Extended Data Fig. 1: 19F NMR monitoring experiments for other Cu-mediated C − C coupling reactions.
From: Decoding the redox behaviour of copper in Ullmann-type coupling reactions
a, The time-course plot for the reaction between [(bpy)CuI(CF3)] (1a) and pentafluoroiodobenzene. b, The time-course plot for the reaction between [(bpy)CuI(CF3)] (1a) and 3,5-difluoro-4-iodobenzonitrile. c, The time-course plot for the reaction between [(bpy)CuI(CF3)] (1a) and 3-fluoro-2-iodobenzonitrile. d, The time-course plot for the reaction between [(bpy)CuI(CF3)] (1a) and methyl 4-iodobenzoate. e, The time-course plot for the reaction between [(bpy)CuI(CF3)] (1a) and iodobenzene. f, The time-course plot for the reaction between [(bpy)CuI(CF3)] (1a) and 1-bromo-2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzene (2-Br). g, The time-course plot for the reaction between [(bpy)CuI(C6F4-p-CF3)] (1c) and aryl iodide 2-I. Purple line, sum of observed fluorine signals, calculated as [CF3]total = [(bpy)Cu(CF3)] + 2 × [(bpy)Cu(CF3)2(Ar)] + [ArCF3] + 3 × [(bpy)Cu(CF3)3] + 4 × [Cu(CF3)4]− (for trifluoromethylation), or [CF3]total = [(bpy)Cu(ArF)] + [ArF − ArF] (for biaryl synthesis). N.D. = not detected.
