescence probes to detect reactive oxygen species for keloid diagnosis
Development of molecular probes for the detection of reactive oxygen and nitrogen species (RONS) is important for the pathology and diagnosis of diseases. Although an abnormally high RONS level has been identified in keloids-a benign dermal tumour develop
Cheng, Penghui,Zhang, Jianjian,Huang, Jiaguo,Miao, Qingqing,Xu, Chenjie,Pu, Kanyi
p. 6340 - 6347
(2018/08/12)

A Dual-Modal Molecular Probe for Near-Infrared Fluorescence and Photoacoustic Imaging of Peroxynitrite
Peroxynitrite (ONOO-), a reactive and short-lived biological oxidant, is closely related with many pathological conditions such as cancer. However, real-time in vivo imaging of ONOO- in tumors remains to be challenging. Herein, we de
Zhang, Jianjian,Zhen, Xu,Zeng, Jianfeng,Pu, Kanyi
p. 9301 - 9307
(2018/07/05)

Copper(i)-catalysed transfer hydrogenations with ammonia borane
Highly Z-selective alkyne transfer semihydrogenations and conjugate transfer hydrogenations of enoates can be effected by employing a readily available and air-stable copper(i)/N-heterocyclic carbene (NHC) complex, [IPrCuOH]. As an easy to handle and potentially recyclable H2 source, ammonia borane (H3NBH3) is used.
Korytiaková, Eva,Thiel, Niklas O.,Pape, Felix,Teichert, Johannes F.
supporting information
p. 732 - 735
(2017/01/13)

Isoprenoid Biosynthesis Inhibitors Targeting Bacterial Cell Growth
We synthesized potential inhibitors of farnesyl diphosphate synthase (FPPS), undecaprenyl diphosphate synthase (UPPS), or undecaprenyl diphosphate phosphatase (UPPP), and tested them in bacterial cell growth and enzyme inhibition assays. The most active compounds were found to be bisphosphonates with electron-withdrawing aryl-alkyl side chains which inhibited the growth of Gram-negative bacteria (Acinetobacter baumannii, Klebsiella pneumoniae, Escherichia coli, and Pseudomonas aeruginosa) at ～1–4 μg mL?1levels. They were found to be potent inhibitors of FPPS; cell growth was partially “rescued” by the addition of farnesol or overexpression of FPPS, and there was synergistic activity with known isoprenoid biosynthesis pathway inhibitors. Lipophilic hydroxyalkyl phosphonic acids inhibited UPPS and UPPP at micromolar levels; they were active (～2–6 μg mL?1) against Gram-positive but not Gram-negative organisms, and again exhibited synergistic activity with cell wall biosynthesis inhibitors, but only indifferent effects with other inhibitors. The results are of interest because they describe novel inhibitors of FPPS, UPPS, and UPPP with cell growth inhibitory activities as low as ～1–2 μg mL?1.
Desai, Janish,Wang, Yang,Wang, Ke,Malwal, Satish R.,Oldfield, Eric
p. 2205 - 2215
(2016/10/22)

Imidazole derivatives as accelerators for ruthenium-catalyzed hydroesterification and hydrocarbamoylation of alkenes: Extensive ligand screening and mechanistic study
Imidazole derivatives are effective ligands for promoting the [Ru3(CO)12]-catalyzed hydroesterification of alkenes using formates. Extensive ligand screening was performed to identify 2-hydroxymethylated imidazole as the optimal ligand. Neither carbon monoxide gas nor a directing group was required, and the reaction also showed a wide substrate generality. The Ru-imidazole catalyst system also promoted intramolecular hydrocarbamoylation to afford lactams. A Ru-imidazole complex was unambiguously analyzed by X-ray crystallography, and it had a trinuclear structure derived from one [Ru3(CO)12] and two ligands. This complex was also successfully used for hydroesterification. The mechanism was examined in detail by using D- and 13C-labeled formates, indicating that the hydroesterification reaction proceeds by a decarbonylation-recarbonylation pathway. Effective imidazole assistant: [Ru3(CO)12]-catalyzed hydroesterification of alkenes by using formates is drastically accelerated by imidazole derivatives and exhibits a broad substrate scope for both alkenes and formates. The Ru-imidazole complex also catalyzes the intramolecular hydrocarbamoylation of alkenes.
Konishi, Hideyuki,Muto, Takashi,Ueda, Tsuyoshi,Yamada, Yayoi,Yamaguchi, Miyuki,Manabe, Kei
p. 836 - 845
(2015/03/14)

Acid catalyzed rearrangement of vinyl and ketene acetals
Substituted vinyl and ketene acetals undergo smooth oxygen-to-carbon rearrangement with a catalytic amount of TMSOTf to afford chain-extended ketones or esters, respectively. The developed procedure has been applied to the stereoselective synthesis of C-glycosides from the corresponding anomeric vinyl ethers.
Maziarz, Elzbieta,Furman, Bart?omiej
p. 1651 - 1658
(2014/02/14)

Base directed palladium catalysed Heck arylation of acrolein diethyl acetal in water
The selective Heck arylation of acrolein diethyl acetal catalysed by [Pd(NH3)4]Cl2 in the presence of RAME-β-CD in water as solvent is described. Depending on the base (i.e. NaOAc or HN(i-Pr)2) good to high selectivity's towards, respectively, the cinnamaldehydes 2 or the 3-arylpropionic esters 1 were achieved. The results support that depending on the base different palladium intermediate complexes are formed. Using NaOAc, {[ArPdX(H2O)2]} complex is preferentially generated giving the cinnamaldehyde 2. On the other hand, in the presence of HN(i-Pr)2, a L-type ligand, [ArPdX(HN(i-Pr) 2(H2O)] or [ArPdX(HN(i-Pr)2(HN(i-Pr) 2)] will be generated leading to the formation of the 3-arylpropionic ester 1. For the last, coordinated amine participates very probably to the formation of the esters through intramolecular syn β-H elimination.
Al-Maksoud, Walid,Menuel, Stéphane,Jahjah, Mohamad,Monflier, Eric,Pinel, Catherine,Djakovitch, Laurent
p. 250 - 258
(2013/11/19)

The unexpected kinetic effect of enzyme mixture: The case of enzymatic esterification
During the studies towards synthesis of carboxylic acids esters, using ethyl carbonate and carboxylic acid as substrates, we found that different single enzyme systems provide model ethyl 3-phenylpropanoate in very low yield. Systematic studies proved tha
Zysk, Malgorzata,Zadlo, Anna,Brodzka, Anna,Wisniewska, Catalina,Ostaszewski, Ryszard
p. 225 - 229
(2014/04/03)

Heteroatom-free arene-cobalt and arene-iron catalysts for hydrogenations
75 years after the discovery of hydroformylation, cobalt catalysts are now undergoing a renaissance in hydrogenation reactions. We have evaluated arene metalates in which the low-valent metal species is - conceptually different from heteroatom-based ligands - stabilized by π coordination to hydrocarbons. Potassium bis(anthracene)cobaltate 1 and -ferrate 2 can be viewed as synthetic precursors of quasi-"naked" anionic metal species; their aggregation is effectively impeded by (labile) coordination to the various π acceptors present in the hydrogenation reactions of unsaturated molecules (alkenes, arenes, carbonyl compounds). Kinetic studies, NMR spectroscopy, and poisoning studies of alkene hydrogenations support the formation of a homogeneous catalyst derived from 1 which is stabilized by the coordination of alkenes. This catalyst concept complements the use of complexes with heteroatom donor ligands for reductive processes. Especially high selectivities were observed in the hydrogenation of various alkenes, ketones, and imines with bis(anthracene) cobaltate(-I) [K(dme)2{Co(C14H10)2}] under mild conditions (1-5 mol% cat., 1-10 bar H2, 20-60°C). Mechanistic studies indicate the operation in alkene hydrogenations of a homogeneous catalyst formed by initial ligand exchange and stabilized by the coordination of π-acidic alkenes or arenes.
Gaertner, Dominik,Welther, Alice,Rad, Babak Rezaei,Wolf, Robert,Von Wangelin, Axel Jacobi
p. 3722 - 3726
(2014/04/17)

Discovery of synthetic methoxy-substituted 4-phenylbutyric acid derivatives as chemical chaperones
In this study, we evaluated the chemical chaperone activity of synthetic 4-phenylbutyric acid (4-PBA) derivatives. These derivatives have a methoxy group at the benzene ring and/or longer or shorter fatty acid portions. Several 4-PBA derivatives demonstrated higher antiaggregation activity than 4-PBA. Moreover, 4-(4-methoxyphenyl)butanoic acid (7b) showed protective effects against endoplasmic reticulum stress-induced neuronal cell death.
Mimori, Seisuke,Okuma, Yasunobu,Kaneko, Masayuki,Kawada, Koichi,Nomura, Yasuyuki,Murakami, Yasuoki,Hamana, Hiroshi
p. 1051 - 1052
(2013/09/24)

A facile synthesis of 2h-chromenes and 9-functionalized phenanthrenes through reactions between α,β-unsaturated compounds and arynes
Facile syntheses of 2H-chromenes or 9-functionalized phenanthrenes under mild conditions in moderate to good yields have been developed. They each involve annulations of arynes with α,β-unsaturated compounds bearing different electron-withdrawing groups (EWGs). Depending on the natures of the different EWGs, the reactions proceed by different pathways: enals react with arynes through a tandem [2+2] cycloaddition/thermal electrocyclic ring-opening/6e-electrocyclization sequence to afford 2H-chromenes, whereas acyl-/ethoxycarbonyl-/cyano-substituted styrenes undergo Diels-Alder reactions with arynes followed by aromatization to afford 9-functionalized phenanthrenes. The scope, limitations, regioselectivities and mechanisms have been studied and are discussed in detail. Depending on the natures of different EWGs in α,β-unsaturated compounds, the reactions between arynes and α,β-unsaturated compounds proceed by different tandem pathways to afford either 2H-chromenes or 9-functionalized phenanthrenes in a selective manner, which is of potential pharmaceutical interest.
Zhang, Tiexin,Huang, Xian,Wu, Luling
experimental part
p. 3507 - 3519
(2012/07/30)

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.
Susanto, Woen,Chu, Chi-Yuan,Ang, Wei Jie,Chou, Tzyy-Chao,Lo, Lee-Chiang,Lam, Yulin
experimental part
p. 2729 - 2742
(2012/05/21)

Assembly and post-modification of a metal-organic nanotube for highly efficient catalysis
A metal-organic nanotube (MONT) was synthesized by linking up the bent organic ligands and the tetra-coordinated zinc cations under mild conditions. Structural analysis revealed that the MONT has a very large exterior wall diameter of 4.91 nm and an interior channel diameter of 3.32 nm. Interlocking of the nanotubes gives rise to a 3D chiral framework containing 1D helical cylindered channels with diameter of 2.0 nm. The MONT has very interesting property by synergizing the functionality of nanotubes, metal-organic frameworks (MOFs), and N-heterocyclic carbenes (NHCs). The dye adsorption experiments demonstrate that the channels of the MONTs are accessible to large reagents typically used for catalysis. The postmodification of the MONT can be easily operated by unmarking the imidazolium moieties in the channel walls, which was conducted as a highly active heterogeneous catalyst for Suzuki-Miyaura and Heck coupling reactions, hydrogenation of olefins and nitrobenzene, while the constituent elements are less efficient for these reactions under the same conditions.
Kong, Guo-Qiang,Ou, Sha,Zou, Chao,Wu, Chuan-De
p. 19851 - 19857
(2013/02/22)

Mild method for the selective esterification of carboxylic acids based on the Garegg-samuelsson reaction
A mild method for the selective esterification of primary alcohols is described. The use of different phosphines, I2, and imidazole allows the selective esterification of a wide variety of acids with excellent results. The generation of a bulky phosphonium-carboxylate salt as intermediate could justify the selectivity observed in this process. Additionally, amides also can be synthesized with use of this method.
Morcillo, Sara P.,Alvarez De Cienfuegos, Luis,Mota, Antonio J.,Justicia, Jose,Robles, Rafael
experimental part
p. 2277 - 2281
(2011/05/19)

GSK-3BETA INHIBITOR
For the purpose of providing a GSK-3β inhibitor containing a 2-aminopyridine compound or a salt thereof or a prodrug thereof useful as an agent for the prophylaxis or treatment of a GSK-3β-related pathology or disease, the present invention provides a GSK-3β inhibitor containing a compound represented by the formula (IA): wherein each symbol is as defined in the specification. or a salt thereof or a prodrug thereof.
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(2011/04/13)

Magnesium-induced regiospecific C-silylation of suitably substituted enoates and dienoates
The β-aryl-β-silyl and β,β-disilyl propionates have been synthesized from cinnamates and β-silyl acrylates by a regiospecific reductive C-silylation using Mg/silyl chloride/DMF system at room temperature. These reductive C-silylation conditions have also been applied to δ-aryl substituted dienoates wherein silylation took place at the δ-position leading to the synthesis of single regioisomeric allylsilanes with very high stereoselectivity.
Kundu, Pintu K.,Ghosh, Sunil K.
experimental part
p. 8562 - 8568
(2010/11/05)

Synthesis of aculeatins A and B via iterative hydrolytic kinetic resolution
A simple and concise approach for the synthesis of aculeatins A and B starting from (±)-epichlorohydrin is described. The synthetic strategy features Jacobsen's hydrolytic kinetic resolution and a Linchpin coupling as key steps. Georg Thieme Verlag Stuttgart.
Harbindu, Anand,Kumar, Pradeep
scheme or table
p. 1479 - 1484
(2010/10/18)

Hydrogenation of BF2 complexes with 1,3-dicarbonyl ligands
The catalytic hydrogenation (H2, Pd/C) of a set of BF2 complexes with a 1,3-dicarbonyl structural unit leading to monocarbonyl compounds has been studied. The transformation presented is general for the aryl-substituted derivatives and occurs under mild conditions (H2, 1 bar, 25 °C) in methanol or THF.
?tefane, Bogdan,Polanc, Slovenko
experimental part
p. 2339 - 2343
(2009/07/18)

Acrolein diethyl acetal: A three-carbon homologating reagent for the synthesis of β-arylpropanoates and cinnamaldehydes by heck reaction catalyzed by a Kaiser oxime resin derived palladacycle
A polymer palladacycle derived from Kaiser oxime resin was used as a source of palladium(0) in the chemoselective Heck reaction of acrolein diethyl acetal with aryl halides under ligand-free conditions. The use of typical Heck conditions afforded 3-arylpropionic esters, and the process can be directed to the synthesis of cinnamaldehydes under Cacchi conditions. These processes take place with rather low loading of the catalyst, which can be recovered by simple filtration and reused for at least five runs without competitive dehalogenation. This is the first time that a supported palladium complex has been reused under Cacchi conditions. ICP-OES analyses of the Pd content of the crude products in both transformations indicated lower leaching for the esters than for the aldehydes in the range up to 0.08 ppm for the esters and 0.8 ppm for the aldehydes. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Alacid, Emilio,Najera, Carmen
experimental part
p. 3102 - 3106
(2009/04/11)

C-C bond formation from alcohols and malonate half esters using borrowing hydrogen methodology
Alcohols have been used as alkylating agents in a decarboxylative reaction with malonate half esters via a borrowing hydrogen pathway catalysed by readily available Ru(PPh3)3Cl2.
Pridmore, Simon J.,Williams, Jonathan M.J.
scheme or table
p. 7413 - 7415
(2009/05/11)

Nickel-catalyzed 1,4-addition of trialkylboranes to α,β- unsaturated esters: Dramatic enhancement by addition of methanol
Equation presented Nickel catalyst systems for 1,4-addition of trialkylboranes to α,β-unsaturated esters have been developed. Addition of methanol was found to be essential for the alkylation reaction with 9-alkyl-9-BBNs.
Hirano, Koji,Yorimitsu, Hideki,Oshima, Koichiro
p. 1541 - 1544
(2008/02/02)

A novel one-pot conversion of amines to homologated esters in poly(ethylene glycol)
The first deaminative homologation of amines (-CH2NH2) to esters (-CH2CH2COOEt) in one-pot is reported. The reaction proceeds through, formation of an aldehyde from an amine in the presence of Pd/C as catalyst followed by Wittig reaction and catalytic hydrogenation using poly(ethylene glycol) as the solvent in one-pot.
Chandrasekhar,Pavan Kumar Reddy,Nagesh,Raji Reddy
p. 1269 - 1271
(2007/10/03)

Design, synthesis, and evaluation of potent, structurally novel peroxisome proliferator-activated receptor (PPAR) δ-selective agonists
A series of 3-(4-alkoxyphenyl)propanoic acid derivatives was prepared as candidate peroxisome proliferator-activated receptor (PPAR) δ-selective agonists, based on our previously discovered potent human PPARα/δ dual agonist TIPP-401 as a lead compound. Structure-activity relationship studies clearly indicated the importance of the chain length of the alkoxy group at the 4-position, and the n-butoxy compound exhibited the most potent PPARδ transactivation activity and highest PPARδ selectivity. The (S)-enantiomer of a representative compound exhibited extremely potent PPARδ transactivation activity, comparable with or somewhat superior to that of the known PPARδ-selective agonist, GW-501516. The representative compound regulated the expression of genes involved in lipid and glucose homeostasis, and should be useful not only as a chemical tool to study PPARδ function, but also as a candidate drug for the treatment of metabolic syndrome.
Kasuga, Jun-ichi,Nakagome, Izumi,Aoyama, Atsushi,Sako, Kumiko,Ishizawa, Michiyasu,Ogura, Michitaka,Makishima, Makoto,Hirono, Shuichi,Hashimoto, Yuichi,Miyachi, Hiroyuki
p. 5177 - 5190
(2008/03/14)

Facile synthesis of highly congested 1,2-diphosphinobenzenes from bis(phosphine)boronium salts
(Chemical Equation Presented) Bis(phosphine)boronium salts 3a-c were designed and prepared as key building blocks for the synthesis of highly congested diphosphinobenzenes. The preparation of sterically hindered ortho-phenylene-bridged diphosphines 1a-c was achieved by the reaction of the bis(phosphine)boronium salts 3a-c with difluorobenzenechromium complex 2 and subsequent removal of the BH2 group. The steric nature of diphosphine 1a was revealed in single-crystal X-ray analysis of its Rh complex.
Yamamoto, Yoshikazu,Koizumi, Toru,Katagiri, Kosuke,Furuya, Yui,Danjo, Hiroshi,Imamoto, Tsuneo,Yamaguchi, Kentaro
p. 6103 - 6106
(2007/10/03)

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.
Amatore, Muriel,Gosmini, Corinne,Perichon, Jacques
p. 6130 - 6134
(2007/10/03)

Poly(ethylene glycol) (400) as superior solvent medium against ionic liquids for catalytic hydrogenations with PtO2
Adams' catalyst in poly(ethylene glycol) (PEG) (400) has been found to be a superior solvent over the ionic liquids by severalfold in promoting the hydrogenation of various functional groups. Both the catalyst and PEG were recycled efficiently over 10 runs without loss of activity, and substrate cross contamination was not observed despite a change in the substrate four times.
Chandrasekhar, Srivari,Prakash, Samala Jaya,Rao, Chennamaneni Lohitha
p. 2196 - 2199
(2007/10/03)

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.
Kurono, Nobuhito,Inoue, Tomio,Tokuda, Masao
p. 11125 - 11131
(2007/10/03)

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.
Sohn, Stephanie S.,Bode, Jeffrey W.
p. 3873 - 3876
(2007/10/03)

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.
Nájera, Carmen,Botella, Luis
p. 9688 - 9695
(2007/10/03)

Process for preparing diltiazem using a heterogeneous trifunctional catalyst
The present invention comprises a simplified synthesis of (+)-diltiazem through IE-PdOsW wherein IE is ion-exchanger, catalyzed three-component coupling reaction and Fe3+-exchanged clay catalyzed ring opening of sulfite with 2-aminothiophenol followed by cyclization as key steps.
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(2008/06/13)

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.
Battistuzzi, Gianfranco,Cacchi, Sandro,Fabrizi, Giancarlo
p. 777 - 780
(2007/10/03)

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.
Battistuzzi, Gianfranco,Cacchi, Sandro,Fabrizi, Giancarlo,Bernini, Roberta
p. 1133 - 1136
(2007/10/03)

Ethyl 3-(p-cyanophenyl)propionate from ethyl 3-iodopropionate and p-cyanophenylzinc bromide [ benzenepropanoic acid, 4-cyano-, ethyl ester ]
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Jensen, Anne Eeg,Kneisel, Florian,Knochel, Paul,Girijavallabhan,Miller, Marvin J.
p. 35 - 35
(2017/09/29)

Electrochemical vinylation of aryl and vinyl halides with acrylate esters catalyzed by cobalt bromide
A consumable anode process permits the electrochemical Heck reaction between aromatic or vinylic halides and acrylate esters using cobalt bromide as catalyst associated with bipyridine as ligand in a mixture of acetonitrile/triethylamine/pyridine as solvent.
Gomes, Paulo,Gosmini, Corinne,Nédélec, Jean-Yves,Périchon, Jacques
p. 5901 - 5903
(2007/10/03)

Nickel-catalyzed electrochemical arylation of activated olefins
Nickel-catalyzed electrochemical conjugate additions of substituted aryl bromides to activated olefins under recently optimized reaction conditions are reported. Good to high yields were obtained, whatever the nature of substituents in the meta- and para-positions of the benzene ring. In the ortho-substituted series, yields were good with electron-donating substituents, but low with electron-withdrawing groups. The activation of aryl chlorides and the sequential functionalization of aryl dihalides were also investigated.
Condon, Sylvie,Dupre, Daniel,Falgayrac, Gilles,Nedelec, Jean-Yves
p. 105 - 111
(2007/10/03)

Synthesis of marine alkaloids isonaamine A, dorimidazole A, and preclathridine A. Iminophosphorane-mediated preparation of 2-amino-1,4- disubstituted imidazoles from α-azido esters
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Molina,Fresneda,Sanz
p. 2540 - 2544
(2007/10/03)

One-step cross-coupling reaction of functionalized alkyl iodides with aryl halides by the use of an electrochemical method
Organozinc compounds of functionalized alkyl iodide carrying an alkoxycarbonyl, cyano or alkenyl group were prepared in high yields under mild conditions (0°C-r.t., 10min in DMF) by the reaction of iodides with an electrogenerated reactive zinc (EGZn). Cross-coupling of the organozinc compounds with various aryl halides in the presence of 5 mol% Pd(P(o- Tol)3)2Cl2 in THF gave the corresponding cross-coupled products in moderate to high yields. These cross-coupling reactions can be also achieved in one step and in one pot by the use of an electrochemical method utilizing a Pt cathode and Zn anode.
Kurono, Nobuhito,Sugita, Kazuya,Takasugi, Shingo,Tokuda, Masao
p. 6097 - 6108
(2007/10/03)

Ni(II)-catalyzed cross-coupling between polyfunctional arylzinc derivatives and primary alkyl iodides [3]
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Giovannini,Knochel
p. 11186 - 11187
(2007/10/03)

Inhibition of uridine phosphorylase: Synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2- hydroxyethoxy)methyl]-5-benzyluracils
A series of 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils were synthesized and tested for inhibition of murine liver uridine phosphorylase (UrdPase). Inhibitors of UrdPase are reported to enhance the chemotherapeutic utility of 5-fluoro-2'-deoxyuridine and 5-fluorouracil and to ameliorate zidovudine- induced anemia in animal models. We prepared a series of 5-aryl-substituted analogues of 5-benzylacyclouridine (BAU), a good inhibitor of UrdPase (IC50 of 0.46 μM), to develop a compound with enhanced potency and improved pharmacokinetics. The first phase of structure-activity relationship studies on a series of 32 aryl-substituted 5-benzyluracils found several 5-(3- alkoxybenzyl) analogues of 5-benzyluracil with enhanced potency. The acyclovir side chain, the (2-hydroxyethoxy)methyl group, was substituted on the more potent aryl-substituted 5-benzyluracils. The two most potent compounds, 10y (3-propoxy) and 10dd (3-sec-butoxy), were inhibitors of UrdPase with IC50s of 0.047 and 0.027 μM, respectively. Six compounds were tested in vivo for effects on steady-state concentrations of circulating uridine in rats. Plasma uridine levels were elevated 3-9-fold by compound levels that ranged from 8 to 50 μM.
Orr,Musso,Boswell,Kelley,Joyner,Davis,Baccanari
p. 3850 - 3856
(2007/10/02)

REACTIONS OF ARYLAZO ARYL SULFONES WITH α,β-UNSATURATED ESTERS AND KETONES CATALYZED BY PALLADIUM(0) COMPLEX
The palladium(0) catalyzed reactions of arylazo aryl sulfones (1) with α,β-unsaturated esters in benzene give aryl-substituted esters as major products and hydroarylated esters as minor products.The reactions of 1 with acyclic α,β-unsaturated ketones give considerable amounts of hydroarylated ketones and aryl-substituted ketones under similar conditions, whereas the reactions of 1 with cyclic α,β-unsaturated ketones afforded selectively hydroarylated compounds and no formation of aryl-substituted ketones was found.A plausible reaction mechanism is proposed.Key words: Arylazo aryl sulfones; palladium(0) catalyst; arylation; α,β-unsaturated carbonyl compounds; diarylpalladiumII) intermediate; catalytic cycle.
Kamigata, Nobumasa,Satoh, Akira,Yoshida, Masato
p. 121 - 130
(2007/10/02)

Isocytosine H2-receptor histamine antagonists. I. Oxmetidine and related compounds
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Brown,Blakemore,Durant,Emmett,Ganellin,Parsons,Rawlings,Walker
p. 53 - 62
(2007/10/02)

SODIUM HYDROGEN TELLURIDE: A MECHANISTIC CHAMELEON
Relative rates of reduction of several α,β-unsaturated esters and styrenes added to recently obtained results from other substrates show that sodium hydrogen telluride (NaTeH) can react according to different mechanisms : nucleophilic substitution, hydride transfer, hydrogen atom transfer and electron transfer.
Barton, Derek H. R.,Bohe, Luis,Lusinchi, Xavier
p. 6609 - 6612
(2007/10/02)

A NOVEL METHOD FOR CARBON-CARBON BOND FORMATION PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYL FLUOROALKANESULFONATES WITH ORGANOZINC REAGENTS
Cross-coupling reaction of phenyl fluoroalkanesulfonates with three kinds of organozinc reagents in the presence of palladium gives the corresponding alkylbenzenes in good yields.A possible mechanism is suggested.
Chen, Qing-Yun,He, Ya-Bo
p. 2387 - 2388
(2007/10/02)

NICKEL CATALYZED COUPLING OF ACTIVATED ALKENES WITH ORGANIC HALIDES
Alkenenickel complexes catalyze the coupling of activated olefins with aryl or vinyl halides.Substitution or conjugate-addition products are obtained depending on the activating group in the alkene and on the nature of the organic halide.
Boldrini, G. P.,Savoia, D.,Tagliavini, E.,Trombini, C.,Ronchi, A. Umani
p. C62 - C64
(2007/10/02)

ARYLATION AND VINYLATION OF 2-CARBOETHOXYETHYLZINC IODIDE AND 3-CARBOETHOXYPROPYLZINC IODIDE CATALYZED BY PALLADIUM
By the palladium catalysis 2-carboethoxyethylzinc iodide reacts with aryl iodides and vinyl iodides or triflates to provide the coupling products (ethyl 3-arylpropionates and ethyl 4-pentenoates, respectively) in satisfactory yields.The similar coupling reaction is observed for the reaction with 3-carboethoxypropylzinc iodide.
Tamaru, Y.,Ochiai, H.,Nakamura, T.,Yoshida, Z.
p. 955 - 958
(2007/10/02)