Superelectrophilic chemistry of imidazoles

MR Sheets, A Li, EA Bower, AR Weigel…

Index: Sheets, Matthew R.; Li, Ang; Bower, Edward A.; Weigel, Andrew R.; Abbott, Matthew P.; Gallo, Robert M.; Mitton, Adam A.; Klumpp, Douglas A. Journal of Organic Chemistry, 2009 , vol. 74, # 6 p. 2502 - 2507

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Citation Number: 18

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- ...