Onium Fluoride for Selective Molecular Transformation

Abstract

In the course of our research into novel and powerful transformation catalyzed by organic bases, we recently focused on the onium amides generated from well soluble organofluoride and dialkylaminosilanes for deprotonative reactions. These studies have not been well investigated in spite of their potential capability to react as a strong base. Here we report the development of the 1,2-addition of phenylacetylene promoted by tetrabutylammonium fluoride catalyst and trimethylsilyl dimethylamine. For deprotonation of heteroaromatics, the combination of phosphazenium fluoride (P5F) catalyst developed by Schwesinger and TMSNMe₂ was found to be effective, furnishing the corresponding adducts in good yields. Further optimization of the reaction conditions and investigation on the scope and limitation are underway.