Copper-mediated selective oxidation of a C-H bond

被引:40
|
作者
Boldron, C
Gamez, P
Tooke, DM
Spek, AL
Reedijk, J
机构
[1] Leiden Univ, Leiden Inst Chem, Gorlaeus Labs, NL-2300 RA Leiden, Netherlands
[2] Univ Utrecht, Dept Crystal & Struct Chem, NL-3584 CH Utrecht, Netherlands
关键词
biomimetic synthesis; C-H activation; copper; homogeneous catalysis; oxidation;
D O I
10.1002/anie.200462946
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) An environmentally friendly procedure has been developed for the oxidation of 2,4,6-trimethylpheriol (TMP) at the para Csp3-H bond. Upon reaction with H2O2 in the presence of catalytic amounts of CuII and neocuproine in methanol at 65°C, 4-(methoxymethyl)-2,6-dimethylphenol (MDP) or 4-hydroxy-3,5- dimethylbenzaldehyde (HDB) is formed (see reaction). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3585 / 3587
页数:3
相关论文
共 50 条
  • [21] Regiocontrolled palladium-catalyzed and copper-mediated C-H bond functionalization of protected l-histidine
    Mahindra, Amit
    Jain, Rahul
    Organic and Biomolecular Chemistry, 2014, 12 (23): : 3792 - 3796
  • [22] Copper-Mediated Cyanation of Aryl C-H Bond with Removable Bidenate Auxiliary Using Acetonitrile as the Cyano Source
    Yu, Zhengwei
    Zhang, Saisai
    Shen, Zengming
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (12) : 1139 - 1142
  • [23] Regiocontrolled palladium-catalyzed and copper-mediated C-H bond functionalization of protected L-histidine
    Mahindra, Amit
    Jain, Rahul
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (23) : 3792 - 3796
  • [24] Copper-Mediated and Catalyzed C-H Bond Amination via Chelation Assistance: Scope, Mechanism and Synthetic Applications
    Ma, Jiao-Li
    Zhou, Xu-Ming
    Guo, Peng-Hu
    Cheng, Hui-Cheng
    Ji, Hong-bing
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (10) : 1204 - 1223
  • [25] Copper-Mediated Selective C-H Activation and Cross-Dehydrogenative C-N Coupling of 2′-Aminoacetophenones
    Ilangovan, Andivelu
    Satish, Gandhesiri
    ORGANIC LETTERS, 2013, 15 (22) : 5726 - 5729
  • [26] Copper-Mediated Remote Highly Site-Selective C-H Bond Bromination and Chlorination of Quinolines at the C5 Position that is Geometrically Difficult to Access
    Rao, Naidu Sambasiva
    Reddy, Ganapam Manohar
    Sridhar, B.
    Sarma, Maheswaran Harihara
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (03) : 438 - 442
  • [27] Copper-Mediated Enantioselective C-H Thiolation of Ferrocenes Enabled by the BINOL Ligand
    Ma, Jia-Yi
    Yao, Qi-Jun
    Jiang, Lu-Chen
    Huang, Fan-Rui
    Yue, Qiang
    Shi, Bing-Feng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (08) : 7061 - 7069
  • [28] C-H bond halogenation catalyzed or mediated by copper: an overview
    Hao, Wenyan
    Liu, Yunyun
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 2132 - 2144
  • [29] Copper-mediated stereospecific C-H oxidative sulfenylation of terminal alkenes with disulfides
    Tu, Hai-Yong
    Hu, Bo-Lun
    Deng, Chen-Liang
    Zhang, Xing-Guo
    CHEMICAL COMMUNICATIONS, 2015, 51 (85) : 15558 - 15561
  • [30] Copper-Mediated C-H/C-H Biaryl Coupling of Benzoic Acid Derivatives and 1,3-Azoles
    Nishino, Mayuko
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (16) : 4457 - 4461