COMPLEX-INDUCED PROXIMITY EFFECT ENHANCEMENT IN ALPHA-SILYL CARBANIONGENERATION - A GENERAL CONVERSION OF 2-SILYL BENZAMIDES INTO 2-FLUOROSILYLACETOPHENONES

Authors
BROUGH PA FISHER S ZHAO BP THOMAS RC SNIECKUS V
Citation
Pa. Brough et al., COMPLEX-INDUCED PROXIMITY EFFECT ENHANCEMENT IN ALPHA-SILYL CARBANIONGENERATION - A GENERAL CONVERSION OF 2-SILYL BENZAMIDES INTO 2-FLUOROSILYLACETOPHENONES, Tetrahedron letters, 37(17), 1996, pp. 2915-2918
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
17
Year of publication
1996
Pages
2915 - 2918
Database
ISI
SICI code
0040-4039(1996)37:17<2915:CPEEIA>2.0.ZU;2-I
Abstract
LDA treatment of 2-silylated benzamides 1 affords 2-fluorosilylated ac etophenones 3 in a general process likely driven by CIPE-facilitated a lpha-silyl carbanion formation and rearrangement (Scheme 3); oxidation (H2O2) of the products gives 2-hydroxyacetophenones and catechols (Sc heme 4). (C) 1996 Elsevier Science Ltd