TABLE 1. Optimizing Reaction Conditions.
entry | CuX | solventa | conversion (%)b |
---|---|---|---|
1 | CuCN | CH2CI2 | 24 |
2 | CuOAc | CH2CI2 | <5 |
3 | Cu(OTf)2 | CH2CI2 | 0 |
4 | Cu(BF4)2 | CH2CI2 | 15 |
5 | Cu(NO3)2 | CH2CI2 | 0 |
6 | Cu(CIO4)2 | CH2CI2 | 22 |
7 | Cu(CF3COO)2 | CH2CI2 | 0 |
8 | Cu(CH3CN)4PF6 | CH2CI2 | 27 |
9 | CuCI | CH2CI2 | 35 |
10 | CuBr | CH2CI2 | 43 |
11 | CuI | CH2CI2 | 64 |
12 | - | CH2CI2 | 45 |
13c | CuI | CH2CI2 | 63 |
14d | CuI | CH2CI2 | 68 |
15 | CuI | Toluene | 64 |
16 | CuI | THF | 70 |
17 | CuI | Et2O | 71 |
18e | CuI | Et2O | 76 |
19f | CuI | Et2O | 85 |
20f | - | Et2O | 43 |
21g | CuI | Et2O | >99 (98)h |
Reaction run in 0.5 m solution.
Based on 1H NMR.
Using 6 mol % CuI.
Using 3 mol % Grubbs-2 and 6 mol % CuI.
Reaction run in 0.2 m solution.
Reaction run in 0.1 m solution.
At 35 °C for 3 h; without CuI; yield = 57%
Isolated yield.