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Lewis Acid Catalyzed Synthesis of α-Trifluoromethyl Esters and Lactones by Electrophilic Trifluoromethylation.
Journal article

Lewis Acid Catalyzed Synthesis of α-Trifluoromethyl Esters and Lactones by Electrophilic Trifluoromethylation.

  • Katayev D Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.
  • Matoušek V Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.
  • Koller R Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.
  • Togni A Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.
  • 2015-11-21
Published in:
  • Organic letters. - 2015
Acetals
Catalysis
Esters
Ethylenes
Hydrocarbons, Fluorinated
Iodine
Ketones
Lactones
Lewis Acids
Molecular Structure
English 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%).
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://folia.unifr.ch/global/documents/238824
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