Pd-catalyzed arylation of silyl enol ethers of substituted α-fluoroketones

被引：46

作者：

Guo, Yong ^{[1
]}

Twamley, Brendan ^{[1
]}

Shreeve, Jean'ne M. ^{[1
]}

机构：

[1] Univ Idaho, Dept Chem, Moscow, ID 83844 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 08期

关键词：

CHIRAL PALLADIUM COMPLEXES; BETA-KETO-ESTERS; ENANTIOSELECTIVE FLUORINATION; ASYMMETRIC FLUORINATION; ARYL BROMIDES; ALLYLATION REACTION; KETOESTERS; FLUORIDE; CARBON;

D O I：

10.1039/b900311h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Fluoro-alpha-aryl-ketones were synthesized by the Pd-catalyzed cross-coupling of aryl bromides with either alpha-fluoroketones or their corresponding silyl enol ethers. The direct arylation with an alpha-fluoroketone requires a strong base, such as potassium tert-butoxide, and under these conditions the presence of a base-sensitive functional group is not compatible. However, good functional tolerance was achieved when the anionic coupling moieties were generated from the silyl enol ethers obtained by reacting alpha-fluoroketones with tetrabutylammonium (triphenylsilyl) difluorosilicate (TBAT) as the fluoride source under nearly neutral conditions. The aryl halides with a carbmethoxy, nitro, cyano or carbonyl group were used. The reaction with nonfluorinated silyl enol ether 1h gave a cross-coupling product in low yield.

引用

页码：1716 / 1722

页数：7

共 36 条

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