Co-Catalyzed Radical Cycloaddition of [60]Fullerene with Active Dibromides: Selective Synthesis of Carbocycle-Fused Fullerene Monoadducts

被引:54
作者
Lu, Shirong [1 ]
Si, Weili [1 ]
Bao, Ming [2 ]
Yamamoto, Yoshinori [1 ,2 ]
Jin, Tienan [1 ]
机构
[1] Tohoku Univ, WPI Adv Inst Mat Res WPI AIMR, Sendai, Miyagi 9808577, Japan
[2] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China
关键词
CHEMISTRY; HYDROFULLERENES; DIMERIZATION; C-60; SULFONAMIDES; DERIVATIVES; CYCLIZATION; ACCEPTOR; WATER;
D O I
10.1021/ol401876n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and highly selective Co-catalyzed radical cycloaddition of [60]fullerene with active dibromides for the synthesis of three-, five-, six-, and seven-membered carbocycle-fused fullerene monoadducts has been reported. The controlled experiments unambiguously disclosed that the reaction proceeds through the formation of a fullerene monoradical as a key intermediate.
引用
收藏
页码:4030 / 4033
页数:4
相关论文
共 53 条
  • [11] An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1,3-dipolar cycloadditions
    Filippone, Salvatore
    Maroto, Enrique E.
    Martin-Domenech, Angel
    Suarez, Margarita
    Martin, Nazario
    [J]. NATURE CHEMISTRY, 2009, 1 (07) : 578 - 582
  • [12] Metal ion dependent fluorescence quenching in a crown ether bridged porphyrin-fullerene dyad
    Ghiggino, Kenneth P.
    Hutchison, James A.
    Islan, D. -M. Shatiqul
    Araki, Yasuyuki
    Ito, Osamu
    Langford, Steven J.
    Lau, Vei-Lin
    Takezaki, Makoto
    [J]. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2006, 5 (12) : 1150 - 1153
  • [13] New Concepts and Applications in the Macromolecular Chemistry of Fullerenes
    Giacalone, Francesco
    Martin, Nazario
    [J]. ADVANCED MATERIALS, 2010, 22 (38) : 4220 - 4248
  • [14] Biradical intermediate in the [2+2] photocycloaddition of dienes and alkenes to [60]fullerene
    Hatzimarinaki, M
    Roubelakis, MM
    Orfanopoulos, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) : 14182 - 14183
  • [15] Indene-C60 Bisadduct: A New Acceptor for High-Performance Polymer Solar Cells
    He, Youjun
    Chen, Hsiang-Yu
    Hou, Jianhui
    Li, Yongfang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) : 1377 - 1382
  • [16] Diels-Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60
    Hudhomme, Patrick
    [J]. COMPTES RENDUS CHIMIE, 2006, 9 (7-8) : 881 - 891
  • [17] Cobalt-catalyzed Heck-type reaction of alkyl halides with styrenes
    Ikeda, Y
    Nakamura, T
    Yorimitsu, H
    Oshima, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) : 6514 - 6515
  • [18] Functional fullerenes for organic photovoltaics
    Li, Chang-Zhi
    Yip, Hin-Lap
    Jen, Alex K. -Y.
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (10) : 4161 - 4177
  • [19] Cycloaddition reactions of hydrofullerenes with cyano-substituted alkenes under basic conditions
    Li, YJ
    Wang, GW
    Li, JX
    Liu, YC
    [J]. NEW JOURNAL OF CHEMISTRY, 2004, 28 (08) : 1043 - 1047
  • [20] Synthesis of [60]Fullerene-Fused Tetrahydronaphthalene and Indane Derivatives via a Pathway Switched by Aluminum Chloride
    Liu, Tong-Xin
    Li, Fa-Bao
    Wang, Guan-Wu
    [J]. ORGANIC LETTERS, 2011, 13 (22) : 6130 - 6133