213339-79-8Relevant academic research and scientific papers
Highly reactive trialkylsilylation reagents derived from bis(trifluoromethanesulfonyl)imide - Silylation of functional groups, alkines and reactive aromatics
Simchen, Gerhard,Jonas, Simon
experimental part, p. 506 - 512 (2011/10/17)
The synthesis of trialkylsilyl-bis(trifluormethanesulfonyl)imides 3 is described. Compounds 3 with bulky trialkylsilyl groups 3a,b only exist in the silatautomeric form 3a′,b′ under usual conditions, 3c in the N-trimethylsilyl structure. Despite of the bulky silyl substituents in 3a′,b′ their reactivity is higher than that of trimethylsilyltriflate. Alcohols, carbonyl compounds, nitroalkanes and carboxylic acid esters are silylated in good yields, especially by the more reactive triisopropylsilyl derivative 3b′ in presence of tertiary amines, tert.-Butyl carboxylates and benzylcarboxylates are cleaved. Monosubstituted alkines and electron-rich (hetero) aromatics are carbosilylated in presence of N-ethyl-diisopropylamine.
