Hydroxoiridium-Catalyzed sp3 C-H Alkylation of Indoline Derivatives with Terminal Alkenes

被引：11
|
作者：
Nakamura, Ikumi [1 ]
Yamauchi, Daisuke [2 ]
Nishimura, Takahiro [1 ]
机构：
[1] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi Ku, Osaka 5588585, Japan
[2] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 07期
关键词：
alkenes; C-H activation; indolines; iridium; synthetic methods; C(SP(3))-H ALPHA-ALKYLATION; BOND ACTIVATION; VINYL ETHERS; INTERMOLECULAR HYDROAMINOALKYLATION; SELECTIVE HYDROARYLATION; COUPLING REACTION; FUNCTIONALIZATION; ADJACENT; NITROGEN; MECHANISM;
D O I：
10.1002/ajoc.201800189
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Direct alkylation of a secondary sp(3) C-H bond of indoline derivatives having a urea moiety with terminal alkenes proceeded in the presence of a hydroxoiridium/1,5-cyclooctadiene catalyst, which generated an amidoiridium intermediate by reaction with a urea N-H moiety of the indolines, giving the linear addition products in high yields.
引用
收藏
页码：1347 / 1350
页数：4
相关论文
共 50 条
  • [21] NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3)-H Alkylation of Alkenes
    Zhou, Fang
    Zhu, Jin
    Zhang, Yao
    Zhu, Shaolin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (15) : 4058 - 4062
  • [22] Site-Selective Defluorinative sp3 C-H Alkylation of Secondary Amides
    Yue, Wen-Jun
    Day, Craig S.
    Martin, Ruben
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (17) : 6395 - 6400
  • [23] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
    Basle, Olivier
    Li, Chao-Jun
    CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
  • [24] Oxidation and Amination of Benzylic sp3 C-H Bond Catalyzed by Rhenium(V) Complexes
    Peng, Hao
    Lin, Aijun
    Zhang, Yan
    Jiang, Honglai
    Zhou, Jiecong
    Cheng, Yixiang
    Zhu, Chengjian
    Hu, Hongwen
    ACS CATALYSIS, 2012, 2 (01): : 163 - 167
  • [25] C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp3 C-H Activation
    Prokopcova, Hana
    Bergman, Sheba D.
    Aelvoet, Karel
    Smout, Veerle
    Herrebout, Wouter
    Van der Veken, Benjamin
    Meerpoel, Lieven
    Maes, Bert U. W.
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (44) : 13063 - 13067
  • [26] Rhodium-catalyzed alkylation of terephthaldialdimine with terminal alkenes via C-H bond activation
    Lim, YG
    Koo, BT
    TETRAHEDRON LETTERS, 2005, 46 (46) : 7997 - 8001
  • [27] Selective Catalytic C-H Alkylation of Alkenes with Alcohols
    Lee, Dong-Hwan
    Kwon, Ki-Hyeok
    Yi, Chae S.
    SCIENCE, 2011, 333 (6049) : 1613 - 1616
  • [28] Rhodium(I)-catalyzed mono-selective C-H alkylation of benzenesulfonamides with terminal alkenes
    Rej, Supriya
    Chatani, Naoto
    CHEMICAL COMMUNICATIONS, 2019, 55 (71) : 10503 - 10506
  • [29] Iron-Catalyzed Regioselective α-C-H Alkylation of N-Methylanilines: Cross-Dehydrogenative Coupling between Unactivated C(sp3)-H and C(sp3)-H Bonds via a Radical Process
    Li, Ze-Lin
    Sun, Kang-Kang
    Wu, Peng-Yu
    Cai, Chun
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11) : 6830 - 6839
  • [30] Cationic iridium-catalyzed enantioselective activation of secondary sp3 C-H bond adjacent to nitrogen atom
    Pan, Shiguang
    Matsuo, Yusuke
    Endo, Kohei
    Shibata, Takanori
    TETRAHEDRON, 2012, 68 (44) : 9009 - 9015
12345