Table 1.
entry | additive | equiv 6 | temp | time | yieldb |
---|---|---|---|---|---|
1 | none | 4 | 23 °C | 12 h | 60% |
2 | NaBF4 | 4 | 23 °C | 12 h | 68% |
3 | NaHCO3 | 4 | 23 °C | 12 h | 70% |
4 | HCO2H | 4 | 23 °C | 12 h | 50% |
5 | CF3CO2H | 4 | 23 °C | 12 h | 88% |
6 | TsOH | 4 | 23 °C | 12 h | 38% |
7 | CF3CO2H | 2 | 23 °C | 12 h | 98% |
8 | CF3CO2H | 2 | 50 °C | 5 h | 96% |
9 | none | 2 | 50 °C | 5 h | 28% |
10c | CF3CO2H | 2 | 50 °C | 5 h | 0% |
11d | CF3CO2H | 2 | 50 °C | 5 h | 0% |
Unless otherwise noted, reactions were conducted using 2 mol% Ru(bpy)3Cl2 and 1 equiv of additive in degassed MeCN (0.25 M) and were irradiated using a 23 W compact fluorescent light bulb at a distance of 30 cm.
Yields determined by 1H NMR using an internal standard.
Reaction conducted in the absence of Ru(bpy)3Cl2.
Reaction conducted in the dark.