Electroreductive Defluorination of Trifluoromethyl Ketones and Trifluoroacetic Acid Derivatives

Electroreductive Defluorination of Trifluoromethyl Ketones and Trifluoroacetic Acid Derivatives

Difluoroenol silyl ethers 5 and 6, difluoroketene silyl (O,O-, O,S-, and O,N-) acetals 9 and 21, and 2,2-difluoro-2-trimethylsilylacetates 10 were prepared by electroreductive defluorination of trifluoromethyl ketones and trifluoroacetic acid derivatives in an MeCN−TBAB−chlorotrialkylsilane system u...

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Veröffentlicht in:Journal of organic chemistry 1999-09, Vol.64 (18), p.6717-6723
Hauptverfasser: Uneyama, Kenji, Mizutani, Go, Maeda, Kazushige, Kato, Tsuyoshi
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container_end_page 6723
container_issue 18
container_start_page 6717
container_title Journal of organic chemistry
container_volume 64
creator Uneyama, Kenji
Mizutani, Go
Maeda, Kazushige
Kato, Tsuyoshi
description Difluoroenol silyl ethers 5 and 6, difluoroketene silyl (O,O-, O,S-, and O,N-) acetals 9 and 21, and 2,2-difluoro-2-trimethylsilylacetates 10 were prepared by electroreductive defluorination of trifluoromethyl ketones and trifluoroacetic acid derivatives in an MeCN−TBAB−chlorotrialkylsilane system using a carbon rod as an anode and a lead plate as a cathode. TBAF- or KF−CuI-promoted α-alkylation of 10 with electrophiles such as aldehydes, ketones, imine, acylhalides, and alkylhalides provided α-alkylated-α,α-difluoroacetates in good to excellent yields.
doi_str_mv 10.1021/jo990571d
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title Electroreductive Defluorination of Trifluoromethyl Ketones and Trifluoroacetic Acid Derivatives
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