Cp*Co(III)-Catalyzed Regioselective Synthesis of Cyclopenta[b]carbazoles via Dual C(sp2)-H Functionalization of 1-(Pyridin-2-yl)-indoles with Diynes

被引:25
|
作者
Li, Qiuyun [1 ]
Wang, Yanwei [1 ]
Li, Bin [1 ]
Wang, Baiquan [1 ,2 ,3 ]
机构
[1] Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[2] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ACTIVATION; OXIDATIVE ANNULATION; COUPLING REACTIONS; INTERNAL ALKYNES; INDOLE SYNTHESIS; CYCLIZATION; ACCESS; ARENES; CARBOCYCLIZATION; INTERMEDIATE;
D O I
10.1021/acs.orglett.8b03438
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cp*Co(III)-catalyzed synthesis of cyclopenta [b-carbazoles from 1-(pyridin-2-yl)-indoles and diynes is developed. This reaction involves dual C-H activation of indoles and domino cyclizations with diynes and has excellent regioselectivity, high efficiency, a broad substrate scope, and tolerance for various functional groups. A series of cyclopenta[b]carbazole molecular scaffolds are obtained in good to excellent yields.
引用
收藏
页码:7884 / 7887
页数:4
相关论文
共 50 条
  • [21] Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp2)-H Functionalization
    Pandey, Ashok Kumar
    Han, Sang Hoon
    Mishra, Neeraj Kumar
    Kang, Dahye
    Lee, Suk Hun
    Chun, Rina
    Hong, Sungwoo
    Park, Jung Su
    Kim, In Su
    ACS CATALYSIS, 2018, 8 (01): : 742 - 746
  • [22] Three-Component Ru-Catalyzed Regioselective Alkylarylation of Vinylarenes via Meta-Selective C(sp2)-H Bond Functionalization
    Liu, Hong-Chao
    Gong, Xiao-Ping
    Wang, Yu-Zhao
    Niu, Zhi-Jie
    Yue, Heng
    Liu, Xue-Yuan
    Liang, Yong-Min
    ORGANIC LETTERS, 2022, 24 (16) : 3043 - 3047
  • [23] Co(II)-catalyzed regioselective clean and smooth synthesis of 2-(aryl/alkyl-thio)phenols via sp2 C-H bond activation
    Rostami, Abed
    Khakyzadeh, Vahid
    Zolfigol, Mohammad Ali
    Rostami, Amin
    MOLECULAR CATALYSIS, 2018, 452 : 260 - 263
  • [24] Removal of the Pyridine Directing Group from α-Substituted N-(Pyridin-2-yl)piperidines Obtained via Directed Ru-Catalyzed sp3 C-H Functionalization
    Smout, Veerle
    Peschiulli, Aldo
    Verbeeck, Stefan
    Mitchell, Emily A.
    Herrebout, Wouter
    Bultinck, Patrick
    Vande Velde, Christophe M. L.
    Berthelot, Didier
    Meerpoel, Lieven
    Maes, Bert U. W.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19): : 9803 - 9814
  • [25] A Practical Synthesis of the TGFβRI Inhibitor N-(4-(3-(6-(Difluoromethyl)pyridin-2-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)pyridin-2-yl)acetamide via One-Pot Sequential Sonogashira and Cacchi Reactions Catalyzed by Pd(OAc)2/BINAP
    Li, Jianqing
    Smith, Daniel
    Krishnananthan, Subramaniam
    Mathur, Arvind
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2020, 24 (03) : 454 - 458
  • [26] Synthesis of Indolyl-Tethered Spiro[cyclobutane-1,1′-indenes] through Cascade Reactions of 1-(Pyridin-2-yl)-1H-indoles with Alkynyl Cyclobutanols
    Xu, Yuanshuang
    Yu, Caiyun
    Zhang, Xinying
    Fan, Xuesen
    ORGANIC LETTERS, 2021, 23 (21) : 8510 - 8515
  • [27] Direct Ortho Arylation of 9-(Pyridin-2-yl)-9H-carbazoles Bearing a Removable Directing Group via Palladium(II)-Catalyzed C-H Bond Activation
    Chu, Jean-Ho
    Wu, Chung-Chiu
    Chang, Deng-Hsiang
    Lee, Ya-Ming
    Wu, Ming-Jung
    ORGANOMETALLICS, 2013, 32 (01) : 272 - 282
  • [28] I2-Induced Metal-Free C(sp2)-H Functionalization of Indoles via One-Pot and Two-Step Reaction with 1-(2-Hydroxyphenyl)-propargyl Alcohols: Access to 3-(Benzofuran-3-yl)-1H-indoles
    Zhu, Yang
    Deng, Guisheng
    JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [29] Copper-Catalyzed Tandem Aerobic Oxidative Cyclization for the Synthesis of Polysubstituted Quinolines via C(sp3)/C(sp2)-H Bond Functionalization
    Pang, Xiaobo
    Wu, Mingzhong
    Ni, Jixiang
    Zhang, Fuming
    Lan, Jingfeng
    Chen, Baohua
    Yan, Rulong
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19): : 10110 - 10120
  • [30] Palladium-Catalyzed Synthesis of 2-(1-Isochromen-3-yl)acetaldehydes via Carboxyl-Directed C(sp2)-H Alkylation/Annulation
    Wang, Yue
    Yang, Xuyan
    Liu, Tianyu
    Li, Tuanjie
    Zhang, Kai
    Yao, Changsheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (11) : 3556 - 3563