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A new finding in selective Baeyer–Villiger oxidation of α-fluorinated ketones; a new and practical route for the synthesis of α-fluorinated esters by Satoru Kobayashi; Hiroaki Tanaka; Hideki Amii; Kenji Uneyama is a Chemistry article available to read on EtoBox.

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a-Fluorinated esters were effectively prepared by the Baeyer -Villiger oxidation of a-fluorinated ketones with m-chloroperbenzoic acid (m-CPBA) under mild conditions. The yield of the esters was influenced by the choice of solvent, base, and substituent on the aryl group of the ketones. 4-Methoxyphenyl substituted fluoroketones were oxidized almost quantitatively with m-CPBA within 10 min to 12 h at room temperature using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as a cosolvent with CH 2 Cl 2 (1:1, v/v) and aqueous buffer (KH 2 PO 4 -NaOH, pH 7.6) as an additive base. The oxidation reaction rates of a-fluorinated ketones were higher than those of the corresponding non-fluorinated ketones. The fluorine atom at a-position of fluoromethyl aryl ketones enhanced the reactivity in the Baeyer -Villiger oxidation.

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Author

Satoru Kobayashi; Hiroaki Tanaka; Hideki Amii; Kenji Uneyama

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2003

Language

EN

Field

Chemistry (Physical Sciences)