Complex induced proximity effect enhancement in α-silyl carbanion generation. A general conversion of 2-silyl benzamides into 2-fluorosilylacetophenones

LDA treatment of 2-silylated benzamides 1 affords 2-fluorosilylated acetophenones 3 in a general process likely driven by CIPE-facilitated α-silyl carbanion formation and rearrangement (Scheme 3); oxidation (H 2O 2) of the products gives 2-hydroxyacetophenones and catechols (Scheme 4). Graphic

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Bibliographic Details
Published in:Tetrahedron letters 1996-04, Vol.37 (17), p.2915-2918
Main Authors: Brough, Paul A., Fisher, Stephen, Zhao, Baoping, Thomas, Ryan C., Snieckus, Victor
Format: Article
Language:English
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Summary:LDA treatment of 2-silylated benzamides 1 affords 2-fluorosilylated acetophenones 3 in a general process likely driven by CIPE-facilitated α-silyl carbanion formation and rearrangement (Scheme 3); oxidation (H 2O 2) of the products gives 2-hydroxyacetophenones and catechols (Scheme 4). Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)00446-7