Pd-Catalyzed Sequential Arylation of 7-Azaindoles: Aggregate-Induced Emission of Tetra-Aryl 7-Azaindoles

被引：18
|
作者：
Cardoza, Savio [1 ]
Das, Parthasarathi [2 ]
Tandon, Vibha [1 ]
机构：
[1] Jawaharlal Nehru Univ, Special Ctr Mol Med, New Delhi 110067, India
[2] Indian Inst Technol, Indian Sch Mines, Dept Chem, Dhanbad 826004, Jharkhand, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期
关键词：
C-H ARYLATION; STATE PROTON-TRANSFER; DIRECT C-2 ARYLATION; PHOTOPHYSICAL PROPERTIES; INDOLES; DERIVATIVES; PYRROLES; ACCESS; SUBSTITUENTS; ALKYNYLATION;
D O I：
10.1021/acs.joc.9b02187
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pd-catalyzed synthesis of multi-aryl 7-azaindoles using sequential arylation of 5-bromo-6-chloro-3-iodo-1-methyl-1H-pyrrolo[2,3-b] pyridine is established. Four diverse aryl groups are installed in a chemo-selective fashion providing a general method to synthesize sterically encumbered compounds and extended 7-azaindoles in 48-95% yields. Three-selective sequential arylations at C-3, C-5, and C-6 via Suzuki-Miyaura cross-coupling followed by direct C-2 arylation using a Pd catalyst and AgOTf as an additive are highlights of the present work. Interestingly, the tetra-aryl 7-azaindoles showed aggregate-induced emission (AIE) making it potentially useful as fluorophores in OLEDs, sensors, and bio-imaging tools.
引用
收藏
页码：14015 / 14029
页数：15
相关论文
共 35 条
  • [1] Palladium-catalyzed functionalization of 5-and 7-azaindoles
    Chi, SM
    Choi, JK
    Yum, EK
    Chi, DY
    TETRAHEDRON LETTERS, 2000, 41 (06) : 919 - 922
  • [2] Rhodium-catalyzed selective oxidative coupling of 7-azaindoles
    Li, Shuai-Shuai
    Wang, Cheng-Qi
    Li, Wei-Huan
    Zhang, Xiao-Mei
    Dong, Lin
    TETRAHEDRON, 2016, 72 (20) : 2581 - 2586
  • [3] Palladium-catalyzed regioselective C-2 arylation of 7-azaindoles, indoles, and pyrroles with arenes
    Laha, Joydev K.
    Bhimpuria, Rohan A.
    Prajapati, Dilip V.
    Dayal, Neetu
    Sharma, Shubhra
    CHEMICAL COMMUNICATIONS, 2016, 52 (23) : 4329 - 4332
  • [4] Direct C-2 Arylation of 7-Azaindoles: Chemoselective Access to Multiarylated Derivatives
    Kannaboina, Prakash
    Anilkumar, K.
    Aravinda, S.
    Vishwakarma, Ram A.
    Das, Parthasarathi
    ORGANIC LETTERS, 2013, 15 (22) : 5718 - 5721
  • [5] Regioselective Ir(III)-catalyzed C-H alkynylation directed by 7-azaindoles
    Liu, Bin
    Wang, Xin
    Ge, Zemei
    Li, Runtao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (10) : 2944 - 2949
  • [6] Palladium-Catalyzed Cross-Coupling between 7-Azaindoles and Reformatsky Reagents
    Barl, Nadja M.
    Malakhov, Vladimir
    Mathes, Christian
    Lustenberger, Philipp
    Knochel, Paul
    SYNTHESIS-STUTTGART, 2015, 47 (05): : 692 - 700
  • [7] Rhodium-Catalyzed Hydrogen-Releasing ortho-Alkenylation of 7-Azaindoles
    Li, Wei-Huan
    Wu, Lin
    Li, Shuai-Shuai
    Liu, Chen-Fei
    Zhang, Guo-Tai
    Dong, Lin
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (50) : 17926 - 17929
  • [8] Ru(II)-Catalyzed Difluoromethylations of 7-Azaindoles: Access to Novel Fluoro-7-Azaindole Derivatives
    Zhu, Yan-Ying
    Xu, Hui-Bei
    Zhang, Jing
    Luo, Yi
    Dong, Lin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (06) : 1410 - 1413
  • [9] CuI/DMAP-Catalyzed Oxidative Alkynylation of 7-Azaindoles: Synthetic Scope and Mechanistic Studies
    Talukdar, Vishal
    Mondal, Krishanu
    Dhaked, Devendra Kumar
    Das, Parthasarathi
    CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (06)
  • [10] Rhodium(III)-catalyzed C-C coupling of 7-azaindoles with vinyl acetates and allyl acetates
    Li, Shuai-Shuai
    Wang, Cheng-Qi
    Lin, Hui
    Zhang, Xiao-Mei
    Dong, Lin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (01) : 229 - 237
1234