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] Multifunctionalization of alkenes via aerobic oxynitration and sp3 C-H oxidation
    Taniguchi, Tsuyoshi
    Sugiura, Yuki
    Hatta, Takashi
    Yajima, Atsushi
    Ishibashi, Hiroyuki
    CHEMICAL COMMUNICATIONS, 2013, 49 (22) : 2198 - 2200
  • [22] A Catalytic Alkylation of Ketones via sp3 C-H Bond Activation
    Peng, Xue
    Hirao, Yuki
    Yabu, Shunsuke
    Sato, Hirofumi
    Higashi, Masahiro
    Akai, Takuya
    Masaoka, Shigeyuki
    Mitsunuma, Harunobu
    Kanai, Motomu
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (10): : 6333 - 6346
  • [23] Surgical Cleavage of Unstrained C(sp3)-C(sp3) Bonds in General Alcohols for Heteroaryl C-H Alkylation and Acylation
    Wang, Yaxin
    Yang, Le
    Liu, Shuai
    Huang, Lixia
    Liu, Zhong-Quan
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (19) : 4568 - 4574
  • [24] Noninnocent Azo-Aromatic Cobalt(II)-Catalyzed sp3 C-H Alkylation of Fluorenes with Alcohols
    Kamal
    Samanta, Subhas
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 1910 - 1926
  • [25] Iridium(I)-Catalyzed α-C(sp3)-H Alkylation of Saturated Azacycles
    Verma, Pritha
    Richter, Jeremy M.
    Chekshin, Nikita
    Qiao, Jennifer X.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (11) : 5117 - 5125
  • [26] Pd-catalyzed arylation of Sp3 C-H bonds
    Daugulis, Olafs
    Khan, Rana Kashif M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 132 - 132
  • [27] Pd(II)-Catalyzed Olefination of sp3 C-H Bonds
    Wasa, Masayuki
    Engle, Keary M.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) : 3680 - +
  • [28] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways
    Chen, Xiao
    Goodhue, Charles E.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12634 - 12635
  • [29] Metal-catalyzed functionalization of sp3 C-H bond
    Yun, Sang Young
    Wang, Kung-Pern
    Mamidipalli, Phani
    Lee, Nam-Kyu
    Lee, Daesung
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [30] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: Two distinct C-H activation pathways
    Chen, Xiao
    Goodhue, Charles E.
    Yu, Jin-Quan
    Journal of the American Chemical Society, 2006, 128 (39): : 12634 - 12635
12345