title: Lewis Acid Catalyzed Synthesis of α-Trifluoromethyl Esters and Lactones by Electrophilic Trifluoromethylation.
abstract: An electrophilic trifluoromethylation of ketene silyl acetals (KSAs) by hypervalent iodine reagents 1 and 2 has been developed. The reaction proceeds under very mild conditions in the presence of a catalytic amount of trimethylsilyl bis(trifluoromethanesulfonyl)imide (up to 2.5 mol %) as a Lewis acid providing a direct access to a variety of secondary, tertiary, and quaternary α-trifluoromethyl esters and lactones in high yield (up to 98%).
authors.affiliation: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.
authors.forename: Dmitry
authors.initials: D
authors.lastname: Katayev
authors.affiliation: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.
authors.forename: Václav
authors.initials: V
authors.lastname: Matoušek
authors.affiliation: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.
authors.forename: Raffael
authors.initials: R
authors.lastname: Koller
authors.affiliation: Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.
authors.forename: Antonio
authors.initials: A
authors.lastname: Togni
mesh_terms: D000080:Acetals / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D005030:Ethylenes / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000080:Acetals; D004952:Esters; D005030:Ethylenes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D007783:Lactones; D058116:Lewis Acids; D007455:Iodine; C008223:ketene