Chemoselective Trifluoromethylation of Methyl Esters Using an Et3GeNa/C6H5SCF3 Combination: Efficient Synthesis of Trifluoromethyl Ketones

Yasuo Yokoyama; Kunio Mochida

doi:10.1055/s-1997-961

Synlett 1997; 1997(8): 907-908
DOI: 10.1055/s-1997-961

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Chemoselective Trifluoromethylation of Methyl Esters Using an Et₃GeNa/C₆H₅SCF₃ Combination: Efficient Synthesis of Trifluoromethyl Ketones

Yasuo Yokoyama^* , Kunio Mochida¹

^*Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171, Japan

Abstract

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Various trifluoromethyl ketones were synthesized from the corresponding methyl esters by effective nucleophilic trifluoromethylation using an Et₃GeNa/C₆H₅SCF₃ combination. This trifluoromethylation proceeded chemoselectively. When, cyclohexyl, i-propyl and t-butyl esters coexisted in the reaction system, only the methyl ester was easily transformed to the desired compounds in excellent yield. Furthermore, some protective groups were remained under this reaction condition.

Et₃GeNa - C₆H₅SCF₃ - trifluoromethylation - methyl ester - chemoselective

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