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

Org Lett

Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH Zurich , Vladimir-Prelog-Weg 2, CH-8093 Zurich, Switzerland.

Published: December 2015

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%).

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http://dx.doi.org/10.1021/acs.orglett.5b03088DOI Listing

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