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ortho-Allylation of 1-Arylpyrazoles via Iron-Catalyzed C-H Bond Activation

Nakamura et al. have reported an ortho-allylation of 1-arylpyrazoles with allyl phenyl ethers via iron-catalyzed C-H bond activation. In the presence of Fe(acac)3 / 4,4'-di-tert-butyl-2,2'-bipyridyl (abbrev.: dtbpy) and in situ prepared diphenyl zinc, the reaction proceeds at 0 ºC to afford the ortho-allylated product. In this reaction, no allylated products are obtained without using the iron catalyst and also, no deuterated products are obtained after treatment with D2O instead of allyl phenyl ethers. On the other hand, in the presence of the iron catalyst, a deuteration at the ortho-position of 1-arylpyrazoles is performed by the treatment with D2O. These results suggest that this allylation proceeds via the possible formation of an iron-intermediate generated by iron-catalyzed C-H bond activation.

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