Table 1. Optimization of reaction parameters.
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Entry | CF3 source | Catalyst | Additive | Yield a (%) |
1 | I | — | — | 7 |
2 | II | — | — | 33, 21 b |
3 | III | — | — | 12, 7 b |
4 | II | — | TFA (2 equiv.) | 76, 62 c |
5 | II | — | TFA (1 equiv.) | 69 |
6 | III | — | TFA (2 equiv.) | 13 |
7 d | II | — | TFA (2 equiv.) | 59 |
8 | II | A (5 mol%) | — | 21 |
9 | II | A (100 mol%) | B (1 equiv.) | 33 |
10 e | II | C (5 mol%) | — | 20 |
11 e | II | D (2 mol%) | — | 31 |
12 e | III | C (5 mol%) | — | 40 |
13 e | III | D (2 mol%) | — | 38 |
a Determined by 19F NMR integration relative to an internal standard (C6H5CF3).
b Reaction at 60 °C.
c Reaction time is 1 h.
d Reaction in CH3CN.
e 14 W bulb as light source (λ max = 452 nm). A = Cu(CH3CN)4PF6. B = 1,10-phenantroline. C = Ru(bpy)3(PF6)2. D = methylene blue. TFA = trifluoroacetic acid.