Superelectrophilic Chemistry of Imidazoles

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• 作者：Matthew R. Sheets ; Ang Li ; Edward A. Bower ; Andrew R. Weigel ; Matthew P. Abbott ; Robert M. Gallo ; Adam A. Mitton ; Douglas A. Klumpp*
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：March 20, 2009
• 年：2009
• 卷：74
• 期：6
• 页码：2502-2507
• 全文大小：220K
• 年卷期：v.74,no.6(March 20, 2009)
• ISSN：1520-6904

文摘

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.