Table 3. Copper-Catalyzed Indolation of THIQ.
| entry | R | X | amt of THIQ (equiv) | yield (%) |
|---|---|---|---|---|
| 1 (5h) | H | CH | 8.0 | 84 |
| 2 (5h) | H | CH | 4.0 | 85 |
| 3 (5h) | H | CH | 2.0 | 74 |
| 4 (5h) | H | CH | 0.8 | 48 |
| 5 (5h) | H | CH | 0.4 | 53 |
| 6 (5i) | 1-Me | CH | 0.8 | 1 |
| 7 (5j) | 2-Me | CH | 0.8 | 43 |
| 8 | 3-Me | CH | 0.8 | ncb |
| 9 (5l) | 5-OMe | CH | 0.8 | 48 |
| 10 (5l) | 5-OMe | CH | 2.0 | 71 |
| 11 (5m) | 5-NO2 | CH | 0.8 | 53a |
| 12 (5m) | 5-NO2 | CH | 2.0 | 62a |
| 13 (5n) | 5-COOMe | CH | 2.0 | 58 |
| 14 (5p) | 6-Cl | CH | 0.8 | 46 |
| 15 (5q) | 7-NO2 | CH | 0.8 | 2 |
| 16 (5r) | N | 0.8 | 43 | |
| 17 (5t) | 7-Me | CH | 0.8 | 48 |
| 18 (5t) | 7-Me | CH | 2.0 | 68 |
Reaction time: 2 days.
nc = no conversion.
