醋酸酮催化二硫醚与四氢呋喃的氧化偶联反应

应用化学, 2015, 32(11): 1253-1258. doi: 10.11944/j.issn.1000-0518.2015.11.150124

醋酸酮催化二硫醚与四氢呋喃的氧化偶联反应

周芸 ^1, , 刘卉 ^2, , 何艳 ^3, , 李爱桃 ^4, , 陶李明 ^5,

1.湘南学院化学与生命科学系,湘南稀贵金属化合物及其应用湖南省重点实验室湖南郴州,423000

2.湘南学院化学与生命科学系,湘南稀贵金属化合物及其应用湖南省重点实验室湖南郴州,423000

3.湘南学院化学与生命科学系,湘南稀贵金属化合物及其应用湖南省重点实验室湖南郴州,423000

4.湘南学院化学与生命科学系,湘南稀贵金属化合物及其应用湖南省重点实验室湖南郴州,423000

5.湘南学院化学与生命科学系,湘南稀贵金属化合物及其应用湖南省重点实验室湖南郴州,423000

基金项目: 湖南省重点建设学科(湘教发[2011]76) 郴州市科技计划项目(CZ2014038)Supported by the Construct Programme of the Key Discipline in Hu'nan Province, the Science and Technology Department of Hu'nan Province Project(2012TP4021-3) 湖南省科技厅计划项目(2012TP4021-3) Chenzhou Science and Technology Bureau Project(CZ2014038)

关键词：醋酸酮 , 二硫醚 , 四氢呋喃 , 氧化偶联反应 , 双氧水

Copper Acetate Catalyzed Oxidative Coupling of Disulfides with Tetrahydrofuran

Keywords： copper acetate , disulfides , tetrahydrofuran , oxidative coupling reaction , H2O2

研究了醋酸酮催化二硫醚与四氢呋喃以氧化偶联反应构建C—S键.结果表明,在醋酸酮(10％摩尔分数)、二硫醚(0.5 mmol)、四氢呋喃(2 mL)和双氧水(35％,2倍化学计量),反应温度120℃条件下,二硫醚与四氢呋喃能够顺利地发生氧化偶联反应,生成相应的C—S键化合物,合成硫醚类化合物产率中等到良好.该反应以双氧水为氧化剂,具有环境友好等特性.

参考文献

[1]	Joyce, LL;Batey, RA.Heterocycle Formation via Palladium-Catalyzed Intramolecular Oxidative C-H Bond Functionalization: An Efficient Strategy for the Synthesis of 2-Aminobenzothiazoles[J].Organic letters,200913(13):2792-2795.
[2]	Yan Li;Weiliang Bao.A Highly Efficient, Metal-Free and Convenient Diarylallyl Ether/Thloether Formation via Oxidative C-H Activation[J].Advanced synthesis & catalysis,20096(6):865-868.
[3]	Tang, R.-Y.;Xie, Y.-X.;Xie, Y.-L.;Xiang, J.-N.;Li, J.-H..TBHP-mediated oxidative thiolation of an sp ~3 C-H bond adjacent to a nitrogen atom in an amide[J].Chemical communications,201148(48):12867-12869.
[4]	Jazzar, R;Hitce, J;Renaudat, A;Sofack-Kreutzer, J;Baudoin, O.Functionalization of Organic Molecules by Transition-Metal-Catalyzed C(sp(3))-H Activation[J].Chemistry: A European journal,20109(9):2654-2672.
[5]	Suematsu, H;Katsuki, T.Iridium(III) Catalyzed Diastereo- and Enantioselective C-H Bond Functionalization[J].Journal of the American Chemical Society,200940(40):14218-14219.
[6]	Yoo, E.J.;Ma, S.;Mei, T.-S.;Chan, K.S.L.;Yu, J.-Q..Pd-catalyzed intermolecular C-H amination with alkylamines[J].Journal of the American Chemical Society,201120(20):7652-7655.
[7]	Haitao Zhu;Pinhong Chen;Guosheng Liu.Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile[J].Journal of the American Chemical Society,20145(5):1766-1769.
[8]	Sun, H.;Zhang, Y.;Guo, F.;Zha, Z.;Wang, Z..Regioselective oxyalkylation of vinylarenes catalyzed by diatomite-supported manganese oxide nanoparticles[J].The Journal of Organic Chemistry,20127(7):3563-3569.
[9]	Wen-Ting Wei;Ming-Bo Zhou;Jian-Hong Fan.Synthesis of Oxindoles by Iron-Catalyzed Oxidative 1,2-Alkylarylation of Activated Alkenes with an Aryl C(sp~2)-H Bond and a C(sp~3)-H Bond Adjacent to a Heteroatom[J].Angewandte Chemie,201313(13):3638-3641.
[10]	Brindaban C.Ranu;Tanmay Mandal.Indium(I) iodide promoted cleavage of dialkyl/diaryl disulfidcs and subsequent anti-Markovnikov addition to styrenes: a new route to linear thioethers[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,200638(38):6911-6914.
[11]	Ranu BC;Mandal T.Water-promoted highly selective anti-Markovnikov addition of thiols to unactivated alkenes[J].Synlett,20076(6):925-928.
[12]	Zhang YM;Fu H;Jiang YY;Zhao YF.Copper-catalyzed amidation of Sp(3) C-H bonds adjacent to a nitrogen atom[J].Organic letters,200719(19):3813-3816.
[13]	Ye, X.;Xie, C.;Pan, Y.;Han, L.;Xie, T..Copper-catalyzed synthesis of α-amino imides from tertiary amines: Ugi-type three-component assemblies involving direct functionalization of sp~3 C-Hs adjacent to nitrogen atoms[J].Organic letters,201019(19):4240-4243.

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