The Journal of Organic Chemistry

Fluoride ion-catalyzed reduction of aldehydes and ketones with hydrosilanes. Synthetic and mechanistic aspects and an application to the threo-directed reduction of. …

M Fujita, T Hiyama

Index: Fujita, Makoto; Hiyama, Tamejiro Journal of Organic Chemistry, 1988 , vol. 53, # 23 p. 5405 - 5415

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Citation Number: 140

Abstract

Reduction of aldehydes and ketones with hydrosilanes proceeded in the presence of a catalytic amount of tetrabutylammonium fluoride or tris (diethy1amino) sulfonium difluorotrimethylsilicate in aprotic polar solvents under mild conditions. A significant isotope effect (kH/kD= 1.50) was observed in competitive reduction of acetophenone with HSiMezPh and DSiMe2Ph. The reaction was of first order in the concentration of an aprotic polar ...

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