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18.15.1.2.3 Method 3: Trifluoromethylation of Arenes and Hetarenes

DOI: 10.1055/sos-SD-018-01314

Il'chenko, A. Y.Science of Synthesis, (2005181142.

Tetrahalomethanes are widely used in the syntheses of trifluoromethylated arenes and hetarenes.[‌62‌‌65‌] The iodo groups of iodoarenes are substituted upon interaction with trifluoroiodomethane (9) and copper in a polar aprotic solvent, giving (trifluoromethyl)arenes in good yields (Scheme 13).[‌49‌,‌66‌] Thus, (trifluoromethyl)benzene (22) is obtained in 74% yield when iodobenzene, trifluoroiodomethane (9), and copper in dimethylformamide are heated in a stainless-steel tube (Scheme 13).[‌66‌,‌67‌] Reaction of 1-iodo-2,3,5,6-tetramethylbenzene with trifluoroiodomethane (9) and copper in dimethylformamide at 150°C gives 2,3,5,6-tetramethyl-1-(trifluoromethyl)benzene in 65% yield.[‌68‌] 1-(Trifluoromethyl)naphthalene and 2-(trifluoromethyl)quinoline are also obtained in good yields by this method.[‌43‌,‌69‌]

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References