Table 1.
Conditions Explored for Reaction Optimizationa
| |||
|---|---|---|---|
| Entry | Additive | Yield of 1b | Yield of 1c |
| 1 | none | 14% | 18% |
| 2 | THF | 13% | 12% |
| 3 | 18-crown-6 | 3% | 2% |
| 4 | Ph3N | 9% | 13% |
| 5 | pyridine | 7% | 9% |
| 6 | 1,10-phen | 9% | 1% |
| 7 | HMPA | 9% | 8% |
| 8 | benzophenone | 32% | ND |
| 9 | benzophenoneb | 57% | 2% |
| 10 c | benzophenone | 72% | 2% |
Optimization was conducted on a 0.1 mmol scale. Yield was determined by 1H NMR using mesitylene internal standard.
0.25 equiv of benzophenone.
2.5 equiv of TEMPO+PF6−, 2.25 equiv of KHMDS, 0.45 equiv of benzophenone.