Cocatalysis in phase-transfer catalyzed fluorination of alkyl halides and sulfonates

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• 作者：M脛脛kosza ; M. ; Bujok ; R.
• 关键词：Fluorination ; Phase-transfer catalysis ; Tin compounds ; Cocatalysis hypervalent anions of tin ; Silicon ; Germanium
• 刊名：Journal of Fluorine Chemistry
• 出版年：2005
• 期刊代码：52_00221139
• 类别：ch
• 出版时间：February, 2005
• 卷：126
• 期：2
• 页码：209-216
• 文件大小：377 K

摘要

Phase-transfer catalyzed (PTC) fluorination of alkyl halides and sulfonates with solid KF proceeds efficiently when cocatalyst triphenyltin fluoride is used. The cocatalytic action of the tin compound consists in continuous formation of difluorotriphenylstannate anion that as the tetraalkyloammonium salt enter the solution where it reacts with alkyl halides to produce alkyl fluorides. The cocatalytic system was used to synthesis of 1,1-difluoroalkanes in two steps from aldehydes. A new kind of PTC was elaborated in which Ph₃SnF acts as phase transfer catalyst via continuous formation of potassium salts of diflurotriphenylstannate anions soluble in dipolar aprotic solvents. A new, simple and general method of synthesis of tetraalkylammonium and potassium salts of difluorotriorgano-tin, silicon and germanium anions is reported.