title: A One-Pot Synthesis of N-Aryl-2-Oxazolidinones and Cyclic Urethanes by the Lewis Base Catalyzed Fixation of Carbon Dioxide into Anilines and Bromoalkanes.
abstract: The multicomponent assembly of pharmaceutically relevant N-aryl-oxazolidinones through the direct insertion of carbon dioxide into readily available anilines and dibromoalkanes is described. The addition of catalytic amounts of an organosuperbase such as Barton's base enables this transformation to proceed with high yields and exquisite substrate functional-group tolerance under ambient CO2 pressure and mild temperature. This report also provides the first proof-of-principle for the single-operation synthesis of elusive seven-membered ring cyclic urethanes.
authors.affiliation: Department of Chemistry, P.O. Box 55, 00014, University of Helsinki, Finland.
authors.forename: Teemu
authors.initials: T
authors.lastname: Niemi
authors.affiliation: Department of Chemistry, P.O. Box 55, 00014, University of Helsinki, Finland. timo.repo@helsinki.fi.
authors.forename: Jesus E
authors.identifier: http://orcid.org/0000-0003-0028-1271
authors.initials: JE
authors.lastname: Perea-Buceta
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria, 28040, Madrid, Spain. israel@quim.ucm.es.
authors.forename: Israel
authors.identifier: http://orcid.org/0000-0002-0186-9774
authors.initials: I
authors.lastname: Fernández
authors.affiliation: Department of Chemistry, P.O. Box 55, 00014, University of Helsinki, Finland.
authors.forename: Otto-Matti
authors.initials: OM
authors.lastname: Hiltunen
authors.affiliation: Department of Chemistry, P.O. Box 55, 00014, University of Helsinki, Finland.
authors.forename: Vili
authors.initials: V
authors.lastname: Salo
authors.affiliation: Department of Chemistry, P.O. Box 55, 00014, University of Helsinki, Finland.
authors.forename: Sari
authors.initials: S
authors.lastname: Rautiainen
authors.affiliation: Department of Chemistry, P.O. Box 55, 00014, University of Helsinki, Finland.
authors.forename: Minna T
authors.initials: MT
authors.lastname: Räisänen
authors.affiliation: Department of Chemistry, P.O. Box 55, 00014, University of Helsinki, Finland. jesus.pereabuceta@helsinki.fi.
authors.forename: Timo
authors.identifier: http://orcid.org/0000-0002-3116-6199
authors.initials: T
authors.lastname: Repo
keywords: 2-oxazolidinones; antibiotics; carbon dioxide; density functional calculations; guanidine superbases