Multigram Laboratory Scale Synthesis of α-Trifluoromethoxy Carbonyl Compounds

被引:23
作者
Barbion, Julien [1 ]
Pazenok, Sergii [2 ]
Vors, Jean-Pierre [3 ]
Langlois, Bernard R. [1 ]
Billard, Thierry [1 ]
机构
[1] Univ Lyon 1, CNRS, ICBMS, UMR 5246, F-69622 Villeurbanne, France
[2] Bayer CropSci AG, Prod Technol, Proc Res, D-40789 Monheim, Germany
[3] Bayer CropSci SAS, Ctr R&D Dargoire, F-69009 Lyon, France
关键词
FLUORINE; TRIFLATE;
D O I
10.1021/op500118r
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
alpha-trifluoromethoxy carbonyl compounds are valuable building blocks for the synthesis of various trifluoromethoxylated compounds. The best way to easily obtain them is the direct trifluoromethoxylation with the CF3O- anion, generated in situ from trifluoromethyl triflate. However, the necessary autogenous pressure generated during this reaction constitutes a main drawback for a multigram scale extrapolation. A specific procedure using adapted glassware has allowed a laboratory large-scale production (up to 50 g) of such building blocks with good yields.
引用
收藏
页码:1037 / 1040
页数:4
相关论文
共 18 条
[1]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
[2]   Polyfluoro- and perfluoroalkoxyenaminones in syntheses of nitrogen containing heterocycles [J].
Davydova, Yulia A. ;
Sokolenko, Taras M. ;
Yagupolskii, Yurii L. .
JOURNAL OF FLUORINE CHEMISTRY, 2014, 157 :58-62
[3]   Fluorinated liquid crystals - properties and applications [J].
Hird, Michael .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (12) :2070-2095
[4]  
Hiyama T., 2013, ORGANOFLUORINE COMPO
[5]   The unique role of fluorine in the design of active ingredients for modern crop protection [J].
Jeschke, P .
CHEMBIOCHEM, 2004, 5 (05) :570-589
[6]   α-fluorinated ethers as "exotic" entity in medicinal chemistry [J].
Jeschke, Peter ;
Baston, Eckhard ;
Leroux, Frederic R. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (10) :1027-1034
[7]  
Kirsch P., 2013, MODERN FLUOROORGANIC
[8]   Versatile application of trifluoromethyl triflate [J].
Kolomeitsev, Alexander A. ;
Vorobyev, Mikhail ;
Gillandt, Hartmut .
TETRAHEDRON LETTERS, 2008, 49 (03) :449-454
[9]  
Langlois B. R, 2013, 245 ACS NAT MEET EXP
[10]   Trifluoromethyl ethers - synthesis and properties of an unusual substituent [J].
Leroux, Frederic R. ;
Manteau, Baptiste ;
Vors, Jean-Pierre ;
Pazenok, Sergiy .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2008, 4