Versatile application of trifluoromethyl triflate

被引：113

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

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 03期

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

页码：449 / 454

页数：6

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