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
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
  • [1] Hydroxoiridium-Catalyzed Hydroalkylation of Terminal Alkenes with Ureas by C(sp3)-H Bond Activation
    Yamauchi, Daisuke
    Nishimura, Takahiro
    Yorimitsu, Hideki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) : 7200 - 7204
  • [2] Terminal C(sp3)-H alkylation of internal alkenes via Ni/H-catalyzed isomerization
    Wang, Zhen-Yu
    Wan, Jia-Hao
    Wang, Gao-Yin
    Wang, Rui
    Jin, Ruo-Xing
    Lan, Quan
    Wang, Xi-Sheng
    TETRAHEDRON LETTERS, 2018, 59 (23) : 2302 - 2305
  • [3] Iridium-catalyzed sp3 C-H Alkylation of 3-Carbonyl-2-(alkylamino)pyridines with Alkenes
    Nagai, Masaki
    Nagamoto, Midori
    Nishimura, Takahiro
    Yorimitsu, Hideki
    CHEMISTRY LETTERS, 2017, 46 (08) : 1176 - 1178
  • [4] Alkali-amide-catalyzed divergent sp2 and sp3 C-H bonds alkylation of alkylthiophenes with alkenes
    Luo, Yan-Long
    Du, Hui-Zhen
    Guan, Bing-Tao
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (15) : 4171 - 4176
  • [5] Cu-Catalyzed α-Alkylation of Glycine Derivatives for C(sp3)-H/C(sp3)-H Bond Selective Functionalization
    Xiang, Huan
    Ye, Yang
    ACS CATALYSIS, 2023, 14 (01) : 522 - 532
  • [6] Remote sp3 C-H Amination of Alkenes with Nitroarenes
    Xiao, Jichao
    He, Yuli
    Ye, Feng
    Zhu, Shaolin
    CHEM, 2018, 4 (07): : 1645 - 1657
  • [7] Scandium-catalyzed C(sp3)-H alkylation of N, N-dimethyl anilines with alkenes
    Gao, Hongjie
    Su, Jianhong
    Xu, Pengfei
    Xu, Xin
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (01): : 59 - 63
  • [8] 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
  • [9] Ruthenium(II)-Catalyzed C(sp3)-H α-Alkylation of Pyrrolidines
    Schinkel, Marvin
    Wang, Lianhui
    Bielefeld, Kris
    Ackermann, Lutz
    ORGANIC LETTERS, 2014, 16 (07) : 1876 - 1879
  • [10] Copper catalyzed benzylic sp3 C-H alkenylation
    Chen, Ting-An
    Staples, Richard J.
    Warren, Timothy H.
    CHEMICAL SCIENCE, 2024, 15 (42) : 17685 - 17690