Table 1. Preparation of Biphenyl under Different Conditionsa.
entry | solvent | FLA-Pd (g) | base | T (°C) | time (min) | yield (%)b |
---|---|---|---|---|---|---|
1 | THF | 0.05 | K2CO3 | reflux | 120 | 65 |
2 | toluene | 0.05 | K2CO3 | reflux | 120 | 42 |
3 | H2O | 0.05 | – | rt | 240 | 0 |
4 | H2O | 0.05 | – | reflux | 240 | 0 |
5 | EtOH | 0.05 | K2CO3 | reflux | 60 | 70 |
6 | H2O | 0.05 | K2CO3 | reflux | 60 | 93 |
7 | H2O | 0.05 | NaOAc | reflux | 120 | 50 |
8 | H2O | 0.05 | NaHCO3 | reflux | 120 | 76 |
9 | H2O | 0.05 | Et3N | reflux | 120 | 61 |
10 | H2O | 0.05 | n-Pr3N | reflux | 120 | 62 |
11 | H2O | 0.03 | K2CO3 | reflux | 120 | 70 |
12 | H2O | 0.07 | K2CO3 | reflux | 60 | 93 |
Reaction conditions: PhI (1.0 mmol); PhB(OH)2 (1.1 mmol); base (2.0 mmol); solvent (10.0 mL).
Isolated yield of the pure product.