Superacid-Promoted Reactions of Pyrazole­-carboxaldehydes and the Role of Dicationic Electrophiles

doi:10.1055/s-2005-865374

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Synfacts 2005(0): 0027-0027
DOI: 10.1055/s-2005-865374

Synthesis of Heterocycles

Superacid-Promoted Reactions of Pyrazole-carboxaldehydes and the Role of Dicationic Electrophiles

Contributor(s): Victor Snieckus, Zhongdong Zhao
D. A. Klumpp*, P. J. Kindelin, A. Li
Northern Illinois University, DeKalb, USA

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Publication History

Publication Date:
20 July 2005 (online)

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Significance

Treatment of pyrazolecarboxaldehydes with super acids leads to the formation of dicationic species which are highly reactive for electrophilic diarylation even with weakly nucleophilic arenes. Thus a variety of substituted pyrazolecarboxaldehydes condense with benzene to provide side-chain substituted products. The mechanism involving a dicationic intermediate is supported by low temperature ¹³C NMR studies.