Micellar-System-Mediated Direct Fluorination of Ketones in Water

被引:44
|
作者
Stavber, Gaj [2 ]
Zupan, Marko [2 ]
Stavber, Stojan [1 ]
机构
[1] Jozef Stefan Inst, Organ & Bioorgan Chem Lab, Ljubljana 1000, Slovenia
[2] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia
关键词
ketones; halogenation; micelles; F-TEDA-BF4; water; SODIUM DODECYL-SULFATE; HYDROGEN-PEROXIDE; ELECTROPHILIC FLUORINATION; MEDICINAL CHEMISTRY; ALPHA-FLUORINATION; ORGANIC-REACTIONS; SELECTFLUOR; BROMINATION; F-TEDA-BF4; SOLVENT;
D O I
10.1055/s-0028-1087924
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A micellar system was developed and applied for direct regioselective fluorination of a variety of cyclic and acyclic ketones to alpha-fluoroketones in water as reaction medium with Selectflour F-TEDA-BF4 as fluorinating reagent. The inexpensive ionic amphiphile sodium dodecyl sulfate (SDS) was found to be all excellent promoter for fluorofunctionalization of hydrophobic ketones without prior activation or Use of acid catalysts.
引用
收藏
页码:589 / 594
页数:6
相关论文
共 50 条
  • [1] Direct organocatalytic α-fluorination of aldehydes and ketones
    Enders, D
    Hüttl, MRM
    SYNLETT, 2005, (06) : 991 - 993
  • [2] AEROSOL DIRECT FLUORINATION - SYNTHESES OF PERFLUORO KETONES
    ADCOCK, JL
    ROBIN, ML
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14): : 2437 - 2439
  • [3] AEROSOL DIRECT FLUORINATION - INDIRECT SYNTHESES OF PERFLUOROCYCLIC KETONES
    ADCOCK, JL
    ROBIN, ML
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (01): : 191 - 193
  • [4] Direct α-fluorination of ketones using N-F reagents
    Stavber, S
    Jereb, M
    Zupan, M
    SYNTHESIS-STUTTGART, 2002, (17): : 2609 - 2615
  • [5] Synthesis of perfluorinated ketones by utilizing liquid-phase direct fluorination
    Okazoe, Takashi
    Watanabe, Kunio
    Itoh, Masahiro
    Shirakawa, Daisuke
    Takagi, Hirokazu
    Kawahara, Kengo
    Tatematsul, Shin
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2007, 80 (08) : 1611 - 1616
  • [6] SURFACTANT MEDIATED EXTRACTION OF TRITERPENES AND THEIR DIRECT HPLC ANALYSIS FROM THE MICELLAR SYSTEM
    Schneider, P.
    Hosseiny, S. S.
    Bischoff, F.
    Mueller, U.
    Bart, H. J.
    Schlitter, K.
    Jordan, V.
    INSTRUMENTATION SCIENCE & TECHNOLOGY, 2011, 39 (05) : 407 - 418
  • [7] Direct α-Alkylation of Ketones with Alcohols in Water
    Xu, Guoqiang
    Li, Qiong
    Feng, Jiange
    Liu, Qiang
    Zhang, Zuojun
    Wang, Xicheng
    Zhang, Xiaoyun
    Mu, Xindong
    CHEMSUSCHEM, 2014, 7 (01) : 105 - 109
  • [8] ALPHA-FLUORINATION OF KETONES .1. DIRECT FLUORINATION OF PYRUVIC-ACID DERIVATIVES BY USING MOLECULAR FLUORINE
    TSUSHIMA, T
    KAWADA, K
    TSUJI, T
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (06): : 1107 - 1110
  • [9] Effect of acid catalysis on the direct electrophilic fluorination of ketones, ketals, and enamides using Selectfluor™
    Liu, Jack
    Chan, Johann
    Bryant, Craig M.
    Duspara, Petar A.
    Lee, Ernest E.
    Powell, David
    Yang, Hua
    Liu, Ziping
    Walpole, Chris
    Roberts, Edward
    Batey, Robert A.
    TETRAHEDRON LETTERS, 2012, 53 (24) : 2971 - 2975
  • [10] Multiphase minireactor system for direct fluorination of ethylene carbonate
    Lang, P.
    Hill, M.
    Krossing, I.
    Woias, P.
    CHEMICAL ENGINEERING JOURNAL, 2012, 179 : 330 - 337