Rh(III)-Catalyzed Oxidative Annulation Leading to Substituted Indolizines by Cleavage of C(sp2)-H/C(sp3)-H Bonds

被引:68
|
作者
Shen, Bingxue [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; PYRROLE-CONTAINING HETEROCYCLES; HIGHLY EFFICIENT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; PYRIDINIUM YLIDES; DIAZO-COMPOUNDS; CATALYZED CYCLOISOMERIZATION; FUNCTIONALIZED INDOLIZINES; INTERMOLECULAR AMIDATION; ROOM-TEMPERATURE;
D O I
10.1021/acs.orglett.6b01181
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(III)-catalyzed oxidative annulation reactions of pyridinium trifluoromethanesulfonate salts with alkynes leading to substituted indolizines by cleavage of C(sp(2))-H/C(sp(3))-H bonds are developed. The starting materials are readily available, and the reactions have a broad substrate scope. This reaction overcomes some drawbacks of the previous indolizine synthetic methods and provides a new efficient route to indolizine derivatives.
引用
收藏
页码:2816 / 2819
页数:4
相关论文
共 50 条
  • [31] Iron- Catalyzed C( sp2)-H and C( sp3) -H Arylation by Triazole Assistance
    Gu, Qing
    Al Mamari, Hamad H.
    Graczyk, Karolina
    Diers, Emelyne
    Ackermann, Lutz
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (15) : 3868 - 3871
  • [32] Mechanism of Nickel(II)-Catalyzed Oxidative C(sp2)-H/C(sp3)-H Coupling of Benzamides and Toluene Derivatives
    Xu, Zheng-Yang
    Jiang, Yuan-Ye
    Yu, Hai-Zhu
    Fu, Yao
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (11) : 2479 - 2483
  • [33] Iron-Catalyzed Directed C(sp2)-H and C(sp3)-H Functionalization with Trimethylaluminum
    Shang, Rui
    Ilies, Laurean
    Nakamura, Eiichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (24) : 7660 - 7663
  • [34] Scalable Electrochemical Dehydrogenative Lactonization of C(sp2/sp3)-H Bonds
    Zhang, Sheng
    Li, Lijun
    Wang, Huiqiao
    Li, Qian
    Liu, Wenmin
    Xu, Kun
    Zeng, Chengchu
    ORGANIC LETTERS, 2018, 20 (01) : 252 - 255
  • [35] Palladium-Catalyzed Direct Acyloxylation of C(sp2)-H and C(sp3)-H Bonds under the Assistance of Oxalyl Amide
    Zheng, Yongxiang
    Han, Jian
    Huang, Zhibin
    Shi, Daqing
    Zhao, Yingsheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (08) : 2066 - 2072
  • [36] Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)-H and C(sp3)-H Bonds at δ- and ε-Positions
    Wang, Chao
    Chen, Changpeng
    Zhang, Jingyu
    Han, Jian
    Wang, Qian
    Guo, Kun
    Liu, Pei
    Guan, Mingyu
    Yao, Yingming
    Zhao, Yingsheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) : 9884 - 9888
  • [37] Multicomponent double Mannich alkylamination involving C(sp2)-H and benzylic C(sp3)-H bonds
    Lai, Zhencheng
    Wu, Rongkai
    Li, Jiaming
    Chen, Xing
    Zeng, Linwei
    Wang, Xi
    Guo, Jingjing
    Zhao, Zujin
    Sajiki, Hironao
    Cui, Sunliang
    NATURE COMMUNICATIONS, 2022, 13 (01)
  • [38] Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups
    Rouquet, Guy
    Chatani, Naoto
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) : 11726 - 11743
  • [39] Catalytic Cleavage of C(sp2)-C(sp2 ) Bonds with Rh-Carbynoids
    Wang, Zhaofeng
    Jiang, Liyin
    Sarro, Pau
    Suero, Marcos G.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (39) : 15509 - 15514
  • [40] Multicomponent double Mannich alkylamination involving C(sp2)–H and benzylic C(sp3)–H bonds
    Zhencheng Lai
    Rongkai Wu
    Jiaming Li
    Xing Chen
    Linwei Zeng
    Xi Wang
    Jingjing Guo
    Zujin Zhao
    Hironao Sajiki
    Sunliang Cui
    Nature Communications, 13