Table 1.
Reaction conditions used for coupling reactions.
| aryl bromide | 19 | LDA | B(OMe)3 | stirring timea | Pd(PPh3)Cl2 | K2CO3 (1 M) | product | yield | |
| [equiv] | [equiv] | [equiv] | [equiv] | [mol %] | [equiv] | ||||
 8 |
1.2 | 1.0 | 1.1 | 1.5 | 15 h | 8 | 1.65 |
 4 |
84% |
| 1.2 | 1.0 | 1.1 | 1.5 | 15 h | 8 | 1.65 | 87% | ||
| 1.0 | 1.25 | 1.4 | 1.9 | 1.5 h | 8 | 2.0 | 89% | ||
 9 |
1.1 | 1.0 | 1.1 | 1.5 | 1.5 h | 8 | 1.65 |
 2 |
41% |
| 1.1 | 1.0 | 1.1 | 1.5 | 16 h | 8 | 1.65 | 39% | ||
 10 |
1.1 | 1.0 | 1.1 | 1.5 | 0.5 h | 5 | 1.65 |
 6 |
52% |
| 1.0 | 1.3 | 1.25 | 1.3 | 0.5 h | 5 | 1.6 | 85% | ||
| 1.0 | 1.5 | 1.55 | 1.6 | 1.2 h | 5 | 2.0 | 87% | ||
aStirring time: After addition of B(OMe)3 at 0 °C to RT.