title: Palladium-catalyzed N-acylation of monosubstituted ureas using near-stoichiometric carbon monoxide.
abstract: The palladium-catalyzed carbonylation of urea derivatives with aryl iodides and bromides afforded N-benzoyl ureas (20 examples) in yields attaining quantitative via the application of near-stoichiometric amounts of carbon monoxide generated from the decarbonylation of the CO precursor, 9-methylfluorene-9-carbonyl chloride. The synthetic protocol displayed good functional group tolerance. The methodology is also highly suitable for (13)C isotope labeling, which was demonstrated through the synthesis of three benzoyl ureas, including the insecticide triflumuron, whereby (13)CO was incorporated into the core structure.
authors.affiliation: Center for Insoluble Protein Structures, Department of Chemistry and Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
authors.forename: Klaus
authors.initials: K
authors.lastname: Bjerglund
authors.forename: Anders T
authors.initials: AT
authors.lastname: Lindhardt
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D000215:Acylation; D001549:Benzamides / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D001549:Benzamides; C023957:triflumuron; D010165:Palladium; D002248:Carbon Monoxide; D014508:Urea