- METHOD FOR PREPARING 1,3-DICARBONYL COMPOUND BASED ON METAL HYDRIDE/PALLADIUM COMPOUND SYSTEM
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Disclosed is a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method includes the following steps: suspending a palladium compound and a metal hydride in a solvent under the protection of nitrogen, t
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Paragraph 0041-0042
(2021/07/10)
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- APPLICATION OF METAL HYDRIDE/PALLADIUM COMPOUND SYSTEM IN PREPARATION OF 1,3-DICARBONYL COMPOUND IN CASCADE REACTION OF ELECTRON-DEFICIENT ALKENE COMPOUND
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Provided is an application of a metal hydride/palladium compound system in the preparation of a 1,3-dicarbonyl compound in a cascade reaction of an electron-deficient alkene compound, said reaction comprising the following steps: under the protection of n
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Paragraph 0041-0042
(2021/07/10)
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- Enantioenriched Quaternary α-Pentafluoroethyl Derivatives of Alkyl 1-Indanone-2-Carboxylates
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An electrophilic enantioselective catalytic method for the α-pentafluoroethylation of 3-oxoesters is described. Under the use of La(OTf)3 in combination with a (S,R)-indanyl-pybox ligand, good results in terms of yield and enantioselectivities were achieved (up to 89% ee). The reaction proceeds under mild conditions, leading to the formation of enantioenriched quaternary centers. This methodology uses an hypervalent iodine(III)-CF2CF3 reagent, and mechanistic investigations are consistent with the involvement of a radical pathway.
- Ballesteros, Anna,Granados, Albert,Vallribera, Adelina
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p. 10378 - 10387
(2020/09/23)
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- Pyrazoles: 'one-pot' synthesis from arenes and carboxylic acids
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A rapid and efficient method for 'one-pot' synthesis of pyrazoles from (hetero)arenes and carboxylic acids via successive formation of ketones and β-diketones followed by heterocyclization with hydrazine has been developed. The utility of the RCOOH/TfOH/TFAA acylation system for intermediate production of ketones and 1,3-diketones is a key feature of this approach. The preliminary evaluation of the anticancer activity of the synthesized pyrazoles is performed.
- Gong, Ming,Kim, Jung Keun,Kovalev, Vladimir V.,Kovaleva, Olga V.,Shokova, Elvira A.,Tafeenko, Viktor A.,Wu, Yangjie
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p. 5625 - 5638
(2020/08/21)
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- Redetermination of the Structure of a Water-Soluble Hypervalent Iodine(V) Reagent AIBX and Its Synthetic Utility in the Oxidation of Alcohols and Synthesis of Isoxazoline N-Oxides
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The structure of a water-soluble hypervalent iodine(V) reagent AIBX is re-examined through its single-crystal X-ray analysis and theoretical calculations including Mayer bond order and localized orbital locator (LOL) and AIBX is believed to be a pseudocyclic iodylarene because of the strong electron-withdrawing nature of the trimethylammonium cation on its phenyl ring, which would decrease the electron density of carboxylic anion and make the ortho-carboxyl oxygen anion incapable to form hypervalent bond with iodine atom. However, the cyclic benziodoxole structure of AIBX could be obtained by adding a Br?nsted acid, which was supported by the calculation result including the increase of Mayer bond order and the shortening of the I-O bond length. Moreover, the fact that the system of AIBX and TFA could oxidize various alcohols to their corresponding carbonyl compounds would indicate that AIBX constitutes a cyclic benziodoxole structure under acidic conditions. In addition, an efficient method has been developed for the synthesis of isoxazoline N-oxides via AIBX-induced dehydrogenative cyclization using β-keto esters as substrates and methyl nitroacetate as a nucleophile.
- Shen, Hui-Jie,Duan, Ya-Nan,Zheng, Ke,Zhang, Chi
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p. 14381 - 14393
(2019/11/13)
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- The Employment of Sodium Hydride as a Michael Donor in Palladium-catalyzed Reductions of α, β-Unsaturated Carbonyl Compounds
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Sodium hydride was employed as a Michael donor under the catalysis of PdCl2 for 1,4-conjugate reductions of α, β-unsaturated carbonyl compounds, which features operational simplicity, mild conditions and high atom-economy. The merits of NaH as a reductant were demonstrated by the one-pot or cascade reactions for the syntheses of complex molecules. (Figure presented.).
- Liu, Ye,Mao, Yujian,Hu, Yanwei,Gui, Jingjing,Wang, Liang,Wang, Wei,Zhang, Shilei
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supporting information
p. 1554 - 1558
(2019/02/16)
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- Method for preparing 1,3-dicarbonyl compound based on metal hydride/palladium compound system
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The invention discloses a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method comprises the following steps: making a palladium compound and metal hydride suspend in a solvent under the protection
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Paragraph 0028
(2019/01/08)
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- Application of metal hydride/ palladium compound system in preparing 1,3-dicarbonyl compound through cascade reaction in electron-deficient alkene compound
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The invention discloses application of a metal hydride/ palladium compound system in preparing a 1,3-dicarbonyl compound through cascade reaction in an electron-deficient alkene compound. The reactioncomprises the following steps of under the protection o
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Paragraph 0028
(2019/01/14)
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- Recyclable Hypervalent-Iodine-Mediated Dehydrogenative α,β′-Bifunctionalization of β-Keto Esters under Metal-Free Conditions
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We have developed a method for recyclable hypervalent-iodine-mediated direct dehydrogenative α,β′- bifunctionalization of β-ketoesters and β-diketones under metal-free conditions, which affords a straightforward way to synthesize benzo-fused 2,3-dihydrofurans. This efficient, mild method, which has a wide substrate scope and good functional-group tolerance, was used for the multistep synthesis of the protected aglycone of a naturally occurring phenolic glycoside. A mechanism involving Michael addition to an enone intermediate and subsequent oxidative cyclization is proposed.
- Duan, Ya-Nan,Cui, Li-Qian,Zuo, Lin-Hong,Zhang, Chi
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supporting information
p. 13052 - 13057
(2015/09/07)
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- Synthesis of indanones by sequential Heck-reduction-cyclization-alkylation (HRCA) reactions
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A simple and efficient synthesis of indanones, bearing a quaternary carbon centre, has been developed. The method features, in a one-pot process, the use of a multi-task palladium catalyst for the sequential Heck-reduction reactions, followed by a base-me
- Nassar-Hardy, Luma,Fabre, Sandy,Amer, Atef M.,Fouquet, Eric,Felpin, Franois-Xavier
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experimental part
p. 338 - 341
(2012/01/31)
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- Nickel-catalyzed electrochemical arylation of activated olefins
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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
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p. 105 - 111
(2007/10/03)
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- Selective synthesis of 1-indanones via tandem Knoevenagel condensation-cycloalkylation of β-dicarbonyl compounds and aldehydes
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Aromatic 1,3-dicarbonyl compounds react with not enolizable aldehydes in the presence of C2H5MgBr or AlCl3 affording 2-carbethoxy- and 2-acetyl-1-indanones via tandem, Knoevenagel condensation-cycloalkylation process.
- Sartori, Giovanni,Maggi, Raimondo,Bigi, Franca,Porta, Cecilia,Tao, Xiaochun,Bernardi, Gian Luca,Ianelli, Sandra,Nardelli, Mario
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p. 12179 - 12192
(2007/10/02)
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- Friedel-Crafts Coordinated Processes: 1-Oxoindanes from Aromatic β-Dicarbonyl Compounds and Aldehydes
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Variously substituted 1-oxoindanes were synthesized by highly selective bis-alkylation of aromatic β-dicarbonyl compounds with non enolizable aldehydes. - Key words: 1-Oxoindanes; β-dicarbonyl chelates; vicinal bis-alkylation.
- Sartori, Giovanni,Bigi, Franca,Maggi, Raimondo,Bernardi, Gian Luca
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p. 7339 - 7342
(2007/10/02)
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- FRIEDEL-CRAFTS COORDINATED PROCESSES: HIGHLY SELECTIVE SYNTHESIS OF ETHYL 1-OXO-2-INDANCARBOXYLATES AND 1-OXO-2-ACETYLINDANES
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Alkyl 1-oxo-2-indancarboxylates and 1-oxo-2-acetylindanes were synthesized in good yields by methylenation of aromatic β-dicarbonyl compounds with MeOCH2COCl-AlCl3 reagent. Key words: 1-oxo-indanes, chloromethylation, methoxymethylation.
- Sartori, Giovanni,Bigi, Franca,Tao, Xiaochun,Casnati, Giuseppe,Canali, Giacomo
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p. 4771 - 4774
(2007/10/02)
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- Photolysis of cyclic enol esters in the presence or absence of a single electron transfer photosensitizer
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The photochemistry of enol esters 1 is dominated by electrocyclic ring opening (1b → 3+4), 1,3-acyl migration (1c,d → 6c,d) and [2 + 2] dimerization (1d → 11). Photosensitization with triphenylpyrylium tetrafluoroborate (TPT) enhances formation of oxidation products (1b → 5,1c,d → 9c,d + 10c,d), presumably through the intermediacy of radical cations 1b-d+.
- Climent,Garcia,Iborra,Miranda,Primo
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p. 9289 - 9296
(2007/10/02)
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