Table 3.
Effect of base and solvent Suzuki cross coupling of 4′-bromoacetophenone (6a) with phenylboronic acid (5) under thermal conditions.
| Entry | Base | Solvent/co-catalyst | Yield%a |
|---|---|---|---|
| 1 | K2CO3 | H2O/TBAB | 100 (95) |
| 2 | K2CO3 | H2O/TBAI | 100 (90) |
| 3 | K2CO3 | H2O/TBATFB | 100 (92) |
| 4 | K2CO3 | H2O/CDBAB | 100 (90) |
| 5 | K2CO3 | H2O/CTAB | 80 (78) |
| 6 | K2CO3 | DMF | 77 (75) |
| 7 | K2CO3 | Acetonitrile | 84 (83) |
| 8 | K2CO3 | Toluene | 100 (83) |
| 9 | K2CO3 | Dioxane | 100 (95) |
| 10 | K2CO3 | Benzene | 84 (80) |
| 11 | K2CO3 | THF | 88 (87) |
| 12 | TEA | H2O/TBAB | 83 (80) |
| 13 | KOH | H2O/TBAB | 90 (87) |
| 14 | KOH | DMF | 100 (93) |
| 15 | KOH | Toluene | 100 (91) |
| 16 | KOH | THF | 100 (81) |
Conversion by GC-analysis and the value between parenthesis indicates the product isolated yield%. Conditions: 4′-Bromoacetophenone/phenylboronic acid/co-catalyst (if used)/base/solvents: 1/1.2/0.6/1/10 mL, under thermal heating at 100 °C for 3 h.