Table 1.
Optimization conditions for forming 3a
| Entry | [Au] (1 mol%) | Solvent | Yield (%)b |
|---|---|---|---|
| 1 | JohnPhosAu(MeCN)SbF6 | DCE | 65 |
| 2 | Ph3PAuCl | DCE | 56 |
| 3 | XPhosAuCl | DCE | 48 |
| 4 | SPhosAuCl | DCE | trace |
| 5 | IPrAuNTf2 | DCE | 29 |
| 6 | AuCl3 | DCE | 25 |
| 7 | AuCl | DCE | 15 |
| 8 | JohnPhosAu(MeCN)SbF6 | THF | N.R. |
| 9 | JohnPhosAu(MeCN)SbF6 | Acetone | N.R. |
| 10 | JohnPhosAu(MeCN)SbF6 | DCM | 50 |
| 11 | JohnPhosAu(MeCN)SbF6 | Toluene | 25 |
| 12c | JohnPhosAu(MeCN)SbF6 | DCE | 54 |
| 13d | JohnPhosAu(MeCN)SbF6 | DCE | 49 |
aReaction conditions: 1a (0.2 mmol), 2a (0.4 mmol), and at room temperature in the solvent (2.0 ml) for 6 h.
bIsolated yield based on 1a.
cThe reaction was conducted at 40 °C for 6 h.
dThe reaction was conducted at 55 °C for 6 h.
N.R. = not reaction. JohnPhos = 2-(di-tert-butylphosphino)biphenyl, SPhos = 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl, XPhos = 2-(dicyclohexylphosphino)-2’,4’,6’-tri-i-propyl-1,1’-biphenyl, IPr = isopropyl, NTf2 = bis(trifluoromethylsulfonyl)imide.