- Asymmetric Transfer Hydrogenation of Diaryl Ketones with Ethanol Catalyzed by Chiral NCP Pincer Iridium Complexes
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The use of a chiral (NCP)Ir complex as the precatalyst allowed for the discovery of asymmetric transfer hydrogenation of diaryl ketones with ethanol as the hydrogen source and solvent. This reaction was applicable to various ortho-substituted diaryl keontes, affording benzhydrols in good yields and enantioselectivities. This protocol could be carried out in a gram scale under mild reaction conditions. The utility of the catalytic system was highlighted by the synthesis of the key precursor of (S)-neobenodine.
- Huang, Zheng,Liu, Guixia,Qian, Lu,Tang, Xixia,Wang, Yulei
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supporting information
(2022/02/23)
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- Method for synthesizing biaryl ketone compounds through carbonylation by taking chloroform as carbonyl source without transition metal participation
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The invention discloses a method for synthesizing biaryl ketone compounds through carbonylation by taking chloroform as a carbonyl source without transition metal participation. The method disclosed by the invention comprises the following steps: carrying out a cross coupling reaction on aryl halides, aromatic boron compounds and chloroform serving as the carbonyl source in an aqueous solution ofsolvent alcohol or alcohol in the presence of alkali, acids and iodides without transition metal participation, thereby obtaining the biaryl ketone compounds. According to the method for preparing thebiaryl ketone compounds through the cross coupling reaction, disclosed by the invention, the most obvious advantage is that no transition metal catalyst is used and the chloroform serves as the carbonyl source; the method has the advantages such as low cost and zero metal residue caused by no need of the transition metal catalyst; the carbonyl source is safe, cheap and easy to treat; the reactioncondition is mild, and the selectivity is high; the substrate source is wide and stable; and the compatibility of functional groups of the substrate is excellent, the application range of the substrate is wide, and under the optimized reaction conditions, the separation yield of the target product reaches 95%.
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Paragraph 0077; 0078-0079; 0113
(2018/12/02)
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- Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C–CN Bond Activation
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A Pd-catalyzed Suzuki–Miyaura cross-coupling reaction between arylboronic acids and α-iminonitriles has been developed. The reaction proceeds through selective activation of the C–CN bond, tolerates a wide range of substituents, and delivers the versatile ketone products in moderate to excellent yields.
- Liu, Kui,Tao, Shou-Wei,Qian, Chun,Zhu, Yong-Ming
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supporting information
p. 4769 - 4775
(2018/09/06)
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- A iron catalytic carbonylation of two fragrant ketone method (by machine translation)
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The invention discloses an iron catalytic carbonylation of the second category of ketone compounds, which belongs to the technical field of catalytic synthesis. The present invention in aqueous solution in the solvent flux, in alkali, under the action of the acid and iodide, addition of an iron catalyst, catalytic aryl halogenide, or four the halogen imitatesfragrant boron apperception compound with carbon halide carbonyl source direct cross-coupling reaction for preparing two fragrant armor ketone compound. Coupling reaction of the present invention for the preparation of two fragrant armor ketone compounds, with carbonyl source safe, cheap and easy to process; catalyst source is extensive, cheap and toxicity is small; the reaction does not need good of the ligands and; mild reaction conditions and selectively high; the substrate is extensive and stability; good substrate functional group compatibility of wide application range of the substrate; the reaction medium can be green and recycling. In the optimized under the reaction conditions, the yield of the target product separation up to 94%. (by machine translation)
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Paragraph 0065; 0066; 0103
(2017/01/31)
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- Chloro-ruthenium complexes with carbonyl and N-(aryl)pyridine-2-aldimines as ancillary ligands. Synthesis, characterization and catalytic application in C-C cross-coupling of arylaldehydes with arylboronic acids
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Reaction of N-(aryl)pyridine-2-aldimines (L-R, R = OCH3, CH 3, H, Cl and NO2) with [Ru(CO)2Cl 2]n in refluxing ethanol affords a group of complexes of type [Ru(L-R)(CO)2Cl2]. In these complexes the diimine ligands (L-R) are coordinated to the metal center as NN-donors forming five-membered chelate rings, the carbonyls are mutually cis and the two chlorides are trans. Crystal structure of [Ru(L-OCH3)(CO) 2Cl2] has been determined. All the complexes show characteristic 1H NMR signals, and in dichloromethane solution they display intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows an irreversible oxidation of the metal center within 1.15-1.23 V vs SCE, and reduction(s) of the diimine ligand within -0.70 to -0.96 V vs SCE. The [Ru(L-R)(CO)2Cl2] complexes efficiently catalyze cross-coupling of arylaldehydes with arylboronic acids yielding diaryl ketones.
- Dey, Bikash Kali,Dutta, Jayita,Drew, Michael G.B.,Bhattacharya, Samaresh
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p. 176 - 184
(2014/01/06)
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- Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst
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Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.
- Parella, Ramarao,Naveen,Kumar, Amit,Babu, Srinivasarao Arulananda
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p. 1738 - 1742
(2013/03/28)
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- Analogues of fenarimol are potent inhibitors of trypanosoma cruzi and are efficacious in a murine model of chagas disease
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We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC50s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.
- Keenan, Martine,Abbott, Michael J.,Alexander, Paul W.,Armstrong, Tanya,Best, Wayne M.,Berven, Bradley,Botero, Adriana,Chaplin, Jason H.,Charman, Susan A.,Chatelain, Eric,Von Geldern, Thomas W.,Kerfoot, Maria,Khong, Andrea,Nguyen, Tien,McManus, Joshua D.,Morizzi, Julia,Ryan, Eileen,Scandale, Ivan,Thompson, R. Andrew,Wang, Sen Z.,White, Karen L.
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p. 4189 - 4204
(2012/07/27)
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- Fatty acid amide hydrolase inhibitors. 3: Tetra-substituted azetidine ureas with in vivo activity
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We describe here our attempts to optimise the human fatty acid amide hydrolase (FAAH) inhibition and physicochemical properties of our previously reported tetrasubstituted azetidine urea FAAH inhibitor, VER-156084. We describe the SAR of a series of analogues and conclude with the demonstration of in vivo dose-dependant FAAH inhibition in an anandamide-loading study in rats.
- Roughley, Stephen D.,Browne, Helen,MacIas, Alba T.,Benwell, Karen,Brooks, Teresa,D'Alessandro, Jalanie,Daniels, Zoe,Dugdale, Sarah,Francis, Geraint,Gibbons, Ben,Hart, Terance,Haymes, Timothy,Kennett, Guy,Lightowler, Sean,Matassova, Natalia,Mansell, Howard,Merrett, Angela,Misra, Anil,Padfield, Anthony,Parsons, Rachel,Pratt, Robert,Robertson, Alan,Simmonite, Heather,Tan, Kiri,Walls, Steven B.,Wong, Melanie
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scheme or table
p. 901 - 906
(2012/03/11)
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- "Greener" Friedel-Crafts acylations: A metal- and halogen-free methodology
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Chemical equations presented. The utility of methanesulfonic anhydride for promoting the Friedel-Crafts acylation reaction of aryl and alkyl carboxylic acids is disclosed. This reagent allows the preparation of aryl ketones in good yield with minimal waste containing no metallic or halogenated components, clearly differentiating it from other available methodologies.
- Wilkinson, Mark C.
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supporting information; experimental part
p. 2232 - 2235
(2011/06/24)
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- Ytterbium triflate catalyzed Friedel-Crafts reaction: Facile synthesis of diaryl ketones
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Friedel-Crafts reaction of aromatic compounds (benzenes, thiophene, furan, pyrrole, naphthalene, and benzothiophene) with bis(trichloromethyl) carbonate [BTC] was efficiently catalyzed by ytterbium triflate [Yb(OTf)3] to give diaryl ketones wit
- Su, Weike,Jin, Can
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p. 4249 - 4256
(2007/10/03)
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- Method for acylation or sulphonylation of an aromatic compound
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The present invention relates to a process for the acylation or sulphonylation of an aromatic compound. More particularly, the invention relates to a process for the acylation or sulphonylation of an activated or deactivated aromatic compound. The invention is applied to the preparation of aromatic ketones or sulphones. The process for the acylation or sulphonylation of an aromatic compound which consists in reacting at least one aromatic compound with an acylating or sulphonylating agent, in the presence of a Friedel-Crafts catalyst is characterized in that the acylation or sulphonylation reaction is carried out in liquid phase under microwave irradiation.
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Page column 18,19
(2008/06/13)
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- Friedel-crafts reaction of BIS(Trichloromethyl)carbonate for the preparation of benzophenones
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Benzophenones (RC6H4COC6H4R, R=H, Cl, CH3 or (CH3)2N) have been prepared by the Friedel-Crafts reactions of aromatic compounds C6H5R with bis(trichloromethy
- Peng, Xiaojun,Wang, Jingyun,Cui, Jingnan,Zhang, Rong,Yan, Ying
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p. 2361 - 2367
(2007/10/03)
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- A new catalytic oxidation of diarylmethanes mediated by 2,2',3,3',5,5'- hexaphenyl-(1,1'-biphenyl)-4,4'-dioxyl
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Diarylmethanes were catalytically oxidized with oxygen to benzophenones with a Cu(I)CI catalyst in butyronitrile as solvent in the presence of the mediating agent 2,2',3,3',5,5'-hexaphenyl-(1,1'-biphenyl)-4,4'-dioxyl 1, which was generated in situ from 2,2',3,3',5,5'-hexaphenyl-(1,1'-biphenyl)- 4-4'-diol 4.
- Barbiero,Kim,Hay
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p. 5833 - 5836
(2007/10/02)
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- Process for the preparation of benzophenones
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A process for the preparation of benzophenones. A compound of the formula COX4 X5, where X4 and X5, which may be identical or different are halogen atoms, is reacted, in liquid hydrofluoric acid, with a deactivated benzene derivative, in the presence of boron trifluoride in such amount that the absolute pressure of boron trifluoride in the reaction space is at least one bar.
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- Process for the acylation of halo- or trihalomethylbenzenes
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A process for the acylation of halo- or trihalomethylbenzenes, wherein a halo- or trihalomethylbenzene is reacted with a carboxylic acid, a precursor or a derivative thereof in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.
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- Carboxylic Trifluoromethanesulfonic Anhydrides as Highly Effective Acylation Agents. - Perfluoroalkanesulfonic Acid Catalyzed Acylation of Arenes
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Arene- and alkanecarboxylic trifluoromethanesulfonic anhydrides 2 and 5 are highly effective acylation agents, which react without Friedel-Crafts catalysts even with deactivated aromatics to yield aryl ketones 3 and 6, respectively.Acylation of arenes with carbonyl chlorides 4 and catalytic amounts of perfluoroalkanesulfonic acid gives ketones 3 and 6, resp., in good yields.Under similar conditions other strong Broensted acids show a considerably smaller degree of catalytic effect.
- Effenberger, Franz,Sohn, Erich,Epple, Gerhard
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p. 1195 - 1208
(2007/10/02)
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- ACTION OF HETEROPOLY ACID AND RELATED OXIDES IN ACYLATION OF CHLOROBENZENE WITH o-CHLOROBENZOYL CHLORIDE
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Heteropoly acids, MoO3, and calcined FeSO4 have been found to catalyze the acylation of chlorobenzene with o-chlorobenzoyl chloride.A kinetic study revealed that those catalysts are not active in their original forms, but the metal chlorides or metal complexes formed by reacting with chlorine are active for the acylation reaction.
- Yamaguchi, Tsutomu,Mitoh, Akimi,Tanabe, Kozo
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p. 1229 - 1232
(2007/10/02)
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