title: Addition of N-heterocyclic carbenes to imines: phenoxide assisted deprotonation of an imidazolium moiety and generation of breslow intermediates derived from imines.
abstract: Reactions between imidazolium-imine salts and base result in C-C bond formation via intermediate N-heterocyclic carbenes. In the presence of a proximal OH moiety, carbene formation occurs via intramolecular deprotonation by phenoxide. For simple imines, a reactive Breslow-type intermediate gives access to new heterocycles with the formation of six- and seven-member rings.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, YO10 5DD, United Kingdom.
authors.forename: Stevan
authors.initials: S
authors.lastname: Simonovic
authors.forename: Jean-Cédric
authors.initials: JC
authors.lastname: Frison
authors.forename: Hasan
authors.initials: H
authors.lastname: Koyuncu
authors.forename: Adrian C
authors.initials: AC
authors.lastname: Whitwood
authors.forename: Richard E
authors.initials: RE
authors.lastname: Douthwaite
mesh_terms: D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*; D011522:Protons; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D007093:Imidazoles; D007097:Imines; D010087:Oxides; D011522:Protons; C030011:carbene; D008697:Methane