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 or sp C-F bonds into C-Si bonds by two modes of nucleophilic attack (S V or S 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.
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