- Visible light promoted continuous flow photocyclization of 1,2-diketones
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The continuous flow Norrish-Yang photocyclization of 1,2-diketones has been developed and used for the synthesis of a large number of functionalized 2-hydroxycyclobutanones, under blue light irradiation and employing acetone as a solvent. This eco-friendly procedure represents a valid alternative to the reactions carried out in batches thus reducing the reaction times, the formation of secondary products and simplifying the purification steps. The use of differently substituted diketone compounds has allowed us to obtain a wide range of 2 and 3-functionalized cyclobutanones, thus allowing the evaluation of the scope and limitations of this procedure.
- Frongia, Angelo,Luridiana, Alberto,Porcu, Stefania,Ricci, Pier Carlo,Secci, Francesco
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supporting information
p. 3684 - 3689
(2020/06/03)
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- Magnetic magnetite nanoparticals catalyzed selective oxidation of Α-hydroxy ketones with air and one-pot synthesis of benzilic acid and phenytoin derivatives
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A clean and efficient protocol for selective oxidation of α-hydroxy ketones using magnetic magnetite nanoparticals (Fe3O4·MNPs) as catalyst with air as green oxidant has been developed. Application of Fe3O4·MNPs was also proved to be successful in one-pot synthesis of benzilic acid and phenytoin derivatives. The facile one-pot procedure enhanced the production efficiency, shortened the reaction time and minimized the chemical waste. Notably, the catalyst can be reused at least for five times without any appreciable loss of its activity.
- Li, Xiaona,Xia, Dandan,Wen, Zhiyong,Gong, Bowen,Sun, Maolin,Wu, Yue,Zhang, Jie,Sun, Jun,Wu, Yang,Bao, Kai,Zhang, Weige
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- Titanium-mediated reductive cross-coupling reactions of imines with nitriles: An efficient route for the synthesis of α-aminoketones or 1,2-diketones
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The reaction of imines with low-valent titanium species, generated in situ by using Ti(OiPr)4/2 c-C5H9MgCl reagent, affords titanium-imine complex, which can couple with nitriles to provide 2,5-diazatitanacyclop
- Chen, Haoyi,Fan, Guoqin,Li, Shi,Mao, Kebin,Liu, Yuanhong
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supporting information
p. 1593 - 1596
(2014/03/21)
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- Pyridazine-based N-heterocyclic carbene complexes and ruthenium-catalyzed oxidation reaction of alkenes
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[Ru2Cl(L)(CH3CN)4](PF6) 3 (1, L = 3,6-bis(N-(pyridylmethyl)imidazolylidenyl)pyridazine), [Cu3La3](PF6)3 (2, L a = 3-(N-(pyridylmethyl)imidazolylidenyl)-6-(N-(pyridylmethyl) imidazolylonyl)pyridazine), [Pd2(allyl)2L](PF 6)2 (3), [Pd2(allyl)2L b2](PF6)2 (4, Lb = N-pyridylmethylimidazole), and [NiLc2](PF 6)2 (5, Lc = 3-(N-(pyridylmethyl) imidazolylidenyl)-6-methoxylpyridazine) have been synthesized and fully characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction analysis. In complex 1, ligand L binds to two Ru(II) centers, forming a well-behaved Ru2(L)Cl plane with a five-membered metallocyclic ring. Complex 2 is trinuclear, containing a triangular Cu3 unit bonded together by three 3-(N-(pyridylmethyl)imidazolylidenyl)-6-(N-(pyridylmethyl) imidazolylonyl)pyridazine, where one imidazolylidene was oxidized into imidazolone. Deprotonation reaction with Ag2O in CH3CN and CH3OH resulted in C-N cleavage of the imidazolium salt, and subsequent reaction with [Pd(allyl)Cl]2 and Ni(PPh3) 2Cl2 gave 4 and 5, respectively. Dinuclear Ru(II)-NHC complex 1 exhibits excellent catalytic activity for the oxidation of alkenes into diketones.
- Liu, Xiaolong,Chen, Wanzhi
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p. 6614 - 6622
(2012/11/06)
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- Palladium-catalyzed carbonation-diketonization of terminal aromatic alkenes via carbon-nitrogen bond cleavage for the synthesis of 1,2-diketones
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A palladium-catalyzed carbonation-diketonization reaction of terminal alkenes via carbon-nitrogen bond cleavage under an atmosphere of oxygen has been developed. A series of 1,2-diketones were readily prepared from the reaction of aromatic terminal alkenes with nitroalkanes.
- Wang, Azhong,Jiang, Huanfeng,Li, Xianwei
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supporting information; experimental part
p. 6958 - 6961
(2011/10/02)
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- Ruthenium-catalyzed oxidation of alkenes at room temperature: A practical and concise approach to α-diketones
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Chemical equations presented. The catalytic oxidation of alkenes to α-diketones is unprecedented. A new oxidation of alkenes, catalyzed by a ruthenium complex, which allows an efficient route to α-diketones using TBHP as an oxidant is described. This methodology is highly functional group tolerant, is practically convenient, requires no additional ligand, and operates under mild conditions with short reaction times. Based upon experimental observations, a plausible mechanism is proposed.
- Chen, Shulin,Liu, Zhaojun,Shi, Erbo,Chen, Long,Wei, Wei,Li, Hong,Cheng, Yannan,Wan, Xiaobing
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supporting information; experimental part
p. 2274 - 2277
(2011/06/27)
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- Polymer-supported synthesis of α- and β-hydroxyketones through the formation of 1,3-dithiane intermediates
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The synthesis of polymer-supported 2-monosubstituted 1,3-dithianes from soluble copolymers bearing 1,3-propanedithiol groups, their lithiation, reactions with electrophiles such as aldehydes, ketones, α,β- unsaturated ketones and oxiranes, and cleavage of
- Bertini, Vincenzo,Lucchesini, Francesco,Pocci, Marco,Alfei, Silvana,Idini, Barbara
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body text
p. 1141 - 1144
(2009/04/06)
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- New oxidative transformations of alkenes and alkynes under the action of diacetoxyiodobenzene
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Treatment of alkenes and alkynes with diacetoxyiodobenzene activated by mineral and organic acids predominantly results in oxidative rearrangement. 1,4-Diphenylbutadiene in MeOH gives 3,4-dimethoxy-1,4-diphenylbut-1-ene.
- Yusubov,Zholobova,Filimonova,Chi, Ki-Whan
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p. 1735 - 1742
(2007/10/03)
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- Selective oxidation of aryl ketones to α-diketones with 4-aminoperoxybenzoic acid supported on silica gel in presence of air
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4-Aminoperoxybenzoic acid supported on silica gel in presence of air was found to be a selective and convenient oxidant for the oxidation of methylene groups in aryl ketones to convert them to α-diketones. Springer-Verlag 2004.
- Ghazanfari, Dadkhoda,Najafizadeh, Fariba,Khosravi, Fereshteh
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p. 1409 - 1413
(2007/10/03)
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- Oxidation of alkylphenylacetylenes and dialkylacetylenes on palladium catalysts in DMSO
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Alkylphenyl-and dialkylacetylenes are oxidized by the DMSO-PdCl2 or DMSO-Pd/C system to give the corresponding 1,2-diketones. Oxidation of these compounds, unlike that of diarylacetylenes, is less selective and is accompanied by the partial cle
- Yusubov,Filimonov,Chi, Ki-Whan
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p. 649 - 653
(2007/10/03)
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- Asymmetric reduction of α-keto esters and α-diketones with a bakers' yeast keto ester reductase
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Optically pure α-hydroxy esters and α-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers' yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the stereochemical course depends on the chain length of the alkyl substituent on the carbonyl group. An α-keto short alkanoic ester affords the corresponding (S)-hydroxy ester, whereas a long alkanoate yields the corresponding (R)-hydroxy ester. The reduction of α-diketones affords the corresponding (S)-2-hydroxy ketones regio- and stereoselectively.
- Kawai, Yasushi,Hida, Kouichi,Tsujimoto, Munekazu,Kondo, Shin-Ichi,Kitano, Kazutada,Nakamura, Kaoru,Ohno, Atsuyoshi
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- Synthesis of symmetrical and unsymmetrical 1,2-Diketones through cathodic intramolecular coupling of diesters
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Electroreduction of diesters [R1COO(CH2)2OCOR2] with Mg electrode has been found to give the corresponding unsymmetrical 1,2-Diketones (R1COCOR2) with excellent yields.
- Kashimura, Shigenori,Murai, Yoshihiro,Washika, Chise,Yoshihara, Daisuke,Kataoka, Yasuki,Murase, Hiroaki,Shono, Tatsuya
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p. 6717 - 6720
(2007/10/03)
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- A convenient preparation of symmetrical and unsymmetrical 1,2-diketones: Application to fluorinated phenytoin synthesis
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1,2-Diketones are efficiently produced in two steps by reaction of aldehydes with anions derived from 2-substituted dithianes followed by treatment of the resulting alcoholis with NBS in aqueous acetone; phenytoin derivatives were prepared from these diketones by a standard method involving treatment with urea and potassium hydroxide under reflux.
- Page,Graham,Park
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p. 7265 - 7274
(2007/10/02)
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- CHEMISTRY OF α-NITROEPOXIDES: SYNTHESIS OF USEFUL INTERMEDIATES VIA NUCLEOPHILIC RING OPENING OF α-NITROEPOXIDES
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Various α-nitroepoxides are converted into corresponding 1,2-diketones via two different ways of ring opening viz. with Pd(O) and with DMSO/BF3*EtO2 (or ClSiMe3).In addition to this, a variety of nucleophiles are reacted with α-nitrocyclopentene oxide 6 and α-nitrocyclohexene oxide 7 to form the corresponding α-substituted ketones which are useful intermediates in organic synthesis.Two of the products so obtained viz. 32 and 33 are also transformed further into optically active thialactones 38 and 39 respectively via baker's yeast reduction followed by lactonisation.
- Vankar, Yashwant D.,Shah, Kavita,Bawa, Anita,Singh, Surendra P.
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p. 8883 - 8906
(2007/10/02)
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- A Facile Conversion of α-Nitroepoxides into 1,2-Diones and α-Iodoketones
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1,2-Diones and α-iodoketones have been prepared from α-nitroepoxides by treatment with DMSO/BF3*Et2O followed by Et3N and BF3*Et2O/NaI respectively.
- Vankar, Yashwant D.,Saksena, Rajendra K.,Bawa, Anita
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p. 1241 - 1244
(2007/10/02)
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- SWERN OXIDATION OF α-KETOLS TO α-DIKETONES
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The Swern oxidation of acyclic and cyclic α-ketols delivered α-diketones or the tautomeric diosphenols in good yield.
- Kawada, Kenji,Gross, Raymond S.,Watt, David S.
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p. 777 - 786
(2007/10/02)
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