Copper-Catalyzed Remote C(sp3 )-H Trifluoromethylation of Carboxamides and Sulfonamides.
Zhonglin LiuHaiwen XiaoBenxiang ZhangHaigen ShenLin ZhuChaozhong LiPublished in: Angewandte Chemie (International ed. in English) (2019)
Reported herein is an unprecedented protocol for trifluoromethylation of unactivated aliphatic C(sp3 )-H bonds. With Cu(OTf)2 as the catalyst, the reaction of N-fluoro-substituted carboxamides (or sulfonamides) with Zn(CF3 )2 complexes provides the corresponding δ-trifluoromethylated carboxamides (or sulfonamides) in satisfactory yields under mild reaction conditions. A radical mechanism involving 1,5-hydrogen atom transfer of N-radicals followed by CF3 -transfer from CuII -CF3 complexes to the thus formed alkyl radicals is proposed.
Keyphrases
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