Table 1.
Entrya | Catalyst | Additive (equiv) | Conversion (%)b |
Yield (%)c |
---|---|---|---|---|
1 | none | KF (3.0) | <5 | <5 |
2 | CuI | KF (3.0) | <5 | <5 |
3 | CuBr2 | KF (3.0) | <5 | <5 |
4 | CuOAc | KF (3.0) | >95 | 72 |
5 | Cu(OAc)2 | KF (3.0) | >95 | 75 |
6 | Cu(TFA)2 | KF (3.0) | 78 | 56 |
7 | Cu(OTf)2 | KF (3.0) | <5 | <5 |
8 | Cu(SO4)2 | KF (3.0) | <5 | <5 |
9 | Cu(OAc)2 | none | 100 | 58 |
10 | Cu(OAc)2 | KOAc (1.0) | 100 | 78 |
11 | Cu(OAc)2 | KOAc (0.5) AcOH (0.5) |
100 | 80 |
Reactions were carried out under O2 at 40 °C, unless stated otherwise.
Conversions were determined by 1H NMR analysis with 1,3,5-trimethoxybenzene as an internal standard.
Isolated yield.