Table 1. Screening of Oxidants for the Synthesis of 3-Indolylquinone.
| entry | oxidant | catalyst | yieldab, % |
|---|---|---|---|
| 1 | air | NR | |
| 2 | oxygen | NR | |
| 3 | H2O2 | NR | |
| 4 | H2O2 | MoO3 | 10a |
| 5 | H2O2 | WO3 | 15a |
| 6 | H2O2 | Fe3O4/PVP–PWA | 10a |
| 7 | Ag2O | 30a/40b | |
| 8 | air | Ag2O | 25a/45b |
| 9 | oxygen | Ag2O | 27a/41b |
| 10 | H2O2 | Ag2O | 94a |
| 11 | H2O2 | AgNO3 | 35a |
| 12 | DDQ | 41a/55b | |
| 13 | KBrO3 | 10a/30b | |
| 14 | K4FeCN6 | NR | |
| 15 | oxone | NR |
Reactions were performed with 1:1 2-methylhydroquinone/2-methylindole, 0.1 g Fe3O4/PVP–PWA (141), 3 mmol oxidant, 10 mL of THF, and 20 mol % catalyst in 1 atm air/oxygen at RT for 2 h. NR, no reaction; isolated yield of 3-indolylquinone after column chromatography. Bold values represent maximum product yield under optimized reaction conditions.
The product 3-indolylhydroquinone is formed.
