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 50 条
  • [1] Palladium-catalyzed synthesis of [60]fullerene-fused furochromenones and further electrochemical functionalization
    Hussain, Majid
    Niu, Chuang
    Wang, Guan-Wu
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (10) : 1249 - 1254
  • [2] Synthesis and Functionalization of [60]Fullerene-Fused Imidazolines
    He, Cheng-Lin
    Liu, Rui
    Li, Dan-Dan
    Zhu, San-E
    Wang, Guan-Wu
    ORGANIC LETTERS, 2013, 15 (07) : 1532 - 1535
  • [3] Copper-Catalyzed N-Heteroannulation of [60]Fullerene with Aryl Sulfonamides and Paraformaldehyde: Synthesis and Functionalization of [60]Fullerene-Fused Imidazolidines
    Yin, Zheng-Chun
    Hussain, Majid
    Ye, Shi-Qi
    Lu, Yong-Ming
    Niu, Chuang
    Zhang, Qian-Wen
    Li, Jian-Feng
    Wang, Guan-Wu
    ORGANIC LETTERS, 2025, 27 (11) : 2741 - 2746
  • [4] A retro Baeyer-Villiger reaction: electrochemical reduction of [60]fullerene-fused lactones to [60]fullerene-fused ketones
    Niu, Chuang
    Zhou, Dian-Bing
    Yang, Yong
    Yin, Zheng-Chun
    Wang, Guan-Wu
    CHEMICAL SCIENCE, 2019, 10 (10) : 3012 - 3017
  • [5] Regioselective Electrochemical Hydroalkylations of [60]Fullerene-Fused Furochromenone
    Yin, Zheng-Chun
    Niu, Chuang
    Li, Mingjie
    Liu, Wen-Rui
    Wang, Guan-Wu
    CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (07) : 769 - 775
  • [6] Synthesis of [60]fullerene-fused thiolactams and thiaimidates
    Li, Jia-Xing
    Wang, Guan-Wu
    TETRAHEDRON LETTERS, 2012, 53 (13) : 1610 - 1612
  • [7] Progress in Electrochemical Reactions of [60]Fullerene-Fused Heterocycles
    Niu, Chuang
    Wang, Guanwu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (11) : 3633 - 3645
  • [8] Palladium-catalyzed synthesis of [60]fullerene-fused benzofurans via heteroannulation of phenols
    Li, Fei
    Wang, Jun-Jie
    Wang, Guan-Wu
    CHEMICAL COMMUNICATIONS, 2017, 53 (11) : 1852 - 1855
  • [9] Synthesis of [60]Fullerene-Fused Allylbenzofurans via Palladium-Catalyzed Migration Reaction
    Liu, Tong-Xin
    Yang, Panting
    Ma, Nana
    Li, Xiaojun
    Wang, Xin
    Ma, Jinliang
    Zhang, Guisheng
    CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (14): : 1733 - 1739
  • [10] Synthesis of [60]fullerene-fused dihydrobenzooxazepines via the palladium-catalyzed oxime-directed C-H bond activation and subsequent electrochemical functionalization
    Wang, Chen
    Liu, Zhan
    Yin, Zheng-Chun
    Wang, Guan-Wu
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17) : 2518 - 2525