title: A Metal-Free Synthesis of N-Aryl Carbamates under Ambient Conditions.
abstract: The first chemo- and site-selective process for the formation of N-aryl-carbamates from cyclic organic carbonates and aromatic amines is reported. The reactions proceed smoothly under extremely mild reaction conditions using TBD (triazabicyclodecene) as an effective and cheap organocatalyst, thus providing a sustainable and new methodology for the formation of a wide variety of useful N-aryl carbamate synthons in good to excellent yields. Computational investigations have been performed and show the underlying reason for the observed unique reactivity as related to an effective proton-relay mechanism mediated by the bicyclic guanidine base.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain).
authors.forename: Wusheng
authors.initials: W
authors.lastname: Guo
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain).
authors.forename: Joan
authors.initials: J
authors.lastname: Gónzalez-Fabra
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain).
authors.forename: Nuno A G
authors.initials: NA
authors.lastname: Bandeira
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain).|Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Marcel lí Domingo s/n, 43007 Tarragona (Spain).
authors.forename: Carles
authors.initials: C
authors.lastname: Bo
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain). akleij@iciq.es.|Catalan Institute of Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona (Spain). akleij@iciq.es.
authors.forename: Arjan W
authors.initials: AW
authors.lastname: Kleij
keywords: N-aryl carbamates; anilines; cyclic carbonates; hydrogen bonds; organocatalysis