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有机高价碘化学简介及其应用
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  • 英文篇名:Introduction of Hypervalent Iodine Chemistry and Its Application
  • 作者:刘丹 ; 贺家豪 ; 张弛
  • 英文作者:LIU Dan;HE Jiahao;ZHANG Chi;National Pesticide Engineering Research Center (Tianjin), Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University;
  • 关键词:高价碘化学 ; 合成应用 ; 有机合成 ; 材料化学 ; 工业合成
  • 英文关键词:Hypervalent iodine chemistry;;Synthetic application;;Organic synthesis;;Material chemistry;;Industrial synthesis
  • 中文刊名:DXHX
  • 英文刊名:University Chemistry
  • 机构:南开大学化学学院元素有机化学国家重点实验室天津化学化工协同创新中心农药国家工程研究中心(天津);
  • 出版日期:2019-02-28
  • 出版单位:大学化学
  • 年:2019
  • 期:v.34
  • 基金:国家自然科学基金(21472094,21772096);; 天津市自然科学基金(17JCYBJC20300)
  • 语种:中文;
  • 页:DXHX201902001
  • 页数:16
  • CN:02
  • ISSN:11-1815/O6
  • 分类号:3-18
摘要
近几十年来,有机高价碘化学蓬勃发展,有机高价碘试剂也受到化学合成工作者的广泛关注,关于有机高价碘试剂的反应性研究也获得了迅猛发展。有机高价碘试剂作为绿色、高效、多功能化的氧化剂,通常容易制备且操作简单,与已有的合成方法相比,该类试剂参与的反应表现出了许多独特的优点,并且具有与汞、铬、铅、铊等重金属试剂类似的反应性,但却没有这些试剂所带来的毒性和环境污染问题。本文介绍了有机高价碘化学的起源与发展,高价碘试剂的结构特点与分类,高价碘试剂在有机合成、材料化学及工业合成中的应用。
        In recent decades, hypervalent iodine chemistry has witnessed its explosive development. Hypervalent iodine reagents have drawn considerable attentions and their reactivities have been continuously explored.Hypervalent iodine reagents, featuring facile availability and easy handling, offer multiple advantages over established methods as a green, efficient and multipurpose oxidant. The reactivities of hypervalent iodine reagents are similar to derivatives of mercury, chromium, lead, thallium and other heavy metals, but the toxicity and environmental problems are less than those of the heavy metal reagents. This paper mainly introduces the development of hypervalent iodine chemistry, the structure and classification of hypervalent iodine reagents and the synthetic application of hypervalent iodine reagents in organic chemistry, materials chemistry and industrial synthesis.
引文
[1]Courtois,B.Anal.Chim.1813,88,304.
    [2]Greenwood,N.N.;Earnshaw,A.Chemistry of the Elements,2nd ed.;Elsevier:Oxford,1997,789-887.
    [3]Willgerodt,C.J.Prakt.Chem.1886,33,154.
    [4]Willgerodt,C.Berichte der Deutschen Chemischen Gesellschaft 1892,25,3494.
    [5]Hartmann,C.;Meyer,V.Berichte der Deutschen Chemischen Gesellschaft 1894,27,426.
    [6]Willgerodt,C.Die Organischen Verbindungen mit Mehrwertigen Jod;Ferdinand Enke Verlag:Stuttgart,1914.
    [7]Dess,D.B.;Martin,J.C.J.Org.Chem.1983,48,4155.
    [8](a)Han,Y.;Zhang,C.Tetrahedron Lett.2018,59,3052.(b)Yoshimura,A.;Zhdankin,V.V.Chem.Rev.2016,116,3328.(c)Li,Y.;Hari,D.P.;Vita,M.V.;Waser,J.Angew.Chem.Int.Ed.2016,55,4436.(d)Duan,Y.;Jiang,S.;Han,Y.;Sun,B.;Zhang,C.Chin.J.Org.Chem.2016,36,1973.(e)Chen,J.;Qu,H.M.;Peng,J.;Chen,C.Chin.J.Org.Chem.2015,35,937.(f)Charpentier,J.;Fruh,N.;Togni,A.Chem.Rev.2015,115,650.(g)Singh,F.V.;Wirth,T.Chem.-Asian J.2014,9,950.(h)Brown,M.;Farid,U.;Wirth,T.Synlett.2013,24,424.(i)Duschek,A.;Kirsch,S.F.Angew.Chem.Int.Ed.2011,50,1524.(j)Merritt,E.A.;Olofsson,B.Synthesis 2011,2011,517.(k)Brand,J.P.;Gonzalez,D.F.;Nicolai,S.;Waser,J.Chem.Commun.2011,47,102.(l)Dohi,T.;Kita,Y.Chem.Commun.2009,45,2073.(m)Zhdankin,V.V.;Stang,P.J.Chem.Rev.2008,108,5299.(n)Wirth,T.Angew.Chem.Int.Ed.2005,44,3656.(o)Zhdankin,V.V.;Stang,P.J.Chem.Rev.2002,102,2523.
    [9](a)Zhdankin,V.V.Hypervalent Iodine Chemistry:Preparation,Structure and Synthetic Applications of Polyvalent Iodine Compounds;John Wiley&Sons,Ltd.:New York,2014.(b)Wirth,T.Hypervalent Iodine Chemistry:Modern Developments in Organic Synthesis;Springer Science&Business Media:Berlin,2003.
    [10]Musher,J.I.Angew.Chem.Int.Ed.1969,8,54.
    [11]Perkins,C.W.;Martin,J.C.;Arduengo,A.J.;Lau,W.;Alegria,A.;Kochi,J.K.J.Am.Chem.Soc.1980,102,7753.
    [12]Ivanov,A.S.;Popov,I.A.;Boldyrev,A.I.;Zhdankin,V.V.Angew.Chem.Int.Ed.2014,53,9617.
    [13]Chen,Z.H.;Tu,Y.Q.;Zhang,S.Y.;Zhang,F.M.Org.Lett.2011,13,724.
    [14]Guo,S.;Liu,J.;Ma,D.Angew.Chem.Int.Ed.2015,54,1298.
    [15]Shi,H.;Tan,C.;Zhang,W.;Zhang,Z.;Long,R.;Gong,J.;Luo,T.;Yang,Z.J.Org.Chem.2016,81,751.
    [16]Iwata,M.;Kamijoh,Y.;Yamamoto,E.;Yamanaka,M.;Nagasawa,K.Org.Lett.2017,19,420.
    [17]Tian,G.;Fedoseev,P.;Van der Eycken,E.V.Chem.Eur.J.2017,23,5224.
    [18]Altermann,S.M.;Richardson,R.D.;Page,T.K.;Schmidt,R.K.;Holland,E.;Mohammed,U.;Paradine,S.M.;French,A.N.;Richter,C.;Bahar,A.M.;Witulski,B.;Wirth,T.Eur.J.Org.Chem.2008,5315.
    [19]Xie,J.H.;Zhou,Q.L.Acc.Chem.Res.2008,41,581.
    [20]Dohi,T.;Maruyama,A.;Takenaga,N.;Senami,K.;Minamistsuji,Y.;Fujioka,H.;Caemmerer,S.B.;Kita,Y.Angew.Chem.Int.Ed.2008,47,3787.
    [21]Yu,J.;Cui,J.;Hou,X.S.;Liu,S.S.;Gao,W.C.;Jiang,S.;Tian,J.;Zhang,C.Tetrahedron:Asymmetry 2011,22,2039.
    [22]Zhang,D.Y.;Xu,L.;Wu,H.;Gong,L.Z.Chem.Eur.J.2015,21,10314.
    [23]Banik,S.M.;Medley,J.W.;Jacobsen,E,N.Science 2016,353,51.
    [24]Zhang,X.;Cong,Y.;Lin,G.;Guo,X.;Cao,Y.;Lei,K.;Du,Y.Chin.J.Org.Chem.2016,36,2513.
    [25]Wang,Y.;Chen,C.;Peng,J.;Li,M.Angew.Chem.Int.Ed.2013,52,5323.
    [26]Su,X.;Chen,C.;Wang,Y.;Chen,J.;Lou,Z.;Li,M.Chem.Commun.2013,49,6752.
    [27]Zhang,X.;Yang,C.;Zhang-Negrerie,D.;Du,Y.Chem.-Eur.J.2015,21,5193.
    [28]Song,R.;Han,Z.;He,Q.;Fan,R.Org.Lett.2016,18,5328.
    [29]Wu,T.;Yin,G.;Liu,G.J.Am.Chem.Soc.2009,131,16354.
    [30]Cui,J.;Jia,Q.;Feng,R.Z.;Liu,S.S.;He,T.;Zhang,C.Org.Lett.2014,16,1442.
    [31]Han,Y.C.;Zhang,Y.D.;Jia,Q.;Cui,J.;Zhang,C.Org.Lett.2017,19,5300.
    [32]Li,X.T.;Gu,Q.S.;Dong,X.Y.;Meng,X.;Liu,X.Y.Angew.Chem.Int.Ed.2018,57,7668.
    [33]Agosta,W.C.Tetrahedron Lett.1965,6,2681.
    [34]Tian,J.;Gao,W.C.;Zhou,D.M.;Zhang,C.Org.Lett.2012,14,3020.
    [35]Zhang,C.;Liu,S.S.;Sun,B.;Tian,J.Org.Lett.2015,17,4106.
    [36]Yang,J.;Zhao,J.Sci.China:Chem.2018,61,97.
    [37]Liu,D.;Guo,Y.L.;Qu,J.;Zhang,C.Beilstein J.Org.Chem.2018,14,1112.
    [38]Ouyang,Q.;Yan,K.Q.;Zhu,Y.Z.;Zhang,C.H.;Liu,J.Z.;Chen,C.;Zheng,J.Y.Org.Lett.2012,14,2746.
    [39]He,M.;Swager,T.M.Chem.Mater.2016,28,8542.
    [40]Abrecht,S.;Adam,J.M.;Bromberger,U.;Diodone,R.;Fettes,A.;Fischer,R.;Goeckel,V.;Hildbrand,S.;Moine,G.;Weber,M.Org.Process Res.Dev.2011,15,503.
    [41]Purohit,V.C.;Allwein,S.P.;Bakale,R.P.Org.Lett.2013,15,1650.
    [42]Mullens,P.;Cleator,E.;McLaughlin,M.;Bishop,B.;Edwards,J.;Goodyear,A.;Andreani,T.;Jin,Y.;Kong,J.;Li,H.;Williams,M.;Zacuto,M.Org.Process Res.Dev.2016,20,1075.

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