Addition of N-heterocyclic carbenes to imines: phenoxide assisted deprotonation of an imidazolium moiety and generation of breslow intermediates derived from imines.
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.
Simonovic
Stevan
S
Department of Chemistry, University of York, Heslington, York, YO10 5DD, United Kingdom.
Frison
Jean-Cédric
JC
Koyuncu
Hasan
H
Whitwood
Adrian C
AC
Douthwaite
Richard E
RE
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
D006571:Heterocyclic Compounds; D007093:Imidazoles; D007097:Imines; D010087:Oxides; D011522:Protons; C030011:carbene; D008697:Methane