Fluoride-catalyzed conversion of acylsilanes to aldehydes and ketones

Abstract

Acylsilanes undergo efficient protodesilylation upon treatment with fluoride ion in moist DMSO, HMPT, or THF. The reaction is also catalyzed by methoxide ion in methanol or DMSO, but not by chloride ion or bromide ion. Fluoride-catalyzed desilylation in the presence of alkyl halides, aldehydes, or ketones results in modest yields of the corresponding alkylated products.