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.