Ligand-Free, Copper-Catalyzed Aerobic Benzylic sp3 C-H Oxygenation

被引:23
|
作者
Tanaka, Hirotaka [1 ]
Oisaki, Kounosuke [1 ]
Kanai, Motomu [1 ,2 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
[2] Japan Sci & Technol Agcy JST, Kanai Life Sci Catalysis Project, ERATO, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan
关键词
sp(3) C-H oxygenation; copper; oxygen; ligand-free; benzylic oxidation; MOLECULAR-OXYGEN; TERMINAL OXIDANT; EFFICIENT SYNTHESIS; MILD CONDITIONS; AMINO-ACIDS; OXIDATION; BONDS; FUNCTIONALIZATION; SYSTEM; ETHERS;
D O I
10.1055/s-0036-1588969
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A ligand-free and operationally simple copper-catalyzed aerobic benzylic sp(3) C-H oxygenation was developed. The addition of tertbutyl hydroperoxide, either in a catalytic or stoichiometric amount, was key for activating stable C-H bonds under mild conditions to furnish the corresponding ketones or esters in moderate to excellent yield.
引用
收藏
页码:1576 / 1580
页数:5
相关论文
共 50 条
  • [1] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
    Basle, Olivier
    Li, Chao-Jun
    CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
  • [2] Copper catalyzed benzylic sp3 C-H alkenylation
    Chen, Ting-An
    Staples, Richard J.
    Warren, Timothy H.
    CHEMICAL SCIENCE, 2024, 15 (42) : 17685 - 17690
  • [3] Copper-Catalyzed sp3 C-H Amination
    Gephart, Raymond T., III
    Warren, Timothy H.
    ORGANOMETALLICS, 2012, 31 (22) : 7728 - 7752
  • [4] Copper-catalyzed benzylic oxidation of C(sp3)-H bonds
    Zhang, Bo
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    TETRAHEDRON, 2013, 69 (08) : 2033 - 2037
  • [5] Copper-catalyzed benzylic C(sp3)-H alkoxylation of heterocyclic compounds
    Takemura, Noriaki
    Kuninobu, Yoichiro
    Kanai, Motomu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (16) : 2528 - 2532
  • [6] Copper-Catalyzed Benzylic sp3 C-H Amination Reaction of Amidines : Synthesis of Quinazoline Derivatives
    Zhang Qian
    Lu Yunhe
    Li Yan
    Xiong Tao
    Zhang Qian
    ACTA CHIMICA SINICA, 2014, 72 (11) : 1139 - 1143
  • [7] Copper-catalyzed oxidative trifluoromethylation of benzylic sp3 C-H bond adjacent to nitrogen in amines
    Mitsudera, Hiromasa
    Li, Chao-Jun
    TETRAHEDRON LETTERS, 2011, 52 (16) : 1898 - 1900
  • [8] Copper-Catalyzed Aerobic Benzylic C(sp3)-H Oxidation of Unprotected Aniline Derivatives for the Synthesis of Phenanthridines
    Nozawa-Kumada, Kanako
    Matsuzawa, Yuta
    Hayashi, Masahito
    Kobayashi, Takumi
    Shigeno, Masanori
    Yada, Akira
    Kondo, Yoshinori
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) : 2241 - 2245
  • [9] Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones
    Nozawa-Kumada, Kanako
    Matsuzawa, Yuta
    Ono, Kanako
    Shigeno, Masanori
    Kondo, Yoshinori
    CHEMICAL COMMUNICATIONS, 2021, 57 (69) : 8604 - 8607
  • [10] Copper-catalyzed aerobic aliphatic C-H oxygenation with hydroperoxides
    Too, Pei Chui
    Tnay, Ya Lin
    Chiba, Shunsuke
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1217 - 1225