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. 2011 Aug 11;7:1100–1107. doi: 10.3762/bjoc.7.126

Table 2.

Screening catalysts and solvents.

graphic file with name Beilstein_J_Org_Chem-07-1100-i002.jpg

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.