Table 1.
Optimization of Reaction Conditions
| |||||
|---|---|---|---|---|---|
| entry | reagent | solvent | T[°C] | time [h] |
yield[%]b |
| 1 | 2a | CHCl3 | 70 | 6 | 0c |
| 2 | 2b | CHCl3 | 70 | 6 | 14 |
| 3 | 2b | CHCl3 | 90 | 6 | 45 |
| 4 | 2b | CHCl3 | 90 | 12 | 70 |
| 5 | 2b | PhCH3 | 90 | 12 | 27 |
| 6 | 2b | PhCF3 | 90 | 12 | 50 |
| 7 | 2b | CH3CN | 90 | 12 | 13 |
| 8 | 2b | DCE | 90 | 12 | 73 (68)d |
| 9 | 2b e | DCE | 90 | 12 | 68 |
| 10 | 2c | DCE | 90 | 12 | 41 |
| 11 | 2d | DCE | 90 | 12 | 14 |
| 12 | 2b f | DCE | 90 | 12 | 39 |
Conditions: 0.1 mmol 1i, 0.1 mmol 2, 0.5 mL solvent (0.2 M).
Yield determined by 1H NMR using 1,1,2,2-tetrachloroethane as the internal standard.
No reaction.
Isolated yield from 0.2 mmol scale reaction.
Using 2b stored in the desiccator for 1 month and DCE stored on the benchtop.
0.02 mmol (20 mol %) 2b used.