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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 23期
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
  • [31] Copper-mediated oxidative C-H/N-H activations with alkynes by removable hydrazides
    Xiong, Feng
    Li, Bo
    Yang, Chenrui
    Zou, Liang
    Ma, Wenbo
    Gu, Linghui
    Mei, Ruhuai
    Ackermann, Lutz
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 1591 - 1599
  • [32] Copper-mediated C-H amination of 2H-indazoles with N-Fluorobenzenesulfonimide
    Li, Zhenhua
    Ye, Lixian
    Cao, Yingyan
    Qin, Jinjing
    Wang, Wenbiao
    Xie, Yuanyuan
    TETRAHEDRON LETTERS, 2021, 83
  • [33] Copper-Mediated Oxidative Coupling of Benzamides with Maleimides via Directed C-H Cleavage
    Miura, Wataru
    Hirano, Koji
    Miura, Masahiro
    ORGANIC LETTERS, 2015, 17 (16) : 4034 - 4037
  • [34] Progress in Copper-Mediated Functionalization of Unactivated C-H Bonds Assisted by Directing Groups
    Hu Jia-Lei
    Li Jie
    Zhou Yi-Feng
    CURRENT GREEN CHEMISTRY, 2015, 2 (02) : 170 - 191
  • [35] Copper-Mediated Regioselective C-H Sulfenylation and Selenation of Phenols with Phenanthroline Bidentate Auxiliary
    Kajiwara, Rikuo
    Takamatsu, Kazutaka
    Hirano, Koji
    Miura, Masahiro
    ORGANIC LETTERS, 2020, 22 (15) : 5915 - 5919
  • [36] Copper-mediated ortho C-H sulfonylation of benzoic acid derivatives with sodium sulfinates
    Liu, Jidan
    Yu, Lin
    Zhuang, Shaobo
    Gui, Qingwen
    Chen, Xiang
    Wang, Wenduo
    Tan, Ze
    CHEMICAL COMMUNICATIONS, 2015, 51 (29) : 6418 - 6421
  • [37] COPPER-MEDIATED REGIOSELECTIVE HOMOCOUPLING OF THIOPHENES AND INDOLES VIA DIRECTED C-H CLEAVAGE
    Odani, Riko
    Nishino, Mayuko
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    HETEROCYCLES, 2014, 88 (01) : 595 - 602
  • [38] Copper-catalyzed/mediated aromatic C-H bond functionalization
    Zhang, Ming
    APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (04) : 269 - 284
  • [39] Copper-Mediated Selective Mono- and Sequential Organochalcogenation of C-H Bonds: Synthesis of Hybrid Unsymmetrical Aryl Ferrocene Chalcogenides
    Sattar, Moh.
    Patidar, Krishna
    Thorat, Raviraj Ananda
    Kumar, Sangit
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (11): : 6669 - 6678
  • [40] Copper-Mediated C-H Activation/C-S Cross-Coupling of Heterocycles with Thiols
    Ranjit, Sadananda
    Lee, Richmond
    Heryadi, Dodi
    Shen, Chao
    Wu, Ji'En
    Zhang, Pengfei
    Huang, Kuo-Wei
    Liu, Xiaogang
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21): : 8999 - 9007
12345