Selective C-H bond hydroxylation of cyclohexanes in water by supramolecular control

被引：7
|
作者：
Yang, Bin [1 ,2 ]
Cui, Jian-Fang [1 ,2 ]
Wong, Man Kin [1 ,2 ]
机构：
[1] Hong Kong Polytech Univ, Shenzhen Res Inst, Shenzhen, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, State Key Lab Chirosci, Hong Kong, Hong Kong, Peoples R China
来源：
RSC ADVANCES | 2017年 / 7卷 / 49期
基金：
中国国家自然科学基金;
关键词：
REGIOSELECTIVE INTRAMOLECULAR OXIDATION; GENERATED IN-SITU; BETA-CYCLODEXTRIN; ASYMMETRIC EPOXIDATION; CATALYTIC HYDROXYLATION; HYDROGEN-PEROXIDE; CHIRAL KETONES; DIOXIRANES; FUNCTIONALIZATION; NMR;
D O I：
10.1039/c7ra03930a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new approach for selective hydroxylation of non-activated cyclohexanes using dioxirane generated in situ in water through supramolecular control has been developed. Using beta-CD and gamma-CD as the supramolecular hosts, selective hydroxylation of cyclohexane substrates, including trans/cis-1,4-, 1,3- and 1,2-dimethylcyclohexanes and trans/cis-decahydronaphthalene, was achieved in up to 54% yield in water. Furthermore, site-selective C-H bond hydroxylation of (+)-menthol was achieved by obstructing the approach of dioxirane to the C-H bond with higher steric hindrance through inclusion complexation with beta-CD and gamma-CD in water.
引用
收藏
页码：30886 / 30893
页数：8
相关论文
共 50 条
  • [41] Selective C-H bond functionalization using repurposed or artificial metalloenzymes
    Upp, David M.
    Lewis, Jared C.
    CURRENT OPINION IN CHEMICAL BIOLOGY, 2017, 37 : 48 - 55
  • [42] A General Catalyst for the β-Selective C-H Bond Arylation of Thiophenes with Iodoarenes
    Ueda, Kirika
    Yanagisawa, Shuichi
    Yamaguchi, Junichiro
    Itami, Kenichiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (47) : 8946 - 8949
  • [43] Selective C-H bond activation of arenes catalyzed by methylrhenium trioxide
    Jacob, J
    Espenson, JH
    INORGANICA CHIMICA ACTA, 1998, 270 (1-2) : 55 - 59
  • [44] Site-Selective C-H Bond Functionalization of Chromones and Coumarins
    Kang, Dahye
    Ahn, Kukcheol
    Hong, Sungwoo
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) : 1136 - 1150
  • [45] Selective C-H bond activation of ethane by free gold clusters
    Lang, Sandra M.
    Bernhardt, Thorsten M.
    Bakker, Joost M.
    Yoon, Bokwon
    Landman, Uzi
    INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2019, 435 : 241 - 250
  • [46] Selective oxidative β-C-H bond sulfenylation of tetrahydroisoquinolines with elemental sulfur
    Guo, Tao
    Bi, Lei
    Shen, Lu
    Wei, Quanhong
    Zhu, Congjun
    Zhang, Panke
    Zhao, Yunhui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 21 (01) : 127 - 131
  • [47] Selective C-H Bond Cleavage in Methane by Small Gold Clusters
    Lang, Sandra M.
    Bernhardt, Thorsten M.
    Chernyy, Valeriy
    Bakker, Joost M.
    Barnett, Robert N.
    Landman, Uzi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) : 13406 - 13410
  • [48] Role of confinement in selective C-H bond activations in MoV oxides
    Liu, Yilang
    Leelavathi, Annamalai
    Ezenwa, Sopuruchukwu
    Deshlahra, Prashant
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [49] Selective C-H bond activation of arenes catalyzed by methylrhenium trioxide
    Ames Laboratory, Department of Chemistry, Iowa State University, Ames, IA 50011, United States
    Inorg. Chim. Acta, 1-2 (55-59):
  • [50] Electrochemical C-H Hydroxylation and Alkoxylation Reactions
    Wang, Huiqiao
    Zhang, Guangwu
    Xu, Kun
    CHEMSUSCHEM, 2024,
12345