Table 2.
entrya | gold catalyst/silver salt | solvent | trans/cisb | yield (%)b |
1 | (t-Bu)2(o-biphenyl)PAuCl/AgOTf | toluene | 5.3:1 | 67 |
2 | (t-Bu)2(o-biphenyl)PAuCl/AgSbF6 | toluene | 2.2:1 | 35 |
3 | (t-Bu)2(o-biphenyl)PAuCl/AgPF6 | toluene | 2.6:1 | 62 |
4 | (t-Bu)2(o-biphenyl)PAuCl /AgBF4 | toluene | – | <5 |
5 | (t-Bu)2(o-biphenyl)PAuCl/AgClO4 | toluene | 4.1:1 | 76 |
6 | Ph3PAuCl/AgClO4 | toluene | – | <5 |
7 | Cy3PAuCl/AgClO4 | toluene | – | <5 |
8 | IPrAuCl/AgClO4c | toluene | 4.4:1 | 63 |
9 | L1AuCl/AgClO4d | toluene | 3.1:1 | 50 |
10 | (t-Bu)2(o-biphenyl)PAuCl/AgClO4 | dioxane | 4.0:1 | 63 |
11 | (t-Bu)2(o-biphenyl)PAuCl/AgClO4 | CH3NO2 | 2.8:1 | 47 |
12e | (t-Bu)2(o-biphenyl)PAuCl/AgClO4 | DCE | 1.8:1 | 34 |
13e | (t-Bu)2(o-biphenyl)PAuCl/AgClO4 | THF | 1.8:1 | 76 |
14e | (t-Bu)2(o-biphenyl)PAuCl/AgClO4 | benzene | 3.2:1 | 60 |
15e | (t-Bu)2(o-biphenyl)PAuCl/AgClO4 | CH3CN | – | <5 |
aReactions were carried out in toluene (0.5 mL) at 0.25 mmol scale, 1a (0.25 mmol) and 2a (0.375 mmol) were added in one portion. bYield and selectivity were determined by 1H NMR spectroscopy (internal standard: trimethyl(phenyl)silane). cIPr= N,N’-bis(2,6-diisopropylphenyl)imidazol-2-ylidene. dL1 = (Cy)2(2',4',6'-triisopropyl-o-biphenyl)P. eReactions were carried out under reflux.