Hydroxoiridium-Catalyzed Hydroalkylation of Terminal Alkenes with Ureas by C(sp3)-H Bond Activation

被引:39
|
作者
Yamauchi, Daisuke [1 ]
Nishimura, Takahiro [1 ]
Yorimitsu, Hideki [1 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
关键词
alkenes; C-H activation; iridium; reaction mechanisms; synthetic methods; C-H BOND; LIGHT PHOTOREDOX CATALYSIS; ALPHA-AMINOALKYL RADICALS; CYCLIC AMINES; NITROGEN ATOM; FUNCTIONALIZATION REACTIONS; ORGANIC-SYNTHESIS; COUPLING REACTION; DIRECTING GROUPS; VINYL ETHERS;
D O I
10.1002/anie.201702169
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Direct alkylation of a methyl group, on di- and trisubstituted ureas, with terminal alkenes by C(sp(3))-H bond activation proceeded in the presence of a hydroxoiridium/bisphosphine catalyst to give high yields of the corresponding addition products. The hydroxoiridium/bisphosphine complex generates an amidoiridium intermediate by reaction with ureas having an N-H bond.
引用
收藏
页码:7200 / 7204
页数:5
相关论文
共 50 条
  • [41] Enantioselective Nickel-Catalyzed C(sp3)-H Activation of Formamides
    Wang, Yin-Xia
    Zhang, Feng-Ping
    Chen, Hao
    Li, Yue
    Li, Jiang-Fei
    Ye, Mengchun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (42)
  • [42] Ethynyl-Directed Dual C(sp3)-H Activation Polymerization to Construct Regio- and Stereoregular C(sp3)-C(sp3) Bond Polymers
    Wang, Jia
    Li, Mingzhao
    Xu, Liguo
    Huang, Die
    Qin, Anjun
    Wang, Xin
    MACROMOLECULES, 2023, 57 (01) : 122 - 131
  • [43] Rhodium-catalyzed alkylation of terephthaldialdimine with terminal alkenes via C-H bond activation
    Lim, YG
    Koo, BT
    TETRAHEDRON LETTERS, 2005, 46 (46) : 7997 - 8001
  • [44] Palladium-Catalyzed C(sp3)-H Bond Functionalization of Aliphatic Amines
    He, Chuan
    Whitehurst, William G.
    Gaunt, Matthew J.
    CHEM, 2019, 5 (05): : 1031 - 1058
  • [45] Modular synthesis of dihydro-isoquinolines: palladium-catalyzed sequential C(sp2)-H and C(sp3)-H bond activation
    Liu, Weidong
    Yu, Qingzhen
    Hu, Le'an
    Chen, Zenghua
    Huang, Jianhui
    CHEMICAL SCIENCE, 2015, 6 (10) : 5768 - 5772
  • [46] Palladium-Catalyzed Diacetoxylation of Methylenecyclopropanes via C(SP3)-C(SP3) Bond Breaking
    Jiang, Min
    Shi, Min
    ORGANOMETALLICS, 2009, 28 (19) : 5600 - 5602
  • [47] sp3 C-H Bond Activation with Ruthenium(II) Catalysts and C(3)-Alkylation of Cyclic Amines
    Sundararaju, Basker
    Achard, Mathieu
    Sharma, Gangavaram V. M.
    Bruneau, Christian
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) : 10340 - 10343
  • [48] Remote C(sp3)-H activation: palladium-catalyzed intermolecular arylation and alkynylation with organolithiums and terminal alkynes
    Chen, Peng
    Wang, Zhi-Yong
    Wang, Jia-Xin
    Peng, Xiao-Shui
    Wong, Henry N. C.
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (13): : 3438 - 3445
  • [49] Rhodium(I)-Catalyzed Cycloisomerization of Homopropargylallene-Alkynes through C(sp3)-C(sp) Bond Activation
    Kawaguchi, Yasuaki
    Yabushita, Kenya
    Mukai, Chisato
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (17) : 4707 - 4711
  • [50] Recent Advances in the Synthesis of Heterocyclic Compounds via Pd-Catalyzed C(sp3)-H Bond Activation
    Zhao, Kang
    Yang, Lei
    Liu, Jianhua
    Xia, Chungu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (11) : 2833 - 2857