Table 1.
Entry | Variation from “standard conditions” | Yield (%)b | |
---|---|---|---|
2a | 3a | ||
1 | none | 78 | <5 |
2 | No LiClO4 | 23 | 10 |
3 | 0.2 mol/L nBu4NOAc instead | 36 | 16 |
4 | 0.5 mol/L LiClO4 instead | trace | <5 |
5 | 0.5 mol/L LiOAc 2H2O as only electrolyte | 36 | <5 |
6 | 5 mL MeOH, no MeCN | 15 | 10 |
7 | MeOH:MeCN = 1:4 | 23 | 8 |
8 | Under Ar | trace | 0 |
9 | Under O2 | 68 | 8 |
10 | “water-free” operation | 38 | <5 |
11 | No [Au] | 0 | <5 |
Conditions: 1a (0.5 mmol), Ph3PAuCl (0.025 mmol), nBu4NOAc (2.5 mmol), LiClO4 (1 mmol), MeOH (4 mL), MeCN (1 mL), air, r.t., 12 h.
1H NMR yields using 1,3,5-trimethoxybenzene as an internal standard.