Synthesis of Diverse 1,4-(Azaindole)[60]fullerenes via Transition-Metal Free Three-Component Coupling Reaction of Azaindoles, C60, and Bromoalkanes/Triphenylamines

被引:3
作者
Huang, Xinmin [1 ,2 ,3 ,4 ,5 ]
Liu, Zi-Zheng [1 ,2 ,3 ,4 ]
Cheng, Jia-Qi [1 ,2 ,3 ,4 ]
Cao, Cheng-Yu [1 ,2 ,3 ,4 ]
Li, Peng-Cheng [1 ,2 ,3 ,4 ]
Xuan, Jun [1 ,2 ,3 ,4 ]
Li, Fei [1 ,2 ,3 ,4 ,5 ]
机构
[1] Anhui Univ, Dept Chem, Hefei 230601, Anhui, Peoples R China
[2] Anhui Univ, Key Lab Struct & Funct Regulat Hybrid Mat, Minist Educ, Hefei 230601, Anhui, Peoples R China
[3] Anhui Prov Key Lab Chem Inorgan Organ Hybrid Funct, Hefei 230601, Anhui, Peoples R China
[4] Key Lab Funct Inorgan Mat Anhui Prov, Hefei 230601, Anhui, Peoples R China
[5] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
Azaindoles; Fullerenes; 1,4-(Azaindole)[60]fullerenes; Transition-metal free; Cross-coupling; ONE-POT; FULLERENE CHEMISTRY; SELECTIVE SYNTHESIS; REGIOSELECTIVITY; TETRAALLYLATION; CYCLOADDITION; DIMERIZATION; DERIVATIVES; STRATEGY; INDOLES;
D O I
10.1002/cjoc.202300292
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A transition-metal free three-component coupling reaction of azaindoles, C60, and bromoalkanes/triphenylamines has been developed to provide an efficient access to diverse azaindole functionalized 1,4-C60 adducts. This protocol exhibits low cost, operational simplicity, wide substrate scope, and mild and convenient conditions.
引用
收藏
页码:2975 / 2980
页数:6
相关论文
共 18 条
  • [1] One-Pot Synthesis of Diverse 1,4-[60]Fullerephenols via Three-Component Umpolung Cascade Coupling of Phenols, C60, and Nucleophiles
    Zhang, Jun-Xiang
    Wu, Yuan-Ze
    Chen, Dong-Mei
    Xuan, Jun
    Li, Fei
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (35)
  • [2] Synthesis of diverse unsymmetric 1,4-adducts via a three-component coupling reaction of malonate derivatives, [60]fullerene and electrophiles/nucleophiles
    Zhang, Da-Kang
    Ma, Wen-Bin
    Wei, Shuo-Yuan
    Chen, De-Yun
    Hu, Xiao
    Xuan, Jun
    Li, Fei
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (07) : 1626 - 1632
  • [3] KOtBu-Mediated, Three-Component Coupling Reaction of Indoles, [60]Fullerene, and Haloalkanes: One-Pot, Transition-Metal-Free Synthesis of Various 1,4-(3-Indole)(organo)[60]fullerenes
    Li, Fei
    Wang, Lianghui
    Wang, Junjie
    Peng, Dan
    Zhao, Yuqi
    Li, Shengli
    Zhou, Hongping
    Wu, Jieying
    Tian, Xiaohe
    Tian, Yupeng
    ORGANIC LETTERS, 2017, 19 (05) : 1192 - 1195
  • [4] Potassium salt promoted regioselective three-component coupling synthesis of 1,4-asymmetrical [60]fullerene bisadducts with superior electron transport properties
    Li, Fei
    Shang, Yanbo
    Niu, Chuang
    Li, Chao
    Huang, Xinmin
    Xu, Guoyong
    Xuan, Jun
    Zhou, Hongping
    Yang, Shangfeng
    CHEMICAL COMMUNICATIONS, 2020, 56 (66) : 9513 - 9516
  • [5] Three-component coupling reaction of the C60 fullerene, indole and propargyl bromide: a theoretical study
    Soleymani, Mousa
    Khavidaki, Hossein Dashti
    Hosseini, Mehdi
    REACTION KINETICS MECHANISMS AND CATALYSIS, 2020, 130 (01) : 75 - 90
  • [6] Three-component coupling reaction of the C60 fullerene, indole and propargyl bromide: a theoretical study
    Mousa Soleymani
    Hossein Dashti Khavidaki
    Mehdi Hosseini
    Reaction Kinetics, Mechanisms and Catalysis, 2020, 130 : 75 - 90
  • [7] KOtBu-Promoted C4 Selective Coupling Reaction of Phenols and [60]Fullerene: One-Pot Synthesis of 4-[60]Fullerephenols under Transition-Metal-Free Conditions
    Li, Fei
    Xuan, Jun
    Zhang, Shu
    Liu, Boxiang
    Yan, Jianxiao
    Liu, Kaiqing
    Liu, Dandan
    Zhang, Qiong
    Zhou, Hongping
    Wu, Jieying
    Tian, Yupeng
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10) : 5431 - 5437
  • [8] KOtBu-Mediated Coupling of Indoles and [60]Fullerene: Transition-Metal-Free and General Synthesis of 1,2-(3-Indole)(hydro)[60]fullerenes
    Li, Fei
    Elhussin, Imad Elddin Haj
    Li, Shengli
    Zhou, Hongping
    Wu, Jieying
    Tian, Yupeng
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) : 10605 - 10610
  • [9] Metal-Free-Catalyzed Three-Component [2+2+2] Annulation Reaction of [60]Fullerene, Ketones, and Indoles: Access to Diverse [60]Fullerene-Fused 1,2-Tetrahydrocarbazoles
    Ma, Jinliang
    Liu, Tong-Xin
    Zhang, Pengling
    Zhao, Xuna
    Zhang, Guisheng
    ORGANIC LETTERS, 2021, 23 (05) : 1775 - 1781
  • [10] Transition-Metal-Free Synthesis of Unsymmetrical Disulfides via Three-Component Reaction of Thiosulfonates, Thiourea and Alkyl halides
    Wang, Dungai
    He, Quan
    Shi, Keqiang
    Xiong, Mingteng
    Zhou, Yifeng
    Pan, Yuanjiang
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (11) : 2767 - 2772