68427-26-9Relevant academic research and scientific papers
Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor
Zhang, Deliang,Iwai, Tomohiro,Sawamura, Masaya
supporting information, p. 5867 - 5872 (2019/08/26)
The iridium-catalyzed transfer hydrogenation of alkenes using 1,4-dioxane as a hydrogen donor is described. The use of 1,2-bis(dicyclohexylphosphino)ethane (DCyPE), featuring bulky and highly electron-donating properties, led to high catalytic activity. A polystyrene-cross-linking bisphosphine PS-DPPBz produced a reusable heterogeneous catalyst. These homogeneous and heterogeneous protocols achieved chemoselective transfer hydrogenation of alkenes over other potentially reducible functional groups such as carbonyl, nitro, cyano, and imino groups in the same molecule.
Copper catalyzed oxygen assisted C(CNOH)-C(alkyl) bond cleavage: A facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids
Sathyanarayana, Pochampalli,Ravi, Owk,Muktapuram, Prathap Reddy,Bathula, Surendar Reddy
supporting information, p. 9681 - 9685 (2015/09/28)
A novel copper-catalyzed aerobic oxidative C(NOH)-C(alkyl) bond cleavage reaction of aryl/aralkyl/vinyl ketones for the synthesis of aromatic/acrylic acids is described. A series of ketones having aryl/aralkyl/vinyl at the one end and methyl to any higher alkyl at the other end can be selectively cleaved and converted into the corresponding acids via oxime intermediates.
Nickel-catalyzed regio- and stereoselective reductive coupling of Oxa- and azabicyclic alkenes with enones and electron-rich alkynes
Mannathan, Subramaniyan,Cheng, Chien-Hong
supporting information, p. 2239 - 2246 (2014/07/21)
A nickel-catalyzed regio- and stereoselective reductive coupling of oxa- and azabicyclic alkenes with activated alkenes and electron-rich alkynes is described. Thus, 7-oxabenzonorbornadienes underwent reductive coupling with various vinyl ketones such as ethyl, methyl, propyl and α-methyl- substituted vinyl ketones, in the presence of a nickel(II) iodide (NiI 2), zinc (Zn), and water catalyst system in acetonitrile at 50 °C for 14 h to afford 2-alkylnaphthalenes in good to excellent yields. Under similar reaction conditions, 7-azabenzonorbornadiene derivatives provided cis-2-alkyl-1,2-dihydronaphthalene derivatives in high yields. On the other hand, the nickel(II) iodide, tris(4-fluorophenyl)phoshine [P(4-FC 6H4)3] and zinc catalyst system successfully catalyzed the reductive coupling reaction of electron-rich alkynes, with 7-aza- and 7-oxabenzonorbornadienes to give cis-2-alkenyl-1,2-dihydronaphthalene derivatives in good to excellent yields. In the reaction, a mild reducing agent (zinc) and simple hydrogen source (water) were used.
Aerobic oxidative coupling between carbon nucleophiles and allylic alcohols: A strategy to construct β-(hetero)aryl ketones and aldehydes through hydrogen migration
Huang, Liangbin,Qi, Ji,Wu, Xia,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 15462 - 15466 (2013/11/19)
Wacker heck of a reaction: A highly efficient PdII-catalyzed intermolecular oxidative-coupling reaction is reported, inspired by the fundamental Heck and Wacker processes. The (hetero)aryl-PdX species, originating from C-H activation step or desulfonyl hydrazides, coupled with allylic alcohols by using oxygen as the sole oxidant (see scheme). Copyright
Cobalt-salen complex-catalyzed oxidative generation of alkyl radicals from aldehydes for the preparation of hydroperoxides
Watanabe, Eiichi,Kaiho, Atsushi,Kusama, Hiroyuki,Iwasawa, Nobuharu
supporting information, p. 11744 - 11747 (2013/09/02)
Catalytic generation of alkyl radicals from aldehydes via oxidative deformylation was realized using a cobalt-salen complex with H2O 2. The deformylation was thought to proceed through homolytic cleavage of peroxohemiacetal intermediates to provide even primary alkyl radicals under mild conditions. Variously substituted and functionalized hydroperoxides were obtained from corresponding aldehydes in good yield.
Electron-deficient phosphines accelerate the heck reaction of electronrich olefins in ionic liquid
Liu, Shifang,Saidi, Ourida,Berry, Neil,Ruan, Jiwu,Pettman, Alan,Thomson, Nick,Xiao, Jianliang
scheme or table, p. 60 - 64 (2010/04/23)
Using various substrates and ligands, we show that electron-deficient, bidentate phosphines are the ligands of choice for palladium-catalyzed arylation of electron-rich olefins. This is in contrast to the reaction of electron-deficient olefins, which bene
A new, efficient and stereoselective synthesis of tricyclic and tetracyclic compounds by samarium diiodide induced cyclisations of naphthyl-substituted arylketones-an easy access to steroid-like skeletons
Aulenta, Francesca,Berndt, Mathias,Bruedgam, Irene,Hartl, Hans,Soergel, Sebastian,Reissig, Hans-Ulrich
, p. 6047 - 6062 (2008/02/13)
In this report, we present the application of samarium diiodide induced cyclisations of naphthyl-substituted ketones towards an easy and stereoselective access to tri- and tetracyclic-functionalised compounds. Typical naphthalene derivatives were studied to investigate the scope and limitations of this novel cyclisation process. The model substrates studied demonstrate that the samarium ketyl cyclisations are essentially restricted to the formation of six-membered rings. The diastereoselectivity of these reactions is strongly influenced by the connection of the alkyl side chain to the naphthalene core. γ-Naphth-1-yl-substituted ketones furnished cyclisation products, such as 17 or 22-26, as single diastereomers, whereas γ-naphth-2-yl-substituted precursors gave mixtures of diastereomers - as demonstrated by the conversion of model compound 10 into tricyclic products 18 a/18 b, or that of cyclohexanone derivative 33 into tetracyclic diastereomers 34 a/34 b. Cyclic ketones as ketyl precursors furnished steroid-like tetracyclic skeletons; however, due to the cis/cis fusion of rings B/C and C/D these products have an "unnatural" bowl-like shape. Several of the cyclisation products have been identified by X-ray analyses, which not only proved the constitutions, but also the relative configurations and the preferred conformations. Steroid analogue 23 was subjected to subsequent transformations, which demonstrate that the styrene-like double bond of such compounds can be used for further structural diversification. First attempts to synthesise related azasteroids by incorporating nitrogen atoms into the ketone moiety are also reported. Thus, pyrrolidine derivatives 44 and 47 as well as piperidine derivatives 50 and 52 were subjected to samarium diiodide induced cyclisations. The expected tetracyclic products 48, 49 a/49 b, 51 and 53 a/53 b were obtained in moderate to good yields. The stereoselectivities observed follow the rules already established for the all-carbon precursors. The resulting products, bearing a nitrogen atom in ring D, are interesting azasteroid analogues with "unnatural" configuration.
2,3,4-substituted cyclopentanones as therapeutic agents
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Page/Page column 26, (2010/11/08)
Disclosed herein are compounds comprising or a pharmaceutically acceptable salt or a prodrug thereof; wherein Y, A, B, J, and E are further described. Methods, compositions, and medicaments related thereto are also disclosed.
Phosphonic acid derivatives
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, (2008/06/13)
A phosphonic acid derivative which is useful for medically treating hyperlipemia, represented by the following general formula (I) or a pharmacologically acceptable salt thereof: STR1 Representative example of the compound according to the present invention is one represented by the following formula: STR2
Palladium(II)-Catalyzed Conjugate Addition of Aromatics to α,β-Unsaturated Ketones and Aldehydes with Arylantimony Compounds
Cho, Chan Sik,Motofusa, Shin-Ichi,Ohe, Kouichi,Uemura, Sakae
, p. 2341 - 2348 (2007/10/03)
Triarylstibines react with α,β-unsaturated ketones and aldehydes in acetic acid at room temperature in the presence of AgOAc and a catalytic amount of Pd(OAc)2 to afford the conjugate addition products (the formal hydroarylated compounds to an olefinic part) in good yields. In contrast, diarylantimony chlorides, arylantimony dichlorides, and diphenylantimony acetate react with the enones and enals even in the absence of AgOAc to afford the same products in higher yields compared with those from triarylstibines. These are new C-C bond-forming reactions using arylantimony(III) compounds in which the formation of a palladium enolate or a trivalent antimony enolate is proposed as an intermediate.
