The acetonitrile-solvated [(MeCN)Ni(C F ) ] was prepared in order to compare and contrast its reactivity with the known [(MeCN)Ni(CF ) ] towards organic electrophiles. Both [(MeCN)Ni(CF ) ] and [(MeCN)Ni(C F ) ] successfully react with aryl iodonium and diazonium salts as well as alkynyl iodonium salts to give fluoroalkylated organic products. Electrochemical analysis of [(MeCN)Ni (C F ) ] suggests that, upon electro-oxidation to [(MeCN) Ni (C F ) ], reductive homolysis of a perfluoroethyl radical occurs, with the concomitant formation of [(MeCN) Ni (C F ) ]. Catalytic C-H trifluoromethylations of electron-rich arenes were successfully achieved using either [(MeCN)Ni(CF ) ] or the related [Ni(CF ) ] . Stoichiometric reactions of the solvated nickel complexes reveal that "ligandless" nickel is exceptionally capable of serving as reservoir of CF groups under catalytically relevant conditions.
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