We disclose an efficient one-pot transformation of trifluorodiazoethane and higher perfluorinated homologues with various nitroolefins. This method takes advantage of the nitro group as a traceless activating and directing group (TADG) that is released in the aromatization step to produce 4-substituted 3-perfluoroalkyl pyrazoles with complete regioselectivity. The potential of this method is further demonstrated by the synthesis of penthiopyrad.
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Chen et al. (2017) studied this question.
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