Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp2) H activation and C(sp3)-H amination

被引:12
|
作者
Song, Liangliang [1 ]
Tian, Guilong [1 ]
Van der Eycken, Johan [2 ]
Van der Eycken, Erik V. [1 ,3 ]
机构
[1] Katholieke Univ Leuven, Dept Chem, LOMAC, Celestijnenlaan 200F, B-3001 Leuven, Belgium
[2] Univ Ghent, Dept Organ & Macromol Chem, Lab Organ & Bioorgan Synth, Krijgslaan 281 S4, B-9000 Ghent, Belgium
[3] Peoples Friendship Univ Russia, RUDN Univ, Miklukho Maklaya St 6, Moscow, Russia
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷
关键词
annulation; C-H activation; rhodium; acrylamide; heterocycles; CONCISE SYNTHESIS; DIRECTING GROUP; CAMPTOTHECIN; ALKYNES; AMIDE; FUNCTIONALIZATION; ALKENES;
D O I
10.3762/bjoc.15.52
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium(III)-catalyzed intramolecular oxidative annulation of O-substituted N-hydroxyacrylamides for the construction of indolizinones via sequential C(sp(2))-H activation and C(sp(3))-H amination has been developed. This approach shows excellent functional-group tolerance. The synthesized scaffold forms the core of many natural products with pharmacological relevance.
引用
收藏
页码:571 / 576
页数:6
相关论文
共 50 条
  • [1] Rhodium(iii)-catalyzed regioselective oxidative annulation of anilines and allylbenzenes via C(sp3)-H/C(sp2)-H bond cleavage
    Liu, Yunqi
    Yang, Yudong
    Wang, Chunxia
    Wang, Zhishuo
    You, Jingsong
    CHEMICAL COMMUNICATIONS, 2019, 55 (08) : 1068 - 1071
  • [2] Rhodium-Catalyzed Cascade Oxidative Annulation Leading to Substituted Naphtho[1,8-bc]pyrans by Sequential Cleavage of C(sp2)-H/C(sp3)-H and C(sp2)-H/O-H Bonds
    Tan, Xing
    Liu, Bingxian
    Li, Xiangyu
    Li, Bin
    Xu, Shansheng
    Song, Haibin
    Wang, Baiquan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (39) : 16163 - 16166
  • [3] Cyclometallated derivatives of rhodium(III).: Activation of C(sp3)-H vs. C(sp2)-H bonds
    Zucca, A
    Stoccoro, S
    Cinellu, MA
    Minghetti, G
    Manassero, M
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (19): : 3431 - 3437
  • [4] 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
  • [5] Intramolecular C(sp3)-H amination
    Jeffrey, Jenna L.
    Sarpong, Richmond
    CHEMICAL SCIENCE, 2013, 4 (11) : 4092 - 4106
  • [6] 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
  • [7] Rh(III)-Catalyzed Oxidative Annulation Leading to Substituted Indolizines by Cleavage of C(sp2)-H/C(sp3)-H Bonds
    Shen, Bingxue
    Li, Bin
    Wang, Baiquan
    ORGANIC LETTERS, 2016, 18 (12) : 2816 - 2819
  • [8] Iron-Catalyzed Intramolecular C(sp2)-H Amination
    Alt, Isabel T.
    Plietker, Bernd
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (04) : 1519 - 1522
  • [9] Pd-catalyzed regioselective activation of C(sp2)-H and C(sp3)-H bonds
    Ali, Wajid
    Oliver, Gwyndaf A.
    Werz, Daniel B.
    Maiti, Debabrata
    CHEMICAL SOCIETY REVIEWS, 2024, 53 (19) : 9904 - 9953
  • [10] Copper-Catalyzed Intramolecular C(sp3)-H and C(sp2)-H Amidation by Oxidative Cyclization
    Wang, Zhen
    Ni, Jizhi
    Kuninobu, Yoichiro
    Kanai, Motomu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (13) : 3496 - 3499