One-Pot Oxidative Amidation of Aldehydes via the Generation of Nitrile Imine Intermediates
Martyn C. Henry, Laura Minty, Alexander C. W. Kwok, J Mark Elwood, Adam J. Foulis, Jonathan Pettinger, Craig Jamieson
Abstract
High Resolution Image Download MS PowerPoint Slide A one-pot procedure for the oxidative amidation of aldehydes via the in situ generation of reactive nitrile imine (NI) intermediates has been developed. Distinct from our progenitor processes, mechanistic and control experiments revealed that the NI undergoes rapid oxidation to an acyl diazene species, which then facilitates N -acylation of an amine. A range of substrates have been explored, including application in the synthesis of pharmaceutically relevant compounds.
Topics & Concepts
ChemistryNitrileImineAcylationAmine gas treatingOxidative phosphorylationOrganic chemistryCombinatorial chemistryCatalysisBiochemistryChemical Synthesis and AnalysisSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis