title: Iron-Catalyzed Reaction of Urea with Alcohols and Amines: A Safe Alternative for the Synthesis of Primary Carbamates.
abstract: A general study of the iron-catalyzed reaction of urea with nucleophiles is here presented. The carbamoylation of alcohols allows for the synthesis of N-unsubstituted (primary) carbamates, including present drugs (Felbamate and Meprobamate), without the necessity to apply phosgene and related derivatives. Using amines as nucleophiles gave rise to the respective mono- and disubstituted ureas via selective transamidation reaction. These atom-economical transformations provide a direct and selective access to valuable compounds from cheap and readily available urea using a simple Lewis-acidic iron(II) catalyst.
authors.affiliation: Leibniz-Institut für Katalyse e.V. an der, Universität Rostock, Albert-Einstein-Straße 29a, 18059, Rostock, Germany.
authors.forename: Miguel
authors.initials: M
authors.lastname: Peña-López
authors.affiliation: Leibniz-Institut für Katalyse e.V. an der, Universität Rostock, Albert-Einstein-Straße 29a, 18059, Rostock, Germany.
authors.forename: Helfried
authors.initials: H
authors.lastname: Neumann
authors.affiliation: Leibniz-Institut für Katalyse e.V. an der, Universität Rostock, Albert-Einstein-Straße 29a, 18059, Rostock, Germany. Matthias.Beller@catalysis.de.
authors.forename: Matthias
authors.identifier: 0000-0001-5709-0965
authors.initials: M
authors.lastname: Beller
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D055772:Green Chemistry Technology; D007501:Iron / Q000737:chemistry*; D012449:Safety; D014508:Urea / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000588:Amines; D002219:Carbamates; D014508:Urea; D007501:Iron
keywords: catalysis; iron; nucleophilic substitution; primary carbamates; urea