title: Synthesis of azoimidazolium dyes with nitrous oxide.
abstract: A new method for the synthesis of industrially important azoimidazolium dyes is presented. The procedure is based on a reagent which is rarely used in the context of synthetic organic chemistry: nitrous oxide ("laughing gas"). N2O is first coupled to N-heterocyclic carbenes. Subsequent reaction with aromatic compounds through an AlCl3-induced C-H activation process provides azoimidazolium dyes in good yields.
authors.affiliation: Institut des Sciences et Ingénierie Chimiques, École Polytechnique Fédérale de Lausanne (EPFL).
authors.forename: Alexander G
authors.initials: AG
authors.lastname: Tskhovrebov
authors.forename: Lara C E
authors.initials: LC
authors.lastname: Naested
authors.forename: Euro
authors.initials: E
authors.lastname: Solari
authors.forename: Rosario
authors.initials: R
authors.lastname: Scopelliti
authors.forename: Kay
authors.initials: K
authors.lastname: Severin
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D008968:Molecular Conformation; D009609:Nitrous Oxide / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D004396:Coloring Agents; D006571:Heterocyclic Compounds; D007093:Imidazoles; C030011:carbene; C029899:imidazole; D009609:Nitrous Oxide; D008697:Methane
keywords: CH activation; azo coupling; carbenes; dyes; nitrous oxide