Preparation, properties and synthetic potentials of fluorous boronates

A fluorous approach to the chemistry of boronic acids and its application in fluorous-phase techniques are described. Treatment of fluorous bromosilane with allyl Grignard reagent followed by dihydroxylation provided fluorous diol . A series of boronic acids were attached to by esterification. The formed fluorous boronates were moisture sensitive and thus their synthetic potentials were limited. Thus a fluorous pinacol, , was designed and synthesized by treatment of fluorous bromosilane with excess 2,3-dimethyl-2-butyenylmagnesium bromide to afford fluorous tetramethyl ethene , and was dihydroxylated. Compound was successfully used to prepare fluorous boronates in a one-pot process from organic bromides. We have demonstrated that olefin cross-metathesis can be carried out in a fluorous version. It is noteworthy that all of the fluorinated compounds reported in this paper were purified by simple liquid extraction.