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. 2011 Oct 5;52(40):5170-5172.
doi: 10.1016/j.tetlet.2011.07.125.

Fluoro-substituted ketones from nitriles using acidic and basic reaction conditions

Erum Raja  1 , Douglas A Klumpp
Affiliations

Fluoro-substituted ketones from nitriles using acidic and basic reaction conditions

Erum Raja et al. Tetrahedron Lett. .

Abstract

Fluoro-substituted aliphatic nitriles are shown to undergo the Houben-Hoesch reactions with arenes in CF(3)SO(3)H to give fluoro-substituted ketones in good yields. The fluorine substituents appear to enhance the reactivities of the nitriles (and the nitrilium ion intermediates) compared to similar aliphatic nitriles. Fluoro-substituted ketones are also shown to be accessible through the reactions of organometallic reagents and fluoro-substituted nitriles.

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Figures

Figure 1
Figure 1
Superacid-promoted reactions of fluoro-substituted acetonitriles.
See this image and copyright information in PMC

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