title: Superelectrophilic chemistry of imidazoles.
abstract: The mechanistic and synthetic chemistry of imidazole-based superelectrophiles has been studied. The protonated imidazole ring, or imidazolium group, is shown to enhance the electrophilic reactivity of an adjacent carboxonium group (compared to a related monocationic species). This leads to efficient condensation reactions between imidazole aldehydes and ketone with arenes in the Brønsted superacid CF3SO3H. The imidazole-based superelectrophiles are shown to be useful in other reactions leading to functionalized heterocycles. The imidazolium group may also trigger charge migration reactions in dicationic species.
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Sheets
authors.forename: Ang
authors.initials: A
authors.lastname: Li
authors.forename: Edward A
authors.initials: EA
authors.lastname: Bower
authors.forename: Andrew R
authors.initials: AR
authors.lastname: Weigel
authors.forename: Matthew P
authors.initials: MP
authors.lastname: Abbott
authors.forename: Robert M
authors.initials: RM
authors.lastname: Gallo
authors.forename: Adam A
authors.initials: AA
authors.lastname: Mitton
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp