Cu(I)-Catalyzed Synthesis of [60]Fullerene-Fused Lactams and Further Electrochemical Functionalization

被引:32
作者
Liu, Zhan [1 ,2 ]
Yin, Zheng-Chun [1 ,2 ]
Lu, Wen-Qiang [1 ,2 ]
Niu, Chuang [1 ,2 ]
Chen, Muqing [4 ,5 ]
Yang, Shangfeng [4 ,5 ]
Wang, Guan-Wu [1 ,2 ,3 ]
机构
[1] Univ Sci & Technol China, CAS Key Lab Soft Matter Chem, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[4] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Mat Energy Convers, Hefei 230026, Anhui, Peoples R China
[5] Univ Sci & Technol China, Dept Mat Sci & Engn, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
REGIOSELECTIVE ELECTROSYNTHESIS; C-60;
D O I
10.1021/acs.orglett.1c01269
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient Cu(I)-catalyzed radical heteroannulation reaction of [60]fullerene (C-60) with alpha-bromo acetamides has been disclosed for the direct synthesis of diverse C-60-fused lactams. Furthermore, the formed C-60-fused lactams can be served as a versatile platform for further electrochemical functionalization to prepare 1,2-, 1,4-, 1,2,3,16-, and 1,4,9,25-adducts of C-60. In addition, a representative fullerene product has been applied as an overcoating layer of the electron-transporting layer in n-type perovskite solar cell.
引用
收藏
页码:4051 / 4056
页数:6
相关论文
共 44 条
  • [1] Silver(I)-mediated three-component annulation reaction of [60]fullerene, sulfonylhydrazones, and nitriles: leading to diverse disubstituted [60]fullerene-fused dihydropyrroles
    Chao, Di
    Liu, Tong-Xin
    Ma, Nana
    Zhang, Pengling
    Fu, Zheng
    Ma, Jinliang
    Liu, Qingfeng
    Zhang, Fengjin
    Zhang, Zhiguo
    Zhang, Guisheng
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (05) : 982 - 985
  • [2] Base-Promoted Consecutive Enolate Addition Reaction of [60]Fullerene with Ketones
    Chen, Si
    Li, Zong-Jun
    Li, Shu-Hui
    Gao, Xiang
    [J]. ORGANIC LETTERS, 2015, 17 (21) : 5192 - 5195
  • [3] One-pot sequential synthesis of acetoxylated [60]fullerene derivatives
    Chen, ZX
    Wang, GW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) : 2380 - 2383
  • [4] Annulation of Benzamides with [60]Fullerene through Palladium(II)-Catalyzed C-H Bond Activation
    Chuang, Shih-Ching
    Rajeshkumar, Venkatachalam
    Cheng, Chun-An
    Deng, Jie-Cheng
    Wang, Guan-Wu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06) : 1599 - 1604
  • [5] Synthesis and Functionalization of [60]Fullerene-Fused Imidazolines
    He, Cheng-Lin
    Liu, Rui
    Li, Dan-Dan
    Zhu, San-E
    Wang, Guan-Wu
    [J]. ORGANIC LETTERS, 2013, 15 (07) : 1532 - 1535
  • [6] Reductive Benzylation of C60 Imidazoline with a Bulky Addend
    Hou, Hui-Lei
    Li, Zong-Jun
    Gao, Xiang
    [J]. ORGANIC LETTERS, 2014, 16 (03) : 712 - 715
  • [7] Palladium-catalyzed synthesis of [60]fullerene-fused furochromenones and further electrochemical functionalization
    Hussain, Majid
    Niu, Chuang
    Wang, Guan-Wu
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (10) : 1249 - 1254
  • [8] Palladium-Catalyzed Heteroannulation of Indole-1-carboxamides with [60]Fullerene and Subsequent Electrochemical Transformations
    Hussain, Majid
    Chen, Muqing
    Yang, Shangfeng
    Wang, Guan-Wu
    [J]. ORGANIC LETTERS, 2019, 21 (21) : 8568 - 8571
  • [9] Functionalization of fullerene materials toward applications in perovskite solar cells
    Jia, Lingbo
    Chen, Muqing
    Yang, Shangfeng
    [J]. MATERIALS CHEMISTRY FRONTIERS, 2020, 4 (08) : 2256 - 2282
  • [10] Linear free energy relation of methanofullerene C-61-substituents with cyclic voltammetry: Strong electron withdrawal anomaly
    KeshavarzK, M
    Knight, B
    Haddon, RC
    Wudl, F
    [J]. TETRAHEDRON, 1996, 52 (14) : 5149 - 5159