A Simple and Effective Method for α-Hydroxylation of β-Dicarbonyl Compounds Using Oxone as an Oxidant without a Catalyst

被引：46
|
作者：
Yu, Jun [1 ]
Cui, Jian [1 ]
Zhang, Chi [1 ]
机构：
[1] Nankai Univ, State Key Lab Elementoorgan Chem, Res Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 36期
基金：
中国国家自然科学基金;
关键词：
Synthetic methods; Oxidation; Hydroxylation; Enols; DYE-SENSITIZED PHOTOOXIDATION; 1,3-DICARBONYL COMPOUNDS; OXIDATIVE CLEAVAGE; KETO-ESTERS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC HYDROXYLATION; BIOMIMETIC SYNTHESIS; SELECTIVE CLEAVAGE; FACILE OXIDATION; SECONDARY-AMINES;
D O I：
10.1002/ejoc.201000940
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxone has been found to be a highly efficient reagent for the introduction of a hydroxy group at the a position of a variety of beta-dicarbonyl compounds in the homogeneous solvent mixture of water and 1,4-dioxane at 60 degrees C.
引用
收藏
页码：7020 / 7026
页数：7
相关论文
共 50 条
  • [1] Oxone®-Mediated Direct α-Hydroxylation of β-Dicarbonyl Compounds: Racemic Synthesis of Harzialactone A
    Sa, Marcus M.
    Peterle, Marcos M.
    Marques, Marcelo, V
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2019, 30 (08) : 1779 - 1787
  • [2] A simple method for epoxidation of olefins using sodium chlorite as an oxidant without a catalyst
    Geng, XL
    Wang, Z
    Li, XQ
    Zhang, C
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23): : 9610 - 9613
  • [3] Benzylation of β-dicarbonyl compounds and 4-hydroxycoumarin using TMSOTf catalyst: a simple, mild, and efficient method
    Theerthagiri, Palani
    Lalitha, Appaswami
    TETRAHEDRON LETTERS, 2010, 51 (41) : 5454 - 5458
  • [4] Pyridine-keggin heteropoly compounds as catalyst for hydroxylation of phenol using hydrogen peroxide as oxidant
    Jianmin Wang
    Liang Yan
    Guang Qian
    Gaomeng Lv
    Guixian Li
    Jishuan Suo
    Xiaolai Wang
    Reaction Kinetics and Catalysis Letters, 2007, 91 : 111 - 118
  • [5] Pyridine-keggin heteropoly compounds as catalyst for hydroxylation of phenol using hydrogen peroxide as oxidant
    Wang, Jianmin
    Yan, Liang
    Qian, Guang
    Lv, Gaomeng
    Li, Guixian
    Suo, Jishuan
    Wang, Xiaolai
    REACTION KINETICS AND CATALYSIS LETTERS, 2007, 91 (01): : 111 - 118
  • [6] Catalyst-Free α-Aminoxylation of 1,3-Dicarbonyl Compounds with TEMPO Using Selectfluor as an Oxidant
    Tang, Lin
    Yang, Zhen
    Yang, Fang
    Huang, Yifan
    Chen, Hanfei
    Cheng, Hao
    Song, Weiyan
    Ren, Bo
    Zhou, Qiuju
    CHEMISTRYSELECT, 2019, 4 (41): : 12053 - 12056
  • [7] Controlling Photooxygenation with a Bifunctional Quinine-BODIPY Catalyst: towards Asymmetric Hydroxylation of β-Dicarbonyl Compounds
    Fischer, Jerome
    Mele, Lucas
    Serier-Brault, Helene
    Nun, Pierrick
    Coeffard, Vincent
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (37) : 6352 - 6358
  • [8] Selective and effective oxone-catalysed α-iodination of ketones and 1,3-dicarbonyl compounds in the solid state
    Goswami, Papori
    Ali, Shahzad
    Khan, Md. Musawwer
    Khan, Abu Taleb
    ARKIVOC, 2007, : 82 - 89
  • [9] Oxidation of cornstarch using oxygen as oxidant without catalyst
    Sheng Ye
    Wang Qiu-hua
    Xu Xue-Chun
    Jiang Wen-yong
    Gan Shu-cai
    Zou Hai-Feng
    LWT-FOOD SCIENCE AND TECHNOLOGY, 2011, 44 (01) : 139 - 144
  • [10] A SIMPLE AND EFFICIENT METHOD FOR PREPARING 1,5-DICARBONYL COMPOUNDS
    DUHAMEL, P
    HENNEQUIN, L
    POIRIER, N
    POIRIER, JM
    TETRAHEDRON LETTERS, 1985, 26 (50) : 6201 - 6204
12345