Direct α-Siladifluoromethylation of Lithium Enolates with Ruppert-Prakash Reagent via C[BOND]F Bond Activation



The direct α-siladifluoromethylation of lithium enolates with the Ruppert–Prakash reagent (CF3TMS) is shown to construct the tertiary and quaternary carbon centers. The Ruppert–Prakash reagent, which is versatile for various trifluoromethylation as a trifluoromethyl anion (CF3) equivalent, can be employed as a siladifluoromethyl cation (TMSCF2+) equivalent by C[BOND]F bond activation due to the strong interaction between lithium and fluorine atoms.