Defluorosilylation of Industrially Relevant Fluoroolefins Using Nucleophilic Silicon Reagents

Abstract

Abstract A number of new magnesium and lithium silyl reagents were prepared and shown to be outstanding nucleophiles in reactions with industrially relevant fluoroolefins. These reactions result in a net transformation of either sp 2 or sp 3 C−F bonds into C−Si bonds by two modes of nucleophilic attack (S N V or S N 2′). The methods are mild, proceeding with high chemo‐ and regioselectivity. Mechanistic pathways are described that lead to new substitution patterns from HFO‐1234yf, HFO‐1234ze, and HFO‐1336mzz, previously inaccessible by transition metal catalyzed difluorosilylation routes.