Table 6.
The catalytic activities of NNN Pd pincer complexes in Suzuki-Miyaura C–C coupling reactiona.
 | ||||||
|---|---|---|---|---|---|---|
| Entry | Catalyst | Substrate | Time (h) | Conversion (%)b | Yield (%)b | TONc |
| 1 | Complex 1 | 4-Bromotoluene | 4 | >91 | >91 | >910 |
| 2 | Complex 2 | 4-Bromotoluene | 4 | >93 | >93 | >930 |
| 3 | Complex 4 | 4-Bromotoluene | 1 | >99 | >99 | >990 |
| 4 | Complex 5 | 4-Bromotoluene | 1 | >98 | >98 | >980 |
| 5 | Complex 4 | 1-Bromo-4-izobutylbenzene | 1 | >98 | >98 | >980 |
| 6 | Complex 5 | 1-Bromo-4-izobutylbenzene | 1 | >94 | >94 | >940 |
| 7 | Complex 5 | 1-Bromo-4-izobutylbenzene | 2 | >96 | >96 | >960 |
| 8 | Complex 4 | 2-Bromo-6-methoxynaphthalene | 1 | 100 | >99 | 1000 |
| 9 | Complex 5 | 2-Bromo-6-methoxynaphthalene | 1 | 100 | >99 | 1000 |
a
Reaction circumstances: Ar–Br (1.0 mmol), phenylboronic acid (1.2 mmol), K2CO3 (1.2 mmol), catalysis (0.001 mmol), EtOH (2 mL) at 110 °C.
b
Yield and conversion rates were determined by GC analysis based on aryl halides in the presence of dodecane used as internal standard.
c
Mole product/mole catalyst.