Synthesis of 4a–4ya.
| |||
|---|---|---|---|
| Entry | 1, Ar = | 2, Ar′ = | 4b, (%) |
| 1 | 1a, Ph | 2a, Ph | 4a, 81 |
| 2 | 1a, Ph | 2b, 4-MeOC6H4 | 4b, 82 |
| 3 | 1a, Ph | 2c, 3-MeOC6H4 | 4c, 80 |
| 4 | 1a, Ph | 2d, 3,4,5-(MeO)3C6H2 | 4d, 78 |
| 5 | 1a, Ph | 2e, 2,3,4-(MeO)3C6H2 | 4e, 72 |
| 6 | 1a, Ph | 2f, 3,4-CH2O2C6H3 | 4f, 73 |
| 7 | 1a, Ph | 2g, 4-PhC6H4 | 4g, 80 |
| 8 | 1a, Ph | 2h, 3,4-(MeO)2C6H3 | 4h, 72 |
| 9 | 1a, Ph | 2i, 3,4-Cl2C6H3 | 4i, 78 |
| 10 | 1a, Ph | 2a, Ph | 4j, 80 |
| 11 | 1b, 4-MeOC6H4 | 2a, Ph | 4k, 76 |
| 12 | 1c, 3-MeOC6H4 | 2a, Ph | 4l, 68 |
| 13 | 1d, 3-MeO-5-HOC6H3 | 2a, Ph | 4m, 64 |
| 14 | 1e, 3,5-(MeO)2C6H3 | 2j, 4-NO2C6H4 | 4n, 76 |
| 15 | 1a, Ph | 2k, 2-naphthyl | 4o, 70 |
| 16 | 1a, Ph | 2l, 2-FC6H4 | 4p, 67 |
| 17 | 1a, Ph | 2m, 2-furyl | 4q, 60c |
| 18 | 1a, Ph | 2n, 2-thienyl | 4r, 62 |
| 19 | 1a, Ph | 2o, 1-naphthyl | 4s, 75 |
| 20 | 1f, 4-FC6H4 | 2h, 3,4-(MeO)2C6H3 | 4t, 73 |
| 21 | 1g, 4-ClC6H4 | 2h, 3,4-(MeO)2C6H3 | 4u, 72 |
| 22 | 1h, 4-BrC6H4 | 2h, 3,4-(MeO)2C6H3 | 4v, 66 |
| 23 | 1i, 4-MeC6H4 | 2h, 3,4-(MeO)2C6H3 | 4w, 74 |
| 24 | 1c, 3-MeOC6H4 | 2h, 3,4-(MeO)2C6H3 | 4x, 64 |
| 25 | 1j, 3-MeO-2-HOC6H3 | 2a, Ph | 4y, 60 |
| 26 | 1k, 2-NO2C6H4 | 2a, Ph | 4z, —d |
All reactions were run on a 1.0 mmol scale with phenols 1a–1k, cinnamoyl chlorides (2a–2o, 1.0 equiv.), BiCl3 (315 mg, 1.0 equiv.), CCl4 (20 mL), 10 h, reflux (77 °C); then RuCl3·3H2O (261 mg, 1.0 equiv.) was added into the reaction mixture, 5 h, reflux (monitored by TLC).
Isolated yields.
3q (10%) was obtained.
No detection.