Optimization of reaction conditionsa.
Entry | Cat. | Solvent | Temp. (°C) | Yieldb (%) |
---|---|---|---|---|
1 | — | PhCl | 120 | 65 |
2 | Sm(OTf)3 | PhCl | 120 | 55 |
3c | Sm(OTf)3 | PhCl | 120 | 0 |
4 | Cs2CO3 | PhCl | 120 | 0 |
5 | Et3N | PhCl | 120 | 0 |
6 | AcOH | PhCl | 120 | 0 |
7 | — | Toluene | 120 | 35 |
8 | — | DMF | 120 | 63 |
9 | — | DMSO | 120 | 45 |
10 | — | 1,4-Dioxane | 120 | Trace |
11d | — | — | 120 | 73 |
12d | — | — | 110 | 75 |
13 d | — | — | 100 | 85 |
14d | — | — | 90 | 60 |
15d,e | — | — | 100 | 86 |
Reactions conditions: 1a (0.6 mmol), 2a (0.5 mmol), catalyst (10 mol% to 2a), solvent (1 mL), sealed tube, 10 h.
Isolated yield of pure product based on 2a.
Cs2CO3 as base was added to the reaction.
1a (1.5 mmol), 2a (0.5 mmol), sealed tube, 10 h.
Reaction time was 15 h.