Superelectrophilic chemistry of imidazoles.
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.
Sheets
Matthew R
MR
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
Li
Ang
A
Bower
Edward A
EA
Weigel
Andrew R
AR
Abbott
Matthew P
MP
Gallo
Robert M
RM
Mitton
Adam A
AA
Klumpp
Douglas A
DA