- Visible-Light Decatungstate/Disulfide Dual Catalysis for the Hydro-Functionalization of Styrenes
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We describe an efficient photoredox system, relying on decatungstate/disulfide catalysts, for the hydrofunctionalization of styrenes. In this methodology the use of disulfide as a cocatalyst was shown to be crucial for the reaction efficiency. This photoredox system was employed for the hydro-carbamoylation, -acylation, -alkylation, and -silylation of styrenes, giving access to a large variety of useful building blocks and high-value molecules such as amides and unsymmetrical ketones from simple starting materials.
- Prieto, Alexis,Taillefer, Marc
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supporting information
p. 1484 - 1488
(2021/03/08)
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- Primary fatty acid amide preparation method
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The present invention provides a primary fatty acid amide preparation method. According to the present invention, under the action of a single auxiliary agent phosphine-containing transition metal catalyst or a combined auxiliary agent comprising a phosphine-free transition metal catalyst and a phosphine-containing ligand, terminally substituted olefin or cyclo-olefin, carbon monoxide and an ammonium salt are subjected to a hydrogen carboamidation reaction so as to prepare the primary fatty acid amide compound in one step; the raw material and the catalyst of the reaction are inexpensive and easy to obtain, and the synthesis process is simple, such that the synthesis cost is substantially reduced; the preparation method has characteristics of mild reaction condition and high yield, and issuitable for industrial production; and the raw material and the catalyst of the reaction are clean, non-toxic and low environment pollution.
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Paragraph 0213-0215
(2018/10/19)
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- Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride
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Palladium-catalyzed hydroaminocarbonylation of alkenes for the synthesis of primary amides has long been an elusive aim. Here, we report an efficient catalytic system which enables inexpensive NH4Cl to be utilized as a practical alternative to gaseous ammonia for the palladium-catalyzed alkene-hydroaminocarbonylation reaction. Through appropriate choice of the palladium precursors and ligands, either branched or linear primary amides can be obtained in good yields with good to excellent regioselectivities. Primary mechanistic studies were conducted and disclosed that electrophilic acylpalladium species were capable of capturing the NH2-moiety from ammonium salts to form amides in the presence of CO with NMP as a base.
- Gao, Bao,Zhang, Guoying,Zhou, Xibing,Huang, Hanmin
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p. 380 - 386
(2018/01/12)
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- NEW TRPA1 ANTAGONISTS
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The present invention relates to compounds of Formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by TRPA1 channel inhibition or antagonism.
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Page/Page column 79; 80
(2017/08/01)
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- A Unique Mdm2-Binding Mode of the 3-Pyrrolin-2-one- and 2-Furanone-Based Antagonists of the p53-Mdm2 Interaction
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The p53 pathway is inactivated in almost all types of cancer by mutations in the p53 encoding gene or overexpression of the p53 negative regulators, Mdm2 and/or Mdmx. Restoration of the p53 function by inhibition of the p53-Mdm2/Mdmx interaction opens up
- Surmiak, Ewa,Twarda-Clapa, Aleksandra,Zak, Krzysztof M.,Musielak, Bogdan,Tomala, Marcin D.,Kubica, Katarzyna,Grudnik, Przemyslaw,Madej, Mariusz,Jablonski, Mateusz,Potempa, Jan,Kalinowska-Tluscik, Justyna,D?mling, Alexander,Dubin, Grzegorz,Holak, Tad A.
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p. 3310 - 3318
(2016/12/23)
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- Novel palladium-on-carbon/diphenyl sulfide complex for chemoselective hydrogenation: Preparation, characterization, and application
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A diphenyl sulfide immobilized on palladium-on-carbon system, Pd/C[Ph 2S], was developed to achieve the highly chemoselective hydrogenation of alkenes, acetylenes, azides, and nitro groups in the presence of aromatic ketones, halides, benzyl esters, and N-Cbz protective groups. Instrumental analyses of the heterogeneous catalyst demonstrated that diphenylsul fide was embedded on Pd/C via coordination of its sulfur atom to palladium metal or physical interaction with graphite layers of the activated carbon. The catalyst could be recovered and reused at least five times without any significant loss of the reactivity.
- Mori, Akinori,Mizusaki, Tomoteru,Kawase, Masami,Maegawa, Tomohiro,Monguchi, Yasunari,Takao, Shinobu,Takagi, Yukio,Sajikia, Hironao
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experimental part
p. 406 - 410
(2009/04/06)
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- Aromatic chlorination of ω-phenylalkylamines and ω- phenylalkylamides in carbon tetrachloride and α,α,α- trifluorotoluene
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The aromatic halogenation of simple alkylbenzenes with chlorine proceeds smoothly in acetic acid but is much less efficient in less polar solvents. By contrast chlorination of ω-phenylalkylamines, such as 3-phenylpropylamine, occurs readily in either acetic acid, carbon tetrachloride or α,α,α-trifluorotoluene, and in the latter solvents gives high proportions of ortho-chlorinated products. These effects are attributable to the involvement of N-chloroamines as reaction intermediates, with intramolecular delivery of the chlorine electrophile. ω-Phenylalkylamides, such as 3-phenylpropionamide, also easily undergo aromatic chlorination in carbon tetrachloride and α,α,α-trifluorotoluene. These reactions generally show a first-order dependence on the substrate concentration, but not on the amount of chlorine. With carbon tetrachloride, very similar reaction rates are observed with chlorine concentrations ranging from 0.1-1.5 M. In α,α,α-trifluorotoluene, the rates reach a plateau at a chlorine concentration of approximately 0.2 M. These features indicate that the reactions proceed via the formation of intermediates which evidence suggests may be the corresponding O-chloroimidates. Irrespective of the mechanistic details, the reactions are remarkably rapid, being faster than analogous reactions in acetic acid and three to four orders of magnitude more rapid than reactions of simple alkylbenzenes in carbon tetrachloride. Therefore, chlorination of the amines and amides may be accomplished without the need for highly polar solvents, added catalysts or large excesses of chlorine, which are often employed for electrophilic aromatic substitutions. Although the use of carbon tetrachloride is becoming increasingly impractical due to environmental concerns, the trifluorotoluene is a suitable alternative. The Royal Society of Chemistry 2006.
- O'Connell, Jenny L.,Simpson, Jamie S.,Dumanski, Paul G.,Simpson, Gregory W.,Easton, Christopher J.
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p. 2716 - 2723
(2008/02/08)
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- Pd/C-catalyzed chemoselective hydrogenation in the presence of diphenylsulfide
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A Pd/C-catalyzed chemoselective hydrogenation using diphenylsulfide as a catalyst poison has been developed. This methodology selectively hydrogenates olefin and acetylene functionalities without hydrogenolysis of aromatic carbonyls and halogens, benzyl esters, and N-Cbz protective groups.
- Mori, Akinori,Miyakawa, Yumi,Ohashi, Eri,Haga, Tomoko,Maegawa, Tomohiro,Sajiki, Hironao
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p. 3279 - 3281
(2007/10/03)
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- Chemoselective hydrogenation method catalyzed by Pd/C using diphenylsulfide as a reasonable catalyst poison
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While Pd/C is one of the most useful catalysts for hydrogenation, the high catalyst activity of Pd/C causes difficulty in its application to chemoselective hydrogenation between different types of reducible functionalities. In order to achieve chemoselective hydrogenation using Pd/C, we investigated catalyst poison as a controller of the catalyst activity. We found that the addition of Ph2S (diphenylsulfide) to the Pd/C-catalyzed hydrogenation reaction mixture led to reasonable deactivation of Pd/C. By the use of the Pd/C-Ph2S catalytic system, olefins, acetylenes, and azides can be selectively reduced in the coexistence of aromatic carbonyls, aromatic halides, cyano groups, benzyl esters, and N-Cbz (benzyloxycarbonyl) protecting groups. The present method is promising as a general and practical chemoselective hydrogenation process in synthetic organic chemistry.
- Mori, Akinori,Mizusaki, Tomoteru,Miyakawa, Yumi,Ohashi, Eri,Haga, Tomoko,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
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p. 11925 - 11932
(2007/10/03)
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- N-phenpropylcuclopentyl-substituted glutaramide derivatives as inhibitors of neutral endopeptidase
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The invention relates to compounds of formula (I) for treating for example sexual dysfunction, wherein R1 is optionally substituted C1-6alkyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, hydrogen, C1-6alkoxy, —NR2 R3 or —NR4SO2R5; X is the linkage —(CH2)n— or —(CH2)q—O— (wherein Y is attached to the oxygen); wherein one or more hydrogen atoms in linkage X may be replaced independently by C1-4alkoxy; hydroxy; hydroxy(C1-3alkyl); C3-7cycloalkyl; carbocyclyl; heterocyclyl; or by C1-4alkyl optionally substituted by one or more fluoro or phenyl groups; n is 3, 4, 5, 6 or 7; and q is 2, 3, 4, 5 or 6; and Y is phenyl or pyridyl, each of which may be substituted; or two R8 groups on adjacent carbon atoms together with the interconnecting carbon atoms may form a fused optionally substituted 5- or 6-membered carbocyclic or heterocyclyic ring.
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