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 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | 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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo990571d |