Dual C(sp3)-H and C(sp2)-H Activation of 8-Methylquinoline N-Oxides: A Route to Access C7-H Bond

被引:1
|
作者
Mandal, Santu [1 ]
Barman, Madhab [1 ]
Debnath, Bijoy [1 ]
Punniyamurthy, Tharmalingam [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India
关键词
C-H ACTIVATION; QUINOLINE; SITE; FUNCTIONALIZATION; PD; QUINAZOLINE; DERIVATIVES; ALKYLATION;
D O I
10.1021/acs.orglett.4c02584
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd(II)-catalyzed regioselective dual C(sp(3))-H/C7(sp(2))-H activation and annulation of 8-methylquinoline N-oxides with maleimide has been accomplished. The use of N-oxide as a weak directing group under Pd(II)-complex catalysis activates the initial C(sp(3))-H and triggers a relayed, second C7(sp(2))-H activation. The dual C-H bond activation, [3 + 2]-annulation, facile introduction and removal of the directing group, substrate scope, and functional group diversity are the important practical features.
引用
收藏
页码:7560 / 7564
页数:5
相关论文
共 50 条
  • [1] Cp*CoIII-Catalyzed C(sp3)-H Bond Amidation of 8-Methylquinoline
    Barsu, Nagaraju
    Rahman, Md Atiur
    Sen, Malay
    Sundararaju, Basker
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (27) : 9135 - 9138
  • [2] Palladium-Catalyzed Annulations via Sequential C-H Activations of C(sp2)-H/C(sp3)-H or C(sp3)-H/C(sp3)-H Bonds
    Wei, Wan-Xu
    Czajkowski, Mateusz
    Kuang, Yangjin
    Nguyen, Tu-Anh V.
    Qin, Bo
    Tomanik, Martin
    ACS CATALYSIS, 2024, 14 (09) : 6535 - 6546
  • [3] Modular synthesis of dihydro-isoquinolines: palladium-catalyzed sequential C(sp2)-H and C(sp3)-H bond activation
    Liu, Weidong
    Yu, Qingzhen
    Hu, Le'an
    Chen, Zenghua
    Huang, Jianhui
    CHEMICAL SCIENCE, 2015, 6 (10) : 5768 - 5772
  • [4] Cp*Co(III)-Catalyzed C(sp3)-H Bond Activation: A Highly Stereoselective and Regioselective Alkenylation of 8-Methylquinoline with Alkynes
    Sen, Malay
    Emayavaramban, Balakumar
    Barsu, Nagaraju
    Premkumar, J. Richard
    Sundararaju, Basker
    ACS CATALYSIS, 2016, 6 (05): : 2792 - 2796
  • [5] Transition-Metal-Catalyzed Acyloxylation: Activation of C(sp2)-H and C(sp3)-H Bonds
    Moghimi, Setareh
    Mahdavi, Mohammad
    Shafiee, Abbas
    Foroumadi, Alireza
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (20) : 3282 - 3299
  • [6] Cooperative C(sp3)-H and C(sp2)-H Activation of 2-Ethylpyridines by Copper and Rhodium: A Route toward Quinolizinium Salts
    Luo, Ching-Zong
    Gandeepan, Parthasarathy
    Wu, Yun-Ching
    Tsai, Chia-Hung
    Cheng, Chien-Hong
    ACS CATALYSIS, 2015, 5 (08): : 4837 - 4841
  • [7] Visible-Light-Promoted Radical Cross-Dehydrogenative Coupling of C(sp3)-H/C(sp3)-H and C(sp3)-H/C(sp2)-H via Intermolecular HAT
    Xie, Xinpeng
    Qiao, Kaikai
    Shao, Bing-ru
    Jiang, Wenfeng
    Shi, Lei
    ORGANIC LETTERS, 2023, 25 (23) : 4264 - 4269
  • [8] Photochemical C-H bond coupling for (hetero)aryl C(sp2)-C(sp3) bond construction
    Zhao, Yating
    Xia, Wujiong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (20) : 4951 - 4963
  • [9] Ruthenium(II) Biscarboxylate-Catalyzed Borylations of C(sp2)-H and C(sp3)-H Bonds
    De Sarkar, Suman
    Kumar, N. Y. Phani
    Ackermann, Lutz
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (01) : 84 - 87
  • [10] Redox-Neutral Rhodium-Catalyzed C-H Functionalization of Arylamine N-Oxides with Diazo Compounds: Primary C(sp3)-H/C(sp2)-H Activation and Oxygen-Atom Transfer
    Zhou, Bing
    Chen, Zhaoqiang
    Yang, Yaxi
    Ai, Wen
    Tang, Huanyu
    Wu, Yunxiang
    Zhu, Weiliang
    Li, Yuanchao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (41) : 12121 - 12126