无溶剂条件下通过锌铜偶促进的Barbier反应合成羧酸酯
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  • 英文篇名:Synthesis of Esters via Barbier Reaction Mediated by Zinc Copper Couple under Solvent-Free Conditions
  • 作者:孟团结 ; 黄现强 ; 王进贤 ; 辛丽
  • 英文作者:Meng Tuanjie;Huang Xianqiang;Wang Jin-Xian;Xin Li;College of Chemistry and Chemical Engineering, Northwest Normal University;Key Laboratory of New Organic Materials synthesis, College of Chemistry and Chemical Engineering,Shangqiu Normal University;
  • 关键词:Barbier反应 ; 锌铜偶 ; 一锅法 ; 无溶剂
  • 英文关键词:Barbier reaction;;zinc copper couple;;one-pot;;solvent-free
  • 中文刊名:YJHU
  • 英文刊名:Chinese Journal of Organic Chemistry
  • 机构:西北师范大学化学化工学院;商丘师范学院化学化工学院有机新材料合成重点实验室;
  • 出版日期:2014-11-13 14:56
  • 出版单位:有机化学
  • 年:2015
  • 期:v.35;No.316
  • 基金:国家自然科学基金(No.U1204204)资助项目~~
  • 语种:中文;
  • 页:YJHU201503026
  • 页数:7
  • CN:03
  • ISSN:31-1321/O6
  • 分类号:220-226
摘要
在锌酮偶的促进下,通过Barbier反应以醛、溴代烃和酸酐为原料,在无溶剂非催化条件下三组分"一锅法"反应合成了一系列高烯丙基酯、高炔丙基酯和β-乙酰氧基酯类化合物.对反应条件及历程也进行了探讨.该方法具有反应条件温和、操作简单、产率高、原料易得、反应迅速的特点.
        A series of homoallyl esters, homopropargyl esters and β-acetoxyl esters were obtained via Barbier reaction from one pot three component reaction of aldehydes, bromohydrocarbons and anhydrides mediated by zinc copper couple under non-catalytic and solvent-free conditions. The studies on the reaction conditions and the reaction mechanism were also carried out. This protocol has advantages of mild conditions, simple work-up, high yield, easily available starting materials and fast reaction rate.
引文
[1](a)Shen,Z.-L.;Wang,S.-Y.;Chok,Y.-K.;Xu,Y.-H.;Loh,T.-P.Chem.Rev.2013,113,271.(b)Yus,M.;González-Gómez,J.C.;Foubelo,F.Chem.Rev.2011,111,7774.(c)Roy,U.K.;Roy,S.Chem.Rev.2010,110,2472.(d)Tan,X.-H.;Zhao,H.;Hou,Y.-Q.;Liu,L.;Guo,Q.-X.Chin.J.Org.Chem.2004,24,987(in Chinese).(谭翔晖,赵晖,侯永泉,刘磊,郭庆祥,有机化学,2004,24,987.)(e)Liao,L.-A.;Li,Z.-M.Chin.J.Org.Chem.2000,20,306(in Chinese).(廖联安,李正名,有机化学,2000,20,306.)(f)Gao,F.;Deng,X.-J.;Tang,Y.;Tang,J.-P.;Yang,J.;Zhang,Y.-M.Tetrahedron Lett.2014,55,880.
    [2](a)Jadhav,B.D.;Pardeshi,S.K.Tetrahedron Lett.2014,55,4948.(b)Dam,J.-H.;Fristrup,P.;Madsen,R.J.Org.Chem.2008,73,3228.(c)Yang,X.;Huang,J.;Zhu,F.;Li,H.Acta Chim.Sinica 2010,68,217(in Chinese).(杨旭石,黄建林,朱凤霞,李和兴,化学学报,2010,68,217.)(d)Zhang,Y.;Zhang,H.;Liu,L.-Y.;Wang,X.;Chang,W.-X.;Li,J.Chem.J.Chin.Univ.2012,33,2447(in Chinese).(张艳,张华,刘凌艳,王欣,常卫星,李靖,高等学校化学学报,2012,33,2447.)
    [3]Slaton,R.;Petrone,A.;Manchanayakage,R.Tetrahedron Lett.2011,52,5073.
    [4](a)Tanaka,K.;Toda,F.Chem.Rev.2000,100,1025.(b)Li,S.;Wang,J.-X.;Wen,X.;Ma,X.Tetrahedron 2011,67,849.(c)Wang,J.-X.;Jia,X.;Meng,T.;Xin,L.Synthesis 2005,2838.(d)Andrews,P.C.;Peatt,A.C.;Raston,C.L.Tetrahedron Lett.2004,45,2431.(e)Andrews,P.C.;Peatt,A.C.;Raston,C.L.Tetrahedron Lett.2002,43,7541.(f)Andrews,P.C.;Peatt,A.C.;Raston,C.L.Green Chem.2001,3,313.(g)Ma,X.;Wang,J.-X.;Li,S.;Wang,K.;Huang,D.Tetrahedron2009,65,8683.(h)Zhou,W.;Yan,W.;Wang,J.-X.;Wang,K.Synlett 2008,137.
    [5](a)Long,J.;Zhang,S.-F.;Wang,P.-P.;Zhang,X.-M.;Yang,Z.-J.;Zhang,Q.;Chen,Y.J.Med.Chem.2014,57,7098.(b)Ko,J.;Molinski,T.F.J.Org.Chem.2013,78,498.(c)Venkatesham,A.;Nagaiah,K.Tetrahedron:Asymmetry 2012,23,1186.(d)Su,S.;Rodriguez,R.A.;Baran,P.S.J.Am.Chem.Soc.2011,133,13922.(e)Pandey,S.K.;Ramana,C.V.J.Org.Chem.2011,76,2315.(f)Lorpitthaya,R.;Suryawanshi,S.B.;Wang,S.;Pasunooti,K.K.;Cai,S.;Ma,J.;Liu,X.-W.Angew.Chem.,Int.Ed.2011,50,12054.(g)Saloranta,T.;Leino,R.Tetrahedron Lett.2011,52,4619.(h)Cui,Q.;Wang,J.;Yang,H.;Xie,L.;Xu,X.Chin.J.Org.Chem.2010,30,1705(in Chinese).(崔庆,王娇,杨海申,谢龙观,徐效华,有机化学,2010,30,1705.)(i)Yang,M.;He,J.;Cheng,Y.;Jiang,S.Chin.J.Org.Chem.2013,33,1319(in Chinese).(杨梅,何江波,程永现,蒋晟,有机化学,2013,33,1319.)
    [6]Kouznetsov,V.V.;Méndez,L.Y.V.Synthesis 2008,491.
    [7]Soengas,R.G.;Silva,A.M.S.Synlett 2013,1949.
    [8]Du,Z.;Li,Y.;Wang,F.;Zhou,W.;Wang,J.-X.Tetrahedron Lett.2010,51,1745.
    [9]Meng,T.;Liu,L.;Ren,L.;Liu,X.;Wang,X.;Zhao,W.Chin.J.Org.Chem.2014,34,1588(in Chinese).(孟团结,刘澜涛,任利锋,刘新明,王晓娟,赵文献,有机化学,2014,34,1588.)
    [10]Shen,H.;Lu,X.;Jiang,K.-Z.;Yang,K.-F.;Lu,Y.;Zheng,Z.-J.;Lai,G.-Q.;Xu,L.-W.Tetrahedron 2012,68,8916.
    [11]Zhao,J.;Fang,H.;Zhou,W.;Han,J.;Pan,Y.J.Org.Chem.2014,79,3847.
    [12]Li,C.-J.;Zhang,W.-C.J.Am.Chem.Soc.1998,120,9102.
    [13](a)Anzalone,P.W.;Baru,A.R.;Danielson,E.M.;Hayes,P.D.;Nguyen,M.P.;Panico,A.F.;Smith,R.C.;Mohan,R.S.J.Org.Chem.2005,70,2091.(b)Yadav,J.S.;Subba Reddy,B.V.;Reddy,G.S.K.K.Tetrahedron Lett.2000,41,2695.(c)Yadav,J.S.;Subba Reddy,B.V.;Madhuri,C.;Sabitha,G.Chem.Lett.2001,18.
    [14]Meng,T.;Xin,L.;Wang,J.-X.Chin.J.Synth.Chem.2006,14,53(in Chinese).(孟团结,辛丽,王进贤,合成化学,2006,14,53.)
    [15]Chalecki,Z.;Guibe-Jampel,E.,Plenkiewicz,J.Synth.Commun.1997,27,1217.
    [16]Chen,C.;David,C.J.Chem.Soc.,Chem.Commun.1991,18,1289.
    [17]Masahiro,M.;Teruaki,M.Chem.Lett.1982,241.
    [18]Novokreshchennykh,V.D.;Mochalov,S.S.;Lukashova,E.A.;Shabarov,Y.S.J.Org.Chem.USSR 1984,20,96.
    [19]Kula,J.;Quang,T.B.;Sikora,M.Tetrahedron:Asymmetry 2000,11,943.

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