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. 2023 Jul 25;25(30):5666–5670. doi: 10.1021/acs.orglett.3c02132

Table 1. Lewis Acid Optimizationa.

graphic file with name ol3c02132_0005.jpg

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
a

Reaction conditions: sulfonimidoyl fluoride (1 equiv), aniline (2 equiv), Lewis acid (1 equiv), t-amylOH (0.2 M), 80 °C, and 5 h.

b

Yield was determined by HPLC.