- IBX-TfOH mediated oxidation of alcohols to aldehydes and ketones under mild reaction conditions
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An efficient, practical and facile procedure has been developed for the oxidation of primary and secondary alcohols using IBX-TfOH catalytic system in 1,4-dioxane at ambient temperature. The reaction affords quantitative yields of the corresponding carbonyl compounds without the formation of over oxidized products. The present synthetic protocol is compatible with a variety of substrates having arene, heteroarene and alkene functionalities. The developed synthetic protocol can be used for higher scale reactions as evident by the oxidation of alcohol at 1 g scale in higher yields by a simple filtration process.
- Kumar, Kamlesh,Kumar, Prashant,Joshi, Penny,Rawat, Diwan S
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Read Online
- Pd-nanoparticles stabilized by pyridine-functionalized poly(ethylene glycol) as catalyst for the aerobic oxidation of α,β-unsaturated alcohols in water
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The synthesis and coordination chemistry of 4-pyridinemethylene end-capped MeO-PEG (LPy) to Pd(II) was investigated. The PEG-based macroligand LPy was straightforwardly synthesized by pyridine end-functionalization of PEG monomethyl ether and employed to stabilize Pd(II) in a neutral (1a) and bis-cationic (2a) macrocomplex, characterized by a LPy to Pd molar ratio of 2 and 4, respectively. The homogeneous distribution of the Pd-NPs in 2b exerted a significant stabilizing effect on the poly(ether) chain of LPy against its oxidative thermal degradation. From a screening of the Pd(II)- and Pd-NP-based catalysts in the aerobic oxidation of unsaturated alcohols in water emerged 2b as the most stable catalyst, showing TOF-values up to 200-h and high chemoselectivity even for prolonged reaction times.
- Giachi, Guido,Oberhauser, Werner,Frediani, Marco,Passaglia, Elisa,Capozzoli, Laura,Rosi, Luca
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Read Online
- Design and synthesis of chitin synthase inhibitors as potent fungicides
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Chitin is a structural component of fungal cell walls but is absent in vertebrates, mammals, and humans. Chitin synthase is thus an attractive molecular target for developing fungicides. Based on the structure of its donor substrate, UDP-N-acetyl-glucosamine, as well as the modelled structure of the bacterial chitin synthase NodC, we designed a novel scaffold which was then further optimized into a series of chitin synthase inhibitors. The most potent inhibitor, compound 13, exhibited high chitin synthase inhibitory activity with an IC50 value of 64.5?μmol/L. All of the inhibitors exhibited antifungal activities against the growth of agriculturally-destructive fungi, Fusarium graminearum, Botrytis cinerea, and Colletotrichum lagenarium. This work presents a new scaffold which can be used for the development of novel fungicides.
- Chen, Qi,Zhang, Ji-Wei,Chen, Lu-Lu,Yang, Jun,Yang, Xin-Ling,Ling, Yun,Yang, Qing
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Read Online
- Reaction-driven surface restructuring and selectivity control in allylic alcohol catalytic aerobic oxidation over Pd
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Synchronous, time-resolved DRIFTS/MS/XAS cycling studies of the vapor-phase selective aerobic oxidation of crotyl alcohol over nanoparticulate Pd have revealed surface oxide as the desired catalytically active phase, with dynamic, reaction-induced Pd redox processes controlling selective versus combustion pathways.
- Lee, Adam F.,Ellis, Christine V.,Naughton, James N.,Newton, Mark A.,Parlett, Christopher M. A.,Wilson, Karen
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Read Online
- Method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde
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The invention discloses a method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde. The method comprises the following steps: 1) under the catalysis of alkali liquor, enabling phenylpropionaldehyde and an aqueous formaldehyde solution to pass through a continuous tank reactor, and conducting condensing to obtain a 2-benzylacrolein intermediate; and 2) carrying out hydroisomerization to obtain alpha-methylcinnamaldehyde. The raw materials, namely phenylpropionaldehyde and formaldehyde selected in the method are widely and readily available and low in price, so the method has a cost advantage; and the formaldehyde has good water solubility, the phenylpropionaldehyde is not easy to undergo the Cannizaro side reaction, and the intermediate prepared by condensation of the phenylpropionaldehyde and the phenylpropionaldehyde is easy to realize high yield.
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Paragraph 0011; 0051-0059
(2021/03/31)
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- Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
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We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
- Aleku, Godwin A.,Leys, David,Roberts, George W.
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p. 3927 - 3939
(2020/07/09)
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- Pd-Catalyzed Carbonylation of Vinyl Triflates to Afford α,β-Unsaturated Aldehydes, Esters, and Amides under Mild Conditions
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An efficient and general protocol for the synthesis of α,β-unsaturated aldehydes, esters, and amides via carbonylation of vinyl triflates including derivatives of camphor, ketoisophorone, verbenone, and pulegone was developed. Crucial for these transformations is the use of a specific palladium catalyst containing a pyridyl-substituted dtbpx-type ligand. This procedure also allows for an easy access of dicarbonylated products from the corresponding ketones.
- Zhang, Shaoke,Neumann, Helfried,Beller, Matthias
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p. 3528 - 3532
(2019/05/24)
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- CO2-Catalyzed oxidation of benzylic and allylic alcohols with DMSO
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CO2-catalyzed transition-metal-free oxidation of alcohols has been achieved. Earlier, several methodologies have been explored for alcohol oxidations based on transition-metal catalysts. However, owing to the cheaper price, easy separation and nontoxicity, transition-metal-free systems are in high demand to the pharmaceutical industries. For this reason, various primary and secondary alcohols have been selectively oxidized to the corresponding carbonyl compounds using CO2 as a catalyst in the presence of different functional groups such as nitrile, nitro, aldehyde, ester, halogen, ether, and so on. At the end, transition-metal-free syntheses of pharmaceuticals have also been achieved. Finally, the role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments and DFT calculations.
- Riemer, Daniel,Mandaviya, Bhavdip,Schilling, Waldemar,G?tz, Anne Charlotte,Kühl, Torben,Finger, Markus,Das, Shoubhik
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p. 3030 - 3034
(2018/04/14)
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- Fe(NO3)3/2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ): An efficient catalyst system for selective oxidation of alcohols under aerobic conditions
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A practical and efficient catalyst system for the oxidation of alcohols to carbonyl compounds using catalytic amounts of DDQ and Fe(NO3)3 with air as the environmentally benign oxidant has been developed. A variety of benzylic, heterocyclic, allylic and propargylic alcohols were smoothly converted into aldehydes or ketones in good to excellent yields. In case of large-scale reaction for the oxidation of benzyl alcohol, benzaldehyde was obtained in 93% isolated yield. Moreover, a possible reaction mechanism was proposed.
- Hu, Yongke,Chen, Lei,Li, Bindong
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- A synthetic route to 4-alkyl-α-methylhydrocinnamylaldehydes
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The 4-Alkyl-α-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-α-methylcinnamylaldehydes preparation with similar results. In the second step—hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.
- Vrbková, Eva,Vysko?ilová, Eli?ka,Rott, Martin,Zapletal, Martin,?erveny, Libor
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p. 2603 - 2613
(2017/03/22)
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- Engineering a Promiscuous Tautomerase into a More Efficient Aldolase for Self-Condensations of Linear Aliphatic Aldehydes
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The enzyme 4-oxalocrotonate tautomerase (4-OT) from Pseudomonas putida mt-2 takes part in a catabolic pathway for aromatic hydrocarbons, where it catalyzes the conversion of 2hydroxyhexa-2,4-dienedioate into 2-oxohexa-3-enedioate. This tautomerase can also promiscuously catalyze carbon–carbon bond-forming reactions, including various types of aldol reactions, by using its amino-terminal proline as a key catalytic residue. Here, we used systematic mutagenesis to identify two hotspots in 4-OT (Met45 and Phe50) at which single mutations give marked improvements in aldolase activity for the self-condensation of propanal. Activity screening of a focused library in which these two hotspots were varied led to the discovery of a 4-OT variant (M45Y/F50V) with strongly enhanced aldolase activity in the self-condensation of linear aliphatic aldehydes, such as acetaldehyde, propanal, and butanal, to yield α,β-unsaturated aldehydes. With both propanal and benzaldehyde, this double mutant, unlike the previously constructed single mutant F50A, mainly catalyzes the self-condensation of propanal rather than the cross-condensation of propanal and benzaldehyde, thus indicating that it indeed has altered substrate specificity. This variant could serve as a template to create new biocatalysts that lack dehydration activity and possess further enhanced aldolase activity, thus enabling the efficient enzymatic self-coupling of aliphatic aldehydes.
- Rahimi, Mehran,van der Meer, Jan-Ytzen,Geertsema, Edzard M.,Poelarends, Gerrit J.
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p. 1435 - 1441
(2017/07/25)
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- Bifunctional organocatalysts for the synthesis of jasminaldehyde and their derivatives
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L-Proline in the presence of benzoic acid is found to be an effective catalytic system for the cross-aldol condensation of benzaldehyde with 1-heptanal under solvent free condition amongst the several amino acids screened for this reaction. Under the optimized reaction conditions, the desired product (e.g. jasminaldehyde) is formed up to 96% selectivity in one hour using the desired arylaldehyde: 1-alkanaldehyde ratio as low as 2:1 under controlled addition of 1-alkanaldehyde.
- Ganga, Venkata Subba Rao,Abdi, Sayed H.R.,Kureshy, Rukhsana I.,Khan, Noor-Ul H.,Bajaj, Hari C.
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p. 950 - 955
(2017/08/04)
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- The bioinspired design of a reagent allows the functionalization of Cα-H of α,β-unsaturated carbonyl compounds via the Baylis-Hillman chemistry under ambient conditions
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A rationally designed reagent capable of affecting alkylation at Cα of α,β-unsaturated carbonyl compounds is reported. The reaction proceeded at room temperature without any additives. The pH and H-bond formation during the reaction play a key role in the working of the reagent.
- Singh, Palwinder,Kumar, Arun,Kaur, Sukhmeet,Kaur, Jagroop,Singh, Harpreet
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supporting information
p. 2936 - 2939
(2016/02/20)
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- Oxidative Cleavage of Silyl Ethers by an Oxoammonium Salt
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A method for the oxidative cleavage of silyl ethers to their corresponding carbonyl species mediated by an oxoammonium salt is described. The resulting aldehydes and ketones are obtained under mild reaction conditions with no observed overoxidation. For robust substrates, heating to reflux temperatures significantly reduces the reaction time.
- Loman, Jacob J.,Pistritto, Vincent A.,Kelly, Christopher B.,Leadbeater, Nicholas E.
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p. 2372 - 2377
(2016/09/28)
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- Catalytic C-H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand
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The direct arylation of aliphatic aldehydes has been established via Pd-catalyzed sp3 C-H bond functionalization in the presence of 3-aminopropanoic acids as transient directing groups. The reaction showed excellent functional group compatibility and chemoselectivity in which a predominant preference for functionalizing unactivated β-C-H bonds of methyl groups over others was achieved. In addition, C-H bonds of unactivated secondary sp3 carbons can also be functionalized. The extreme popularity and importance of aliphatic aldehydes would result in broad applications of this novel method in organic chemistry and medicinal sciences.
- Yang, Ke,Li, Qun,Liu, Yongbing,Li, Guigen,Ge, Haibo
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supporting information
p. 12775 - 12778
(2016/10/13)
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- Highly regio- And enantioselective synthesis of g,d-unsaturated amido esters by catalytic hydrogenation of conjugated enamides
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An efficient and highly regio- and enantioselective catalytic asymmetric hydrogenation of a,γ-dienamido esters to g,d-unsaturated amido esters has been achieved using Rh/ TangPhos as the catalyst. A series of γ,δ-unsaturated amido acids were furnished in excellent yields with up to 99%ee. This effective methodology was applied in the asymmetric synthesis of key intermediate of Ramipril, an ACE inhibitor.
- Min, Gao,Jing-jing, Meng,Hui, Lv,Xumu, Zhang
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supporting information
p. 1885 - 1887
(2015/02/19)
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- METHOD FOR PRODUCING α,β-UNSATURATED CARBONYL COMPOUNDS
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PROBLEM TO BE SOLVED: To provide a simple and efficient, novel method for producing α,β-unsaturated carbonyl compounds, which can provide α,β-unsaturated carbonyl compounds from allyl alcohols with high yields under a mild reaction condition, and has extremely little influence and toxicity on the environment and the human body. SOLUTION: Provided is a method for producing α,β-unsaturated carbonyl compounds, the method comprising reacting allyl alcohols and hydrogen peroxide to carbonylate alcohol portions to produce corresponding α,β-unsaturated carbonyl compounds. As a reaction catalyst, there are used an Fe(II) or Fe(III) salt soluble in water or an organic solvent, and at least one picolinic acid selected from 2-picolinic acid and 6-C1-4 alkyl-2-picolinic acid in coexistence in a ratio of 1:1 to 1:4. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0037; 0042-0043
(2016/12/26)
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- Trio catalysis merging enamine, br?nsted acid, and metal lewis acid catalysis: Asymmetric three-component aza-diels-alder reaction of substituted cinnamaldehydes, cyclic ketones, and arylamines
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A trio catalyst system, composed of arylamine, BINOL-derived phosphoric acid, and Y(OTf)3, enables the combination of enamine catalysis with both hard metal Lewis acid catalysis and Br?nsted acid catalysis for the first time. Using this catalyst system, a three-component aza-Diels-Alder reaction of substituted cinnamaldehyde, cyclic ketone, and arylamine is carried out with high chemo- and enantioselectivity, affording a series of optically active 1,4-dihydropyridine (DHP) derivatives are obtained in 91-99 % ee and 59-84 % yield. DHPs bearing a chiral quaternary carbon center are also obtained with good enantioselectivity and moderate yield (three examples). Preliminary mechanistic investigations have also been conducted.
- Deng, Yongming,Kumar, Siddhartha,Wheeler, Kraig,Wang, Hong
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p. 7874 - 7880
(2015/05/20)
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- Synthesis, spectral, electrochemical and catalytic properties of Ru(III) Schiff base complexes containing N, O donors
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A series of new hexa coordinated ruthenium(III) complexes of the type [RuY2(EPh3)2(X-DPMP)] (where Y = Br or Cl; E = P or As; DPMP = 2-[(2,6-Diisopropyl-phenylimino)-methyl]-phenol, X = H, Br, Cl, I and Ph) have been synthesized by equimolar [RuY3(EPh 3)3] and the Schiff base ligands in benzene. The bidentate Schiff base ligands (X-DPMP) have been derived from condensation of 2,6-diisopropylaniline with mono and multisubstituted salicylaldehyde derivatives. The complexes have been characterized by elemental analysis, magnetic susceptibility, UV-Vis., IR and EPR spectral and electrochemical measurements. All the ruthenium(III) complexes are found to be stable, paramagnetic, low spin, redox active and display either quasi reversible or irreversible redox couples based on metal centre. They have exhibited catalytic activity for the oxidation of wide range of primary and secondary alcohols to corresponding aldehydes or ketones with moderate to high conversion in the presence of N-methylmorpholine-N-oxide (NMO) as co-oxidant.
- Raja, K. Kanmani,Indra Gandhi,Lekha,Easwaramoorthy,Rajagopal
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- CuI/N4 ligand/TEMPO derivatives: A mild and highly efficient system for aerobic oxidation of primary alcohols
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A new system consisting of a copper(I) complex generated in situ from a tetradentate nitrogen ligand and CuI in combination with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) derivatives was successfully developed. The system was suitable for efficient and selective aerobic oxidation of primary benzyl and allyl alcohols with a wide range of functional groups to the corresponding aldehydes at room temperature. The best result was obtained with N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine as the ligand and 4-OH-TEMPO as a cocatalyst in CH3CN. In addition, high-resolution mass spectrometry, ultraviolet-visible spectroscopy, and electrochemical experiments were used to provide evidence of intermediates.
- Zhang, Shufang,Miao, Chengxia,Xu, Daqian,Sun, Wei,Xia, Chungu
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p. 1864 - 1873
(2015/09/28)
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- Chemoselective hydrogen peroxide oxidation of allylic and benzylic alcohols under mild reaction conditions catalyzed by simple iron-picolinate complexes
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Chemoselective oxidation of allylic alcohols to α,β-unsaturated carbonyl compounds proceeded efficiently using hydrogen peroxide with iron-picolinate catalysts. The in situ generated [Fe(Me-Pic)3] (Me-Pic = 6-methylpicolinate) catalyzed oxidation of the alcohol moiety of primary allylic alcohols while the [Fe(Pic)3] (Pic = picolinate) and [Fe(Me-Pic)2(Pic)] did not show sufficient catalytic activity. the Partner Organisations 2014.
- Tanaka, Shinji,Kon, Yoshihiro,Nakashima, Takuya,Sato, Kazuhiko
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p. 37674 - 37678
(2014/11/07)
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- Chemoselective hydrogen peroxide oxidation of allylic and benzylic alcohols under mild reaction conditions catalyzed by simple iron-picolinate complexes
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Chemoselective oxidation of allylic alcohols to α,β-unsaturated carbonyl compounds proceeded efficiently using hydrogen peroxide with iron-picolinate catalysts. The in situ generated [Fe(Me-Pic)3] (Me-Pic = 6-methylpicolinate) catalyzed oxidation of the alcohol moiety of primary allylic alcohols while the [Fe(Pic)3] (Pic = picolinate) and [Fe(Me-Pic)2(Pic)] did not show sufficient catalytic activity. This journal is
- Tanaka, Shinji,Kon, Yoshihiro,Nakashima, Takuya,Sato, Kazuhiko
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p. 37674 - 37678
(2014/12/11)
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- Secondary amine catalyzed retro-aldol reactions of enals and enones: One-pot conversion of enals to α-substituted derivatives
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A practical synthetic procedure to hydrolytically cleave the C,C-double bond of α,β-unsaturated aldehydes and ketones has been developed. Secondary amines are employed as organocatalysts for the retro-aldol process under simple and mild reaction conditions. Beside the generation of the parent aromatic aldehydes, the synthetic procedure has been successfully used in a one-pot reaction sequence to convert simple cinnamaldehydes into their α-aryl/alkyl substituted derivatives.
- Enders, Dieter,Nguyen, Thanh V.
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experimental part
p. 2091 - 2095
(2012/07/14)
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- 2-METHYLENE-5-SUBSTITUTED-METHYLENECYCLOPENTANONE DERIVATIVES AND USE THEREOF
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The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.
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Page/Page column 13
(2011/04/18)
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- Gold-catalysed activation of epoxides: Application in the synthesis of bicyclic ketals
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Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with Ca≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation experiments were carried out to ascertain the mechanism of the reaction. Sequential activation of epoxide and alkyne moieties by a gold catalyst in acetone as solvent has been achieved. This strategyhas been employed to synthesise bicyclic ketals from epoxy alkynes. Copyright
- Balamurugan, Rengarajan,Kothapalli, Raveendra Babu,Thota, Ganesh Kumar
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supporting information; scheme or table
p. 1557 - 1569
(2011/04/25)
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- 2-METHYLENE-5-SUBSTITUTED METHYLENE CYCLOPENTANONE DERIVATIVES AND USE THEREOF
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The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.
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Page/Page column 18
(2010/11/19)
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- Highly enantioselective bioreduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae
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Biocatalytic reduction of 2-fluorocinnamyl alcohols mediated by Saccharomyces cerevisiae was investigated in phosphate buffer solutions. Product analysis clearly showed that (S)-2-fluoro-3-arylpropanols were afforded in high yields with up to 92% ee value.
- Luo, Fan,Wang, Ping,Gong, Yuefa
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supporting information; experimental part
p. 1693 - 1695
(2010/04/29)
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- ANALGESIC 5, 9 - METHANOCYCLOOCTA (b) PYRIDIN - 2 (1H) - ONE DERIVATIVES, THEIR PREPARATION METHOD AND USE
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Compounds represented by the Formula I or salts, hydrates thereof, wherein R1, R8, R11 and R12 are H or C1-4 hydrocarbonyl respectively; R2, R3, R6 and R7 are H, halogen or C1-4 hydrocarbonyl respectively; R4 is C1-6 hydrocarbonyl or Ar; or =CR4R3 is cyclopentylidene, cyclohexylidene, 1-methylpiperidyl-4-idene or indenyl-1-idene; R5 is H, 1-4 same or different F, Cl, Br, CF3, R9, OR9, NR9R10, NO2, CN, COOR9, O2CR9, CONR9R10, NR9C(O)R10, heterocyclic, aryl or groups represented by the Formula II respectively; R9 and R10 are H or C1-6 hydrocarbonyl; Ar is aromatic ring; m is 0, 1 or 2; n is 0, 1, 2, 3 or 4, for treating mammal pain, functional painful syndrome, organic painful syndrome or tissue painful syndrome, and their preparation method.
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Page/Page column 15
(2009/04/23)
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- A RhCl(PPh3)3/BF3·OEt2 co-promoted direct C-C cross-coupling of alcohols at β-position with aldehydes
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A novel RhCl(PPh3)3/BF3·OEt2 co-promoted direct C-C cross-coupling of primary and secondary alcohols at β-position with aldehyde was developed. This reaction could provide an efficient synthesis of a series of α
- Zhang, Shu-Yu,Tu, Yong-Qiang,Fan, Chun-An,Yang, Ming,Zhang, Fu-Min
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body text
p. 4178 - 4181
(2009/12/01)
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- Aerobic photocatalytic oxidation of activated benzylic and allylic alcohols to carbonyl compounds catalyzed by molecular iodine
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An efficient, selective and environmentally benign photocatalytic system in acetonitrile has been developed for aerobic oxidation of activated benzylic and allylic alcohols into their corresponding aldehydes and ketones without the need for a transition metal in moderate to excellent yields with a catalytic amount of iodine. Very high inter- and intramolecular chemoselectivities are observed when benzylic OH groups are oxidized in the presence of aliphatic (nonbenzylic) hydroxyls.
- Farhadi, Saeid,Zabardasti, Abedien,Babazadeh, Zaynab
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p. 8953 - 8957
(2007/10/03)
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- Highly selective oxidation of allylic alcohols catalysed by monodispersed 8-shell Pd nanoclusters in the presence of molecular oxygen
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Treatment of Pd4phen2(CO)2(OAc)4 with metal nitrates such as Cu(NO3)2 produced monodispersed Pd nanoclusters with a mean diameter and standard deviation (d±σ) of 38±2.1 A (σ/d = 6%). The Pd nanoclusters act as heterogeneous catalysts for the selective oxidation of primary aromatic allylic alcohols using molecular oxygen as an oxidant. This unique catalysis can be ascribed to multiple interactions between the alcohol and specific ensemble sites consisting of Pd0, Pd+, and Pd2+ on the cluster surface.
- Choi, Kwang-Min,Akita, Tomoki,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
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p. 324 - 328
(2007/10/03)
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- Synthesis and application of 2,6-dicarboxypyridinium chlorochromate as a new oxidizing reagent for alcohols, silyl ethers, and THP ethers under mild and non-aqueous conditions
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2,6-Dicarboxypyridinium chlorochromate can be used as a rapid, mild and efficient reagent for oxidation of alcohols, silyl ethers and THP ethers to their carbonyl compounds.
- Tajbakhsh, Mahmood,Hosseinzadeh, Rahman,Niaki, Mohammad Yazdani
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p. 508 - 510
(2007/10/03)
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- Silylamines in Organic Synthesis. Reactivity of N,N-Bis(silyl) Enamines toward Electrophiles. A Route to Substituted 2-Aza-1,3-butadienes and Pyridines
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N,N-Bis(silyl) enamines appeared to be weak nucleophilic reagents and exhibited a very low reactivity toward electrophiles.However, in the presence of a nucleophilic catalyst, nucleophilic activation of the silicon-nitrogen bond was observed.Under fluoride ion catalysis (TBAF or CsF), N,N-bis(silyl) enamines reacted with carbonyl compounds to give substituted 2-aza-1,3-butadienes.Good yields were obtained in reactions with aromatic aldehydes or ketones.In the case of aliphatic carbonyl compounds, 2-aza 1,3-dienes were only formed in moderate yields.Interestingly, enamidines were easily obtained in high yields upon reactions of dimethylformamide in the presence of MeONa as catalyst.The reaction of aromatic α,β-unsaturated ketones gave 2-aza 1,3,5-trienes, which were not isolated but underwent an intramolecular cycloaddition reaction with regioselective formation of substituted 2,4-diarylpyridines.
- Corriu, Robert J. P.,Moreau, Joel J. E.,Pataud-Sat, Magali
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p. 2878 - 2884
(2007/10/02)
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- ETHERS D'ENOLS β-LITHIES; SYNTHESES D'ALDEHYDES α-ETHYLENIQUES
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β-Bromoenol ethers readily undergo bromine-lithium exchange with t-butyllithium in ether or THF at -70 deg C.The resulting lithium products react with aldehydes and ketones to produce, after hydrolysis, β-hydroxyenol ethers (basic medium) or α-unsaturated aldehydes (acidic medium).
- Duhamel, Lucette,Tombret, Francis,Mollier, Yves
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