Table 1.
Optimization of reaction conditionsa.
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Entry | Oxidants | Equivalent | Temperature (°C) | Time (h) | Yield (%)b |
1 | – | – | 100 | 4.0 | N.R.c |
2 | K2S2O8 | 2.0 | 100 | 4.0 | N.R. |
3 | Ag2O | 2.0 | 100 | 4.0 | N.R. |
4 | CuO | 2.0 | 100 | 4.0 | N.R. |
5 | CuBr2 | 2.0 | 100 | 4.0 | 43 |
6 | CuBr2 | 4.0 | 100 | 4.0 | 95 |
7 | CuBr2 | 6.0 | 100 | 4.0 | 92 |
8 | CuBr2 | 4.0 | 100 | 2.0 | 94 |
9 | CuBr2 | 4.0 | 90 | 2.0 | 88 |
10 | CuBr2 | 4.0 | 80 | 2.0 | 57 |
11 | CuBr2 | 4.0 | 70 | 2.0 | N.R. |
12 | CuBr2 | 4.0 | 100 | 1.5 | 94 |
13 | CuBr2 | 4.0 | 100 | 1.0 | 89 |
14d | CuBr2 | 4.0 | 100 | 1.5 | 92 |
aUnless otherwise specified, all reactions were performed with 0.03 mmol of 1a in 10.0 mL of o-DCB under an argon atmosphere.
bIsolated yield.
cNo reaction.
dUnder an ambient environment.