Preparation of Carbamates, Esters, Amides, and Unsymmetrical Ureas via Brønsted Acid-Activated <i>N</i>-Acyl Imidazoliums
Rebecca B. Watson, Todd W. Butler, Jacob C. DeForest
Abstract
We report the application of Brønsted acid–activated N-acyl imidazoliums as versatile intermediates in carbonyl transformations. The efficient and scalable procedure was validated on a diverse set of carbamates, esters, amides, and unsymmetrical ureas (21 examples, up to 91% yield). Additionally, we exemplify this method on multikilogram scale for the synthesis of an electron-deficient carbamate.
Topics & Concepts
Yield (engineering)ChemistryBrønsted–Lowry acid–base theoryCarbamateAmideOrganic chemistryCombinatorial chemistryCatalysisMetallurgyMaterials scienceAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisCarbon dioxide utilization in catalysis