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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 1999-09, Vol.64 (18), p.6717-6723
Hauptverfasser: Uneyama, Kenji, Mizutani, Go, Maeda, Kazushige, Kato, Tsuyoshi
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo990571d