Versatile application of trifluoromethyl triflate

被引:108
作者
Kolomeitsev, Alexander A. [1 ,2 ]
Vorobyev, Mikhail [2 ]
Gillandt, Hartmut [3 ]
机构
[1] Univ Bremen, Inst Inorgan & Phys Chem, D-28334 Bremen, Germany
[2] Forschungszentrum Julich, Hansa Fine Chem, D-28359 Bremen, Germany
[3] Forschungszentrum Julich, SciChem, D-28359 Bremen, Germany
关键词
trifluoromethyl triflate; trifluoromethanolates; trifluoromethyl ethers; arynes; delocalized lipophilic cations;
D O I
10.1016/j.tetlet.2007.11.105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrolytically stable and easy to handle trifluoromethyl triflate was found to be a liquid reservoir of 'masked' difluorophosgene. Anhydrous F(-) sources cleave the S-O bond in trifluoromethyl triflate yielding quantitatively the trifluoromethanolate salts, being useful trifluoromethoxy group carriers. Reaction of trifluoromethanolates with in situ generated from o-trimethylsilylphenyl triflate benzyne leads to (trifluoromethoxy)benzene and fluorobenzene (ratio 85:15). Whereas an addition of trifluoromethanethiolate anion across a triple bond of benzyne leads to [(trifluoromethyl)sulfanyl]benzene solely. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:449 / 454
页数:6
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