Catalytic C-H oxidation by a triazamacrocyclic ruthenium complex

被引:66
|
作者
McNeill, Eric [1 ]
Du Bois, J. [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
基金
美国国家科学基金会;
关键词
SATURATED-HYDROCARBONS; RUO4-MEDIATED OXIDATIONS; CIS-DIOXORUTHENIUM(VI) COMPLEX; HYDROXYLATION; MECHANISM; FUNCTIONALIZATION; SELECTIVITY; EPOXIDATION; REACTIVITY; ALKENES;
D O I
10.1039/c2sc20118f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method for oxygenation of tertiary and benzylic C-H bonds is described that uses 1-10 mol% (1,4,7-trimethyl-1,4,7-triazacyclo-nonane) ruthenium(III) trichloride as catalyst and ceric (IV) ammonium nitrate (CAN) as the terminal oxidant. The reaction is conveniently performed in aqueous solvent mixtures on substrates bearing a number of common, polar functional groups. The scope and efficiency of this process are comparable or superior to other known catalytic C-H oxidation technologies. Chemoselectivity trends and kinetic isotope effect data implicate a stepwise, radical-rebound mechanism for this transformation.
引用
收藏
页码:1810 / 1813
页数:4
相关论文
共 50 条
  • [1] Influence of Solvents on Catalytic C-H Bond Oxidation by a Copper(II)-Alkylperoxo Complex
    Lee, Yuri
    Kim, Bohee
    Kim, Seonghan
    Ng, Elvis Wang Hei
    Ariyasu, Shinya
    Shoji, Osami
    Yoon, Sungho
    Hirao, Hajime
    Cho, Jaeheung
    ACS CATALYSIS, 2024, 14 (05) : 3524 - 3532
  • [2] Catalytic Oxidation of Primary C-H Bonds in Alkanes with Bioinspired Catalysts
    Dantignana, Valeria
    Company, Anna
    Costas, Miquel
    CHIMIA, 2020, 74 (06) : 470 - 477
  • [3] Non-Heme-Type Ruthenium Catalyzed Chemo- and Site-Selective C-H Oxidation
    Doiuchi, Daiki
    Nakamura, Tatsuya
    Hayashi, Hiroki
    Uchida, Tatsuya
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (06) : 762 - 765
  • [4] C-H Oxidation by a Diiron Complex with Facially Opposing Active Sites
    Lindsay, Stacey
    Mader, Sophie L.
    Kaila, Ville R. I.
    Hess, Corinna R.
    CHEMISTRYSELECT, 2018, 3 (05): : 1602 - 1608
  • [5] Ruthenium-Catalyzed Hydroxylation of Unactivated Tertiary C-H Bonds
    McNeill, Eric
    Du Bois, J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (29) : 10202 - 10204
  • [6] Nonheme Fe Based Enzyme Mimics for Fine Organic Synthesis: Catalytic C-H and C=C Oxygenations
    Talsi, Evgenii P.
    Bryliakov, Konstantin P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (40)
  • [7] Ruthenium Aqua Complexes Supported by the Klaui Tripodal Ligand: Synthesis, Structure, and Application in Catalytic C-H Oxidation in Water
    So, Yat-Ming
    Wong, Kang-Long
    Sung, Herman H. Y.
    Williams, Ian D.
    Leung, Wa-Hung
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2019, 2019 (18) : 2368 - 2374
  • [8] Catalytic C-H Oxidation Enhances Polyethylene Bonding
    Musolino, Stefania F.
    Wulff, Jeremy E.
    CHEM, 2021, 7 (01): : 7 - 9
  • [9] Enantiotopos-Selective C-H Oxygenation Catalyzed by a Supramolecular Ruthenium Complex
    Frost, James R.
    Huber, Stefan M.
    Breitenlechner, Stefan
    Bannwarth, Christoph
    Bach, Thorsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) : 691 - 695
  • [10] Ruthenium catalysed C-H bond borylation
    Fernandez-Salas, Jose A.
    Manzini, Simone
    Piola, Lorenzo
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    CHEMICAL COMMUNICATIONS, 2014, 50 (51) : 6782 - 6784