Table 1. Lewis Acid Optimizationa.
| entry | Lewis acid | solvent | yield (%)b |
|---|---|---|---|
| 1 | none | t-amylOH | nr |
| 2 | Ca(NTf2)2 | t-amylOH | >99 |
| 3 | Ca(OTf)2 | t-amylOH | 10 |
| 4 | Mg(NTf2)2 | t-amylOH | 50 |
| 5 | Ba(NTf2)2 | t-amylOH | 72 |
| 6 | Li(NTf2) | t-amylOH | 13 |
| 7 | Zn(NTf2)2 | t-amylOH | 3 |
| 8 | B(C6F5)3 | t-amylOH | 3 |
| 9 | Ca(NTf2)2 | t-BuOH | 76 |
| 10 | Ca(NTf2)2 | CH3CN | 55 |
| 11 | Ca(NTf2)2 | toluene | 53 |
Reaction conditions: sulfonimidoyl fluoride (1 equiv), aniline (2 equiv), Lewis acid (1 equiv), t-amylOH (0.2 M), 80 °C, and 5 h.
Yield was determined by HPLC.
