title: Synthesis of an N-mesityl substituted chiral imidazolium salt for NHC-catalyzed reactions.
abstract: A new synthetic approach to chiral imidazolium salts makes possible the first synthesis of an N-mesityl substituted, aminoindanol-derived N-heterocyclic carbene precursor, 1.ClO4. The successful synthesis allows the first direct comparison of otherwise identical imidazolium and triazolium precursors across a number of NHC-catalyzed processes. These studies confirm striking differences in reactivity and mechanism between the two classes.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6232, USA.
authors.forename: Justin R
authors.initials: JR
authors.lastname: Struble
authors.forename: Juthanat
authors.initials: J
authors.lastname: Kaeobamrung
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode
mesh_terms: D002384:Catalysis; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D012492:Salts; D013237:Stereoisomerism
chemical_list: D007093:Imidazoles; D007202:Indicators and Reagents; D012492:Salts