Activation of TMSCN by N-Heterocyclic Carbenes for Facile Cyanosilylation of Carbonyl Compounds
The Journal of Organic Chemistry2006Vol. 71(3), pp. 1273–1276
Citations Over TimeTop 1% of 2006 papers
Abstract
N-Heterocyclic carbenes were found to be highly effective organocatalysts in activating TMSCN for facile cyanosilylation of carbonyl compounds. Cyano transfer from TMSCN to aldehydes and ketones proceeds at room temperature in the presence of only 0.01-0.5 mol % of N-heterocyclic carbene (1), leading to a range of trimethylsilylated cyanohydrins in very good to excellent yields. These conditions are extremely mild and simple and tolerate various functional groups.
Related Papers
- → Complexes with protic (NH,NH and NH,NR) N-heterocyclic carbene ligands(2015)118 cited
- → Dinuclear N-heterocyclic carbene copper(I) complexes(2017)37 cited
- → Chemistry of small rings. 20. Reactions of azirines. Carbene and carbenoid reactions(1973)46 cited
- → Dicationic ditelluride salts stabilized by N-heterocyclic carbene(2019)8 cited
- → ChemInform Abstract: Preparation, Structure, and Chemistry of (O‐Acyl imidato)‐ and (O‐Alkyl imidato)carbene Pentacarbonyl Complexes of Chromium.(1989)