Experimental evidencea,b.
| ||||||||
|---|---|---|---|---|---|---|---|---|
| Entry | F− | Solvent | Time | Yieldc (%) | ||||
| 2 | 11 | 10a | 12a | 13 | ||||
| 1 | TBAF | CD3OD | 17 h | 10 | 22 | 10 | 41 | 17 |
| 2 | TBAF | CD3CN/CD3OD (6.5 : 1) | 20 min | 36 | 23 | 21 | 15 | 5 |
| 3 | CsF | CD3CN/CD3OD (6.5 : 1) | 5 h | 7.8 | 51.5 | 4.2 | 34.9 | 1.6 |
| 4 | CsF | CD3CN/CD3OD (17.8 : 1) | 5 h | 34 | 38 | 12 | 15 | 1 |
| 5 | CsF | CD3CN/(CD3)3COD (6.5 : 1) | 5 h | 31.5 | 65.9 | — | — | 0 |
| 6 | CsF | CD3CN/(CD3)3COD (17.8 : 1) | 5 h | 65 | 35 | — | — | 0 |
All reactions were carried out on a 0.084 mmol reaction scale of triazolium precursor 1 in 0.75 mL of solvent in a sealed NMR tube. TBAF·3H2O or CsF (6 equiv.) was used as F− source.
Traces of 10b and 12b were detected by 19F NMR.
19F NMR yield.