- Method for promoting synthesis of beta-hydroxyl selenide compound by visible light
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The invention relates to the technical field of organic synthetic chemistry, in particular to a method for promoting synthesis of a beta-hydroxyl selenide compound by visible light. The method comprises the following steps: A, sequentially adding a compound 1 and a compound 2 into a reactor; B, stirring the compound 1 and the compound 2 for reaction at a certain temperature under the irradiation of a light source under an open condition; C, after the reaction is finished, evaporating the solvent under reduced pressure to obtain a crude product; and D, carrying out column chromatography purification to obtain the beta-hydroxy selenide compound 3. According to the method, olefin and diselenide are used as raw materials, one of an acetonitrile/water mixed solvent and an acetone/water mixed solvent is used as a solvent, the reaction temperature is room temperature, and the beta-hydroxyl selenide compound is efficiently synthesized under the irradiation of a white fluorescent light source; compared with the traditional synthesis method, the method has the advantages that the reaction conditions are mild and can be smoothly carried out at room temperature; operation is simple, and all operations can be carried out in an open system; and raw materials are easy to obtain, the yield is high, functional group compatibility is good, and the substrate application range is wide.
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Paragraph 0070-0073
(2021/05/01)
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- Selenomethoxylation of Alkenes Promoted by Oxone
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We describe herein an alternative method for the selenomethoxylation of unactivated alkenes using Oxone as a stoichiometric oxidant. The electrophilic species of selenium were easily generated in situ by the reaction of diorganyl diselenides with Oxone. By this efficient and simple approach, β-methoxy-selenides were obtained in moderate to excellent yields at room temperature in an open flask, starting from alkenes by using methanol as both nucleophile and solvent. When a mixture of H2O/CH3CN was employed as the solvent, β-hydroxy-selenides were selectively obtained under mild conditions.
- Perin, Gelson,Santoni, Paolo,Barcellos, Angelita M.,Nobre, Patrick C.,Jacob, Raquel G.,Lenard?o, Eder J.,Santi, Claudio
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p. 1224 - 1229
(2018/03/21)
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- Preparation method of beta-hydroxyphenyl selenide compound
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The invention relates to the technical field of synthesis of organic compounds and particularly relates to a preparation method of a beta-hydroxyphenyl selenide compound. The preparation method comprises the step of with aryl boronic acid with a structure presented by a formula (I), elemental selenium and an ethylene oxide derivative presented by a formula (II) as the raw materials, and carrying out insertion reaction on elemental selenium in a reaction solvent under the common effect of a copper catalyst, silver salt and alkali, so as to obtain the beta-hydroxyphenyl selenide compound represented by a formula (III), wherein R1 and R2 are respectively independently selected from one of H, a benzene ring, a naphthalene ring, a heterocyclic ring, a substituted benzene ring, linear alkyl, branched chain, halogen, nitryl and a cyano group.
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Paragraph 0068; 0069; 0070; 0071-0076; 0159; 0160-0162
(2017/12/27)
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- Acidic hierarchical zeolite ZSM-5 supported Ru catalyst with high activity and selectivity in the seleno-functionalization of alkenes
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The acidic hierarchical zeolite ZSM-5 (HZSM-5-H) was synthesized for the preparation of a supported Ru catalyst (Ru/HZSM-5-H). The obtained Ru/HZSM-5-H catalyst shows high activity and product selectivity in the seleno-functionalization of alkenes compared to γ-Al2O3, basic ETS-10 and acidic microporous zeolite ZSM-5 supported Ru catalysts (Ru/γ-Al2O3, Ru/ETS-10 and Ru/HZSM-5, respectively), as well as a homogeneous RuCl3 catalyst. The relatively strong acidic sites in Ru/HZSM-5-H could benefit the adsorption of styrenes and the activation of the CC bond. Meanwhile, Ru4+ in Ru/HZSM-5-H could facilitate the formation of electrophilic selenium species as compared to Ru0 species. In addition, the Ru/HZSM-5-M catalyst exhibits broad substrate compatibility in the difunctionalization of alkenes.
- Dong, Hai,Zhang, Lei,Fang, Zhongxue,Fu, Wenqian,Tang, Ting,Feng, Yu,Tang, Tiandi
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p. 22008 - 22016
(2017/07/10)
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- A β- hydroxyl selenium etheration method for synthesizing compound of
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The invention relates to a synthetic method of Beta-hydroxyl selenide compound. The method includes: in organic solvent, in the presence of catalyst and alkali, allowing halogenated compound to react with elemental Se and epoxy compound to obtain Beta-hydroxyl selenide compound. The synthetic method has the advantages that reaction is simple, operating is simple, yield is high, the method is a novel one, a novel synthetic route is provided for the synthesis of the Beta-hydroxyl selenide compounds, and the method has good scientific research value and industrial potential.
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Paragraph 0076-0079
(2017/03/08)
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- Copper-Catalyzed Oxirane-Opening Reaction with Aryl Iodides and Se Powder
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Using Se powder as the selenating reagent, the copper-catalyzed double C-Se cross-coupling of aryl iodides, epoxides, and elemental selenium has been developed. This strategy provides a straightforward approach to the synthesis of β-hydroxy phenylselenides with excellent regioselectivity of the ring opening reaction. This process proceeds in generally good yields and is compatible with a broad range of functional groups.
- Min, Lin,Wu, Ge,Liu, Miaochang,Gao, Wenxia,Ding, Jinchang,Chen, Jiuxi,Huang, Xiaobo,Wu, Huayue
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p. 7584 - 7590
(2016/09/09)
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- Regioselective ring-opening reactions of 1,2-epoxides with thiols and arylselenols directly promoted by [Bmim]BF4
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Regioselective ring-opening reactions of 1,2-epoxides with ArSH and ArSeH promoted by ionic liquid [Bmim]BF4 were investigated. A variety of β-hydroxy selenides and β-hydroxy sulfides were obtained in excellent yields (81-99%) with good regiose
- Yang, Ming-Hua,Yan, Guo-Bing,Zheng, Yun-Fa
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supporting information; experimental part
p. 6471 - 6474
(2009/04/06)
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- Biocatalytic reduction of a racemic selenocyclohexanone by Brazilian basidiomycetes
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An efficient synthesis of the chiral cyclic secondary alcohols, trans-2-(phenylseleno)cyclohexanol 1a and cis-2-(phenylseleno)cyclohexanol 1a, was obtained by enzymatic reduction of 2-(phenylseleno)cyclohexanone 1 using whole fungal cells. Five strains of white-rot basidiomycetes were examined; Irpex lacteus CCB 196, Pycnoporus sanguineus CCB 196, Trametes rigida CCB 285, Trametes versicolor CCB 202 and Trichaptum byssogenum CCB 203. Cells of T. rigida CCB 285 gave alcohols cis-(RS)-1a and trans-(SS)-1a in high enantiomeric excesses (ca. 99%).
- Piovan, Leandro,Capelari, Marina,Andrade, Leandro H.,Comasseto, Joao V.,Porto, Andre L.M.
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p. 1398 - 1402
(2008/02/11)
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- Oxidative Cleavage of Diselenide by m-Nitrobenzenesulfonyl Peroxide. Novel Method for the Electrophilic Benzeneselenenylations of Olefins and Aromatic Rings
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Diphenyl diselenide was found to be readily converted into benzeneselenenyl-m-nitrobenzenesulfonate (PhSeOSO2C6H4NO2-m) by treating with m-nitrobenzenesulfonyl peroxide.When the selenenyl sulfonate thus formed was allowed to react in situ with olefins, such as cyclohexene, 1-octene, or styrene, in the presence of various nucleophiles, the adducts of benzeneselenenyl group and a nucleophile were obtained.As the nucleophiles water, methanol, acetic acid, phenol, and anisole could be employed; oxyselenenylated : R=H, Me, Ac, and Ph) and arylselenenylated : R=H and Me) adducts were afforded.Phenol gave oxyselenenylated products in cyclohexene or 1-octene and arylselenenylated products in styrene.Efficient intramolecular cyclizations of unsaturated alcohols and carboxylic acids were similarly performed by the selenenyl sulfonate to afford corresponding benzeneselenenylated cyclic ethers and lactones.The selenenyl sulfonate was also found to be a highly reactive benzeneselenenylating reagent for aromatic rings, such as anisole, phenol, acetanilide, toluene, and benzene.
- Yoshida, Masato,Sasage, Shuichi,Kawamura, Kyoko,Suzuki, Takashi,Kamigata, Nobumasa
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p. 416 - 422
(2007/10/02)
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- On The Reactions of Benzeneseleninic Anhydride With Monosubstituted Hydrazones. Evidence for Radical Pathways.
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The known oxidation of mono-substituted hydrazones by benzeneseleninic anhydride has been studied using 77Se and 13C NMR spectroscopy.The intermediates in the reaction have been identified.Good evidence that certain steps in these reactions are radical in character has been secured.
- Barton, Derek H. R.,Okano, Takashi,Parekh, Shyamal I.
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p. 1823 - 1836
(2007/10/02)
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- Regioselective Oxyselenenylation
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The regioselective oxyselenenylation of terminal olefins or cycloalkenes was achieved via olefin oxymercuration and subsequent radical substitution by selenenylating reagent such as S-benzoyl Se-phenyl selenosulfide, diphenyl diselenide, or phenylselenocy
- Toru, Takeshi,Yamada, Yoshio,Maekawa, Eturo,Ueno, Yoshio
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p. 1827 - 1830
(2007/10/02)
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- SYNTHESIS OF 2-NITROALKYL PHENYL SELENIDES AND THEIR CONVERSION TO NITROALKENES
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Treatment of alkenes with benzeneselenenyl bromide followed by addition of silver nitrite provided a mixture of 2-nitroalkyl and 2-hydroxyalkyl phenyl selenides.Oxidation of the former selenides with hydrogen peroxide gave nitroalkenes in 90-93 percent yields.
- Hayama, Takashi,Tomoda, Shuji,Takeuchi, Yoshito,Nomura, Yujiro
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p. 1109 - 1112
(2007/10/02)
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- A DIRECT PHENYLSELENENYLATION OF ALKYL HALIDES, ALKENYL SULFONATES, AND EPOXIDES BY AN ELECTROREDUCTION OF DIPHENYL DISELENIDE
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A convenient procedure for phenylselenenylation of alkyl halides, alkenyl sulfonates, and epoxides with phenyl selenide anion was accomplished by electroreduction of diphenyl diselenide in a protic solvent.
- Torii, Sigeru,Inokuchi, Tsutomu,Asanuma, Goro,Sayo, Noboru,Tanaka, Hideo
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p. 867 - 868
(2007/10/02)
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