Table 1.
Optimization of the reaction conditiona
| Entry | Catalyst | Loading | Solvent | T (°C) | 1H-NMR yield |
|---|---|---|---|---|---|
| 1 | Re2O7 | 2% | DCE | 100 | 30% |
| 2 | HReO4 | 4% | DCE | 100 | 24% |
| 3 | MeReO3(MTO) | 2% | DCE | 100 | NR |
| 4 | (CO)5ReBr | 2% | DCE | 100 | NR |
| 5 | Re(CO)10 | 2% | DCE | 100 | NR |
| 6 | Fe(OTf)3 | 2% | DCE | 100 | Trace |
| 7 | CuCl2 | 2% | DCE | 100 | NR |
| 8 | AlCl3 | 2% | DCE | 100 | NR |
| 9 | FeCl3 | 2% | DCE | 100 | NR |
| 10 | V2O5 | 2% | DCE | 100 | NR |
| 11 | Re2O7 | 2% | CF3CH2OH | 100 | 54% |
| 12 | Re2O7 | 2% | HFIP | 100 | 86% (85%)b |
| 13 | Re2O7 | 1% | HFIP | 100 | 70% |
| 14 | Re2O7 | 2% | HFIP | 80 | 69% |
| 15 | Fe(OTf)3 | 2% | HFIP | 100 | 67% |
aReactions were performed with 1a (1.0 equiv.), solvent (0.2 M), catalyst (1–5 mol%) at 100 °C for 12 hours. bisolated yield.