title: A synthetic approach to N-aryl carbamates via copper-catalyzed Chan-Lam coupling at room temperature.
abstract: A mild and efficient synthesis of N-arylcarbamates was achieved by reacting azidoformates with boronic acids in the presence of 10 mol % of copper chloride catalyst. The reaction proceeds readily in an open flask at room temperature without additional base, ligand, or additive. Rapid access to urea analogues via a two-step one-pot procedure is enabled by reacting N-arylcarbamates with aluminum-amine complexes. In addition, among several boronic acid derivatives prepared, dimethylphenyl boronate was found to react rapidly in its reaction with benzyl azidoformate, invoking in situ generation of this species in the catalytic cycle.
authors.affiliation: Department of Chemistry and Nano Science, Ewha Womans University , Seoul 120-750, South Korea.
authors.forename: Soo-Yeon
authors.initials: SY
authors.lastname: Moon
authors.forename: U Bin
authors.initials: UB
authors.lastname: Kim
authors.forename: Dan-Bi
authors.initials: DB
authors.lastname: Sung
authors.forename: Won-Suk
authors.initials: WS
authors.lastname: Kim
mesh_terms: D001386:Azides / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013696:Temperature
chemical_list: D001386:Azides; D001897:Boronic Acids; D002219:Carbamates; D008024:Ligands; D003300:Copper