Anhydrous Tetrabutylammonium Fluoride

作者：Haoran Sun, Stephen G. DiMagno · 发表于：Journal of the American Chemical Society · 年份：2005 · DOI：10.1021/ja0440497 · 被引用次数：383 · 研究领域：Fluorine in Organic Chemistry、Chemical Synthesis and Analysis、Synthesis and Reactions of Organic Compounds

Tetrabutylammonium fluoride (TBAF) is prepared at low temperature by nucleophilic aromatic substitution of hexafluorobenzene with tetrabutylammonium cyanide. Adventitious water is scavenged during this synthesis by the generated hexacyanobenzene, which readily adds water under basic conditions. Contrary to expectations, TBAF is stable to Hofmann elimination in polar aprotic solvents under anhydrous conditions. Added hydroxylic solvents are shown to catalyze the decomposition of TBAF and to catalyze proton exchange with DMSO. The synthetic utility of this salt is described briefly.