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. 2018 Sep 10;9(44):8416–8425. doi: 10.1039/c8sc03525c

Table 1. Reaction optimization using anisole a .

Inline graphic
Entry Catalyst b Solvent c Temperature (time) Yield d (%)
3aA 2aA
1 Ph3PAuCl/AgSbF6 DCE 80 °C (44 h) 0 0
2 IPrAuNTf2 DCE 80 °C (24 h) 0 36
3 XPhosAuCl/AgNTf2 DCE 80 °C (21 h) 0 57
4 BrettPhosAu(MeCN)SbF6 DCE 80 °C (30 h) 0 65
5 JohnPhosAu(MeCN)SbF6 DCE 80 °C (26 h) 44 26
6 JohnPhosAu(MeCN)SbF6 Benzene 80 °C (10 h) 0 78
7 JohnPhosAu(MeCN)SbF6 Propan-2-ol 80 °C (10 h) 0 63
8 JohnPhosAu(MeCN)SbF6 1,4-Dioxane 80 °C (10 h) 0 87
9 JohnPhosAu(MeCN)SbF6 TCE 140 °C (13 h) 55 0
10 JohnPhosAu(MeCN)SbF 6 TCE (condition A) 80 °C (1 h), 140 °C (16 h) 75 0
11 BrettPhosAu(MeCN)SbF6 Anisole 80 °C (15 h) 13 28
12 BrettPhosAu(MeCN)SbF 6 Anisole (condition B) 140 °C (19.5 h) 86 0

aReactions were carried out using 1a (1 equiv.), 8A (10 equiv.), and the gold catalyst (5 mol%).

bThe ligand structures are shown in Fig. 2. BrettPhosAu(MeCN)SbF6, JohnPhosAu(MeCN)SbF6, and IPrAuNTf2 were prepared in advance. The other catalysts were prepared in situ by mixing the AuCl ligand with AgNTf2 or AgSbF6.

cDCE = 1,2-dichloroethane, TCE = 1,1,2,2-tetrachloroethane.

dIsolated yields.