N-Silylation of amines mediated by Et3SiH/KOtBu
Palumbo, Fabrizio and Rohrbach, Simon and Tuttle, Tell and Murphy, John A. (2019) N-Silylation of amines mediated by Et3SiH/KOtBu. Helvetica Chimica Acta, 102 (12). pp. 1-8. e1900235. ISSN 0018-019X (https://doi.org/10.1002/hlca.201900235)
Preview |
Text.
Filename: Palumbo_etal_HCA_2019_N_Silylation_of_amines_mediated_by_Et3SiH_KOtBu.pdf
Accepted Author Manuscript Download (774kB)| Preview |
Abstract
Silylation of primary and secondary amines is reported, using triethylsilane as the silylating reagent in the presence of potassium tert-butoxide (KOtBu). The reaction proceeds well in the presence of 0.2 equiv of KOtBu. In competition experiments, aniline is selectively silylated over aliphatic amines. Computational studies support a catalytic mechanism which is initiated by KOtBu interacting with the silane to form KH and silylated amine. The KH then takes over the role of base in the propagation of the cyclic mechanism, and deprotonates the amine. This reacts with R3SiH to afford the product R3SiNR’R” and regenerate KH.
-
-
Item type: Article ID code: 70226 Dates: DateEvent1 December 2019Published25 October 2019Published Online21 October 2019AcceptedNotes: © 2019 Wiley-VHCAAG,Zurich,Switzerland F. Palumbo, S. Rohrbach, T. Tuttle, J. A. Murphy, HCA 2019, 102, e1900235. Subjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Technology and Innovation Centre > BionanotechnologyDepositing user: Pure Administrator Date deposited: 22 Oct 2019 13:41 Last modified: 31 Aug 2024 01:02 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/70226