Direct α-siladifluoromethylation of lithium enolates with ruppert-prakash reagent via Cï-F bond activation

Abstract

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 Cï-F bond activation due to the strong interaction between lithium and fluorine atoms. Reaching for Ruppert-Prakash: The direct α-siladifluoromethylation of lithium enolates with the Ruppert-Prakash reagent (CF3TMS) is shown to construct tertiary and quaternary carbon centers (see scheme). The Ruppert-Prakash reagent can be employed as a siladifluoromethyl cation (TMSCF2+) equivalent by Cï-F bond activation due to the strong interaction between lithium and fluorine atoms. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.