An Articulate Oxidative Transition-Metal-Free Homocoupling of Imidazo Heterocycles through C(sp2)-C(sp2) Bond Formation

被引:16
|
作者
Shakoor, S. M. Abdul [1 ]
Mandal, Sanjay K. [2 ]
Sakhuja, Rajeev [1 ]
机构
[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India
[2] Indian Inst Sci Educ & Res Mohali, Dept Chem Sci, Sect 81,Manuali PO, Sas Nagar 140306, Punjab, India
关键词
C-H activation; Hypervalent compounds; Homocoupling; Nitrogen heterocycles; Iodine reagents; C-H ACTIVATION; COUPLING REACTIONS; AMBIENT-TEMPERATURE; METHYLENE SOURCE; IODINE REAGENTS; IMIDAZOHETEROCYCLES; FUNCTIONALIZATION; DERIVATIVES; AMINATION; ARENES;
D O I
10.1002/ejoc.201700238
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct oxidative homocoupling of 2-arylimidazo heterocycles was achieved by using a phenyliodine diacetate-mediated BF3<bold>OEt</bold>2-accelerated protocol at room temperature. A series of biimidazo heterocycles were synthesized under ambient conditions without prior activation of the C(sp(2))-H bond. The desired biimidazo heterocycles were also obtained by using catalytic amounts of iodobenzene and m-CPBA/AcOH in an organocatalytic fashion.
引用
收藏
页码:2596 / 2602
页数:7
相关论文
共 50 条
  • [1] Recent Progress in Amination Enabled by Transition-Metal-Free C(sp2)-O/C(sp2)-S Bond Cleavage Strategy
    Lia, Shen-Huan
    Longa, Cheng-Yu
    Yang, Xin-Ge
    Wang, Xue-Qiang
    [J]. SYNTHESIS-STUTTGART, 2021, 53 (20): : 3716 - 3724
  • [2] Recent Advances in the C(sp2)-S Bond Formation Reactions by Transition Metal-Free C(sp2)-H Functionalization
    Liu, Yunyun
    Xiong, Jin
    Wei, Li
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (07) : 1667 - 1680
  • [3] Progress in C-N Bond Formation Involving C(sp2)-H Bond through Transition-Metal-Free Radical Reactions
    Wu, Yan
    Chen, Jinvang
    Li, Qiang
    Wei, Wenting
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (03) : 589 - 597
  • [4] Transition-Metal-Free C(sp2)-C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters
    Wu, Kai
    Wu, Liang-Liang
    Zhou, Cong-Ying
    Che, Chi-Ming
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (37) : 16202 - 16208
  • [5] Copper-Catalyzed C(sp2)-C(sp2) Bond Formation via Single C(sp2)-H Activation
    Parmar, Himanshu V.
    Adodariya, Yash J.
    Patel, Unnati P.
    Shrivastav, Pranav S.
    Maru, Jayesh J.
    [J]. CHEMISTRYSELECT, 2024, 9 (02):
  • [6] Transition-metal free C(sp2)-C(sp2) bond formation: arylation of 4-aminocoumarins using arynes as an aryl source
    Sharma, Abhilash
    Gogoi, Pranjal
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (40) : 9014 - 9025
  • [7] Transition-metal-free electrochemical oxidative C(sp2)-H trifluoromethylation of aryl aldehyde hydrazones
    Shi, Yuan
    Wang, Kai
    Ding, Yuxin
    Xie, Yuanyuan
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (47) : 9362 - 9367
  • [8] Transition-Metal-Free Synthesis of N-Substituted Phenanthridinones and Spiro-isoindolinones: C(sp2)-N and C(sp2)-O Coupling through Radical Pathway
    Verma, Ajay
    Banjara, Lal Singh
    Meena, Rahul
    Kumar, Sangit
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (01) : 105 - 110
  • [9] Nickel/α-diimine catalysts in C (sp2)-C (sp2) homocoupling: An underestimated and versatile ligand family
    Kudakina, Vera A.
    Asachenko, Andrey F.
    Valaeva, Valentina N.
    Lebedev, Artyom Y.
    Razavi, Abbaz
    Mladentsev, Dmitry Y.
    Uborsky, Dmitry V.
    Voskoboynikov, Alexander Z.
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2024, 38 (04)
  • [10] Transition-Metal-Free Lactonization of sp2 C-H Bonds with CO2
    Zhang, Zhen
    Ju, Tao
    Miao, Meng
    Han, Jie-Lian
    Zhang, Yi-Han
    Zhu, Xing-Yong
    Ye, Jian-Heng
    Yu, Da-Gang
    Zhi, Yong-Gang
    [J]. ORGANIC LETTERS, 2017, 19 (02) : 396 - 399