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Yu-Dong Yang, Xu Lu, Guokai Liu, Etsuko Tokunaga, Dr. Seiji Tsuzuki and Prof. Norio Shibata Cation versus Radical: Studies on the C/O Regioselectivity in Electrophilic Tri-, Di- and Monofluoromethylations of β-Ketoesters ChemistryOpen 1

Article first published online: 11 OCT 2012 | DOI: 10.1002/open.201200032

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Fluoromethylation. The C/O regioselectivity of β-ketoesters with fluorinated methylsulfoxinium salts 2 is discussed. Trifluoromethylation involves the formation of a more cationic species represented by +CF3 to provide C-alkylated products, while monofluoromethylation possibly proceeds involving a more radical-like species such as .CFH2 to give O-alkylated species. Difluoromethylation could involve both cationic and radical species, which afford a mixture of C and O isomers.

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