Electroreductive defluorination of trifluoromethyl ketones and trifluoroacetic acid derivatives

被引：76

作者：

Uneyama, K ^{[1
]}

Mizutani, G ^{[1
]}

Maeda, K ^{[1
]}

Kato, T ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 18期

关键词：

D O I：

10.1021/jo990571d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha-alkylation of 10 with electrophiles such as aldehydes, ketones, imine, acylhalides, and alkylhalides provided alpha-alkylated-alpha,alpha-difluoroacetates in good to excellent yields.

引用

页码：6717 / 6723

页数：7

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