title: Direct α-siladifluoromethylation of lithium enolates with Ruppert-Prakash reagent via C-F bond activation.
abstract: The direct α-siladifluoromethylation of lithium enolates with the Ruppert-Prakash reagent (CF3 TMS) 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F bond activation due to the strong interaction between lithium and fluorine atoms.
authors.affiliation: Department of Applied Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552 (Japan).
authors.forename: Ryota
authors.initials: R
authors.lastname: Hashimoto
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Iida
authors.forename: Kohsuke
authors.initials: K
authors.lastname: Aikawa
authors.forename: Shigekazu
authors.initials: S
authors.lastname: Ito
authors.forename: Koichi
authors.initials: K
authors.lastname: Mikami
mesh_terms: D005461:Fluorine / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*
chemical_list: D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D009861:Onium Compounds; D005461:Fluorine; D008094:Lithium
keywords: CF activation; Ruppert-Prakash reagent; difluoromethylation; lithium enolate; umpolung