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

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.

SUBMITTER: Raja E

PROVIDER: S-EPMC3286112 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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

Raja Erum E Klumpp Douglas A DA

Tetrahedron letters 20111001 40

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. ...[more]

PMID: 22383858

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