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

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Organic & Biomolecular Chemistry Vol - 7 Issue - 7

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

Content Provider	Royal Society of Chemistry (RSC)
Author	Twamley, Brendan Shreeve, Jean'ne M. Guo, Yong
Copyright Year	2009
Abstract	α-Fluoro-α-aryl-ketones were synthesized by the Pd-catalyzed cross-coupling of aryl bromides with either α-fluoroketones or their corresponding silyl enol ethers. The direct arylation with an α-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 α-fluoroketones with tetrabutylammonium (tripheny1silyl)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.
Starting Page	1716
Ending Page	1722
Page Count	7
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	7
Issue Number	8
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b900311h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Fluoride Tetra-n-butylammonium bromide Silyl enol ether Potassium tert-butoxide Enol Aryl Carbonyl group Functional group
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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