Table 2 Deoxytrifluoromethylation/aromatization of both activated/non-activated substrates
| ||||
|---|---|---|---|---|
Entry | R | Operation | Conditions (Aromatization) | Yield (19F NMR) |
2.1 | tBu | Isolation | NBS (1.1 equiv.) 10% AIBN o-DCB (0.2 M) 120 °C, 14 h | 49% |
2.2 | tBu | Isolation | NBS (3 equiv.) 10% AIBN o-DCB (0.2 M) 120 °C, 14 h | 96% |
2.3 | tBu | No Silica Filter | NBS (3 equiv.) 10% AIBN THF (0.2 M) 65 °C, 14 h | 0% |
2.4 | tBu | No Silica Filter/Solvent Change | NBS (3 equiv.) 10% AIBN o-DCB (0.2 M) 120 °C, 14 h | 0% |
2.5 (Conditions B) | tBu | Silica Filter/Solvent Change | NBS (2 equiv.) 10% AIBN o-DCB (0.2 M) 120 °C, 14 h | 82% |
2.6 | Ph | Silica Filter/Solvent Change | NBS (2 equiv.) 10% AIBN o-DCB (0.2 M) 120 °C, 14 h | 81% |
2.7 (Conditions C) | Ph | Silica Filter/Solvent Change | DDQ (3 equiv.) o-DCB (0.2 M) 120 °C, 14 h | 92% |
