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Published on: May 21, 2019
Nickel-Metallaphotoredox-Catalyzed Radical Cross-Couplings to Access α-Aryl-α-trifluoromethyl Amines Under Flow
Md Nuruzzaman Khan1,2, Jia-Yi Shou1, Feng-Ling Qing1
1State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
Abstract:
Herein, we report a method for the synthesis of α-aryl-α-trifluoromethyl amines via dual photoredox/nickel-catalysis between aryl bromides and N-trifluoroethyl hydroxylamine under flow conditions. This protocol enables the first direct 1-aminotrifluoroethylation of benzene derivatives under mild conditions in high yields (up to 84%) and with a wide functional group tolerance (32 examples). The transformation proceeds through photoinduced single-electron reduction of N-trifluoroethyl hydroxylamine, followed by 1,2-hydrogen atom transfer, to generate the α-aminotrifluoroethyl radical for cross-coupling of aryl bromides.
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