Optimization of the reaction conditionsa.
Entry | Catalyst | Temperature (°C) | Solvent | Yieldb (%) |
---|---|---|---|---|
1 | — | 150 | Toluene | 18 |
2 | — | 150 | Water | 16 |
3 | — | 150 | — | 63 |
4 | AgOTf | 150 | Toluene | 84 |
5 | Cu(OTf)2 | 150 | Toluene | 87 |
6 | Sc(OTf)3 | 150 | Toluene | 50 |
7 | AlCl3 | 150 | Toluene | 49 |
8 | TfOH | 150 | Toluene | 90 |
9 | TMSOTf | 150 | Toluene | Quant. |
10 | TMSOTf | 150 | DCM | 93 |
11 | TMSOTf | 150 | MeCN | Quant. |
12 | TMSOTf | 150 | — | 96 |
13 | TMSOTf | 100 | — | 92 |
14 | TMSOTf | 25 | — | 47 |
15 | TMSOTf | 200 | — | 75 |
Reaction conditions: 1a (0.48 mmol, 1.0 equiv.), 2a (0.95 mmol, 2.0 equiv.), HMDS (2.38 mmol, 5.0 equiv.), catalyst (0.048 mmol, 0.1 equiv.).
Isolated yields.