title: Functional-Group-Tolerant, Silver-Catalyzed N-N Bond Formation by Nitrene Transfer to Amines.
abstract: Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI═NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiary amines but also to complex natural molecules such as brucine or quinine, where the products derived from N-N bond formation were exclusively formed. Theoretical mechanistic studies have shown that this selective N-amidation reaction proceeds through triplet silver nitrenes.
authors.affiliation: Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva , 21007 Huelva, Spain.
authors.forename: Lourdes
authors.initials: L
authors.lastname: Maestre
authors.affiliation: Institute of Chemical Research of Catalonia, ICIQ, The Barcelona Institute of Science and Technology , Avgda. Països Catalans, 16, 43007 Tarragona, Spain.
authors.forename: Ruth
authors.initials: R
authors.lastname: Dorel
authors.affiliation: Institute of Chemical Research of Catalonia, ICIQ, The Barcelona Institute of Science and Technology , Avgda. Països Catalans, 16, 43007 Tarragona, Spain.
authors.forename: Óscar
authors.initials: Ó
authors.lastname: Pablo
authors.affiliation: Institute of Chemical Research of Catalonia, ICIQ, The Barcelona Institute of Science and Technology , Avgda. Països Catalans, 16, 43007 Tarragona, Spain.
authors.forename: Imma
authors.initials: I
authors.lastname: Escofet
authors.affiliation: Institute of Chemical Research of Catalonia, ICIQ, The Barcelona Institute of Science and Technology , Avgda. Països Catalans, 16, 43007 Tarragona, Spain.|Department of Chemistry, Faculty of Science, Hokkaido University , North-10 West-8 Kita-ku, Sapporo, Hokkaido 060-0810, Japan.
authors.forename: W M C
authors.initials: WM
authors.lastname: Sameera
authors.affiliation: Instituto de Investigaciones Químicas, Centro de Investigaciones Científicas Isla de la Cartuja, CSIC , Avenida Américo Vespucio 49, 41092 Sevilla, Spain.
authors.forename: Eleuterio
authors.identifier: 0000-0002-8378-8459
authors.initials: E
authors.lastname: Álvarez
authors.affiliation: Institute of Chemical Research of Catalonia, ICIQ, The Barcelona Institute of Science and Technology , Avgda. Països Catalans, 16, 43007 Tarragona, Spain.|Departament de Química, Universitat Autònoma de Barcelona , 08193 Bellaterra, Spain.
authors.forename: Feliu
authors.identifier: 0000-0001-8806-2019
authors.initials: F
authors.lastname: Maseras
authors.affiliation: Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva , 21007 Huelva, Spain.
authors.forename: M Mar
authors.initials: MM
authors.lastname: Díaz-Requejo
authors.affiliation: Institute of Chemical Research of Catalonia, ICIQ, The Barcelona Institute of Science and Technology , Avgda. Països Catalans, 16, 43007 Tarragona, Spain.|Departament de Química Orgànica i Analítica, Universitat Rovira i Virgili , C/Marcel·lí Domingo s/n, 43007 Tarragona, Spain.
authors.forename: Antonio M
authors.identifier: 0000-0001-6808-3007
authors.initials: AM
authors.lastname: Echavarren
authors.affiliation: Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva , 21007 Huelva, Spain.
authors.forename: Pedro J
authors.identifier: 0000-0002-6899-4641
authors.initials: PJ
authors.lastname: Pérez