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Fluorobis(phenylsulfonyl)methane: A Fluoromethide Equivalent and Palladium-Catalyzed Enantioselective Allylic Monofluoromethylation


  • This research was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (17350047, 17590087) and by Japan Science & Technology (JST) Agency, Innovation Plaza Tokai. T.F. is grateful for research fellowships from JSPS. We thank Dr. Jon Bordner, Shin-ichi Sakemi, and Dr. Masami Nakane, Pfizer Inc., for X-ray crystallographic analysis.


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Selective introduction of fluorine: Monofluoromethylation with the fluoromethide equivalent fluorobis(phenylsulfonyl)methane (1) was crucial in the syntheses of the pharmacologically important compounds monofluorinated (S)-ibuprofen ((S)-2) and 5-deoxy-5-fluoro-β-D-carbaribofuranose (3). The key step was a palladium-catalyzed allylic monofluoromethylation reaction.

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