A polymeric ionic liquid catalyst for the N-formylation and N-methylation of amines using CO2/PhSiH3
Aswin Gopakumar, Loris Lombardo, Zhaofu Fei, Serhii Shyshkanov, Dmitry Vasilyev, Arunraj Chidambaram, Kyriakos C. Stylianou, Andreas Züttel, Paul J. Dyson
Abstract
We describe a polymeric ionic liquid (PIL) derived from trimethyl(p-vinylbenzyl)ammonium chloride ([VBTAm]Cl) that efficiently catalyzes the N-formylation of amines employing CO2 and PhSiH3 at room temperature with low catalyst loadings in near-quantitative yield. Under more forcing conditions N-methylated products can be selectively obtained. The PIL catalyst can be easily recovered and reused repeatedly without a decrease in activity. The reaction mechanism was studied in situ using high-pressure NMR spectroscopy and a tentative mechanistic cycle has been proposed.
Topics & Concepts
FormylationIonic liquidCatalysisChemistryYield (engineering)Ammonium chlorideChlorideOrganic chemistryInorganic chemistryPolymer chemistryMaterials scienceMetallurgyCarbon dioxide utilization in catalysisAsymmetric Hydrogenation and CatalysisCO2 Reduction Techniques and Catalysts