| Entry | Aryl halides | Time | Yield b/% | Yield c/% | Yield d/% | Yield e/% |
|---|---|---|---|---|---|---|
| 1 |  |
15 min | 94.3 | 93.5 | 90.3 | 92.4 |
| 2 |  |
15 min | 98.4 | 97.1 | 96.7 | 96.9 |
| 3 |  |
15 min | 96.3 | 96.0 | 89.4 | 93.5 |
| 4 |  |
15 min | 99.3 | 98.8 | 97.8 | 98.2 |
| 5 |  |
15 min | 92.7 | 90.3 | 87.2 | 88.6 |
| 6 |  |
15 min | 98.6 | 98.2 | 97.5 | 98.1 |
| 7 |  |
15 min | 90.2 | 88.3 | 82.5 | 86.2 |
| 8 |  |
30 min | 48.1 | 42.5 | 37.8 | 40.0 |
| 9f |  |
6 h | 15.9 | 13.6 | 9.5 | 11.2 |
| 10f |  |
6 h | 34.2 | 30.2 | 18.1 | 26.4 |
| 11f |  |
6 h | 45.6 | 38.3 | 29.5 | 37.4 |
| 12f |  |
6 h | 88.9 | 84.8 | 70.6 | 76.3 |
| 13f |  |
6 h | 65.6 | 59.6 | 46.7 | 55.2 |
| 14f |  |
6 h | 47.8 | 37.3 | 22.7 | 35.5 |
a Reaction conditions: aryl halide (1 mmol), phenylboronic acid (6 mmol), K2CO3 (2 mmol), PdNPs (0.1 mmol‰), EtOH/H2O (6 ml/6 ml).
b PdNPs-EG
c PdNPs-KBr-EG
d PdNPs-CA
e PdNPs-KBr-CA
f PdNPs (1mmol‰).