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

被引：17
|
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
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 18期
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
    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
    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
    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
    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.
    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
    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
    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
    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.
    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
    ORGANIC LETTERS, 2017, 19 (02) : 396 - 399
12345