Table 6.
Chemoselective Suzuki-Miyaura cross-coupling of 2-B(pin)-substituted allylic acetates with aryl bromides.
| |||||
|---|---|---|---|---|---|
| Entry | Acetate | Ar-Br | Product | Yield (%)[a] | |
| 1 | 1a | Ph-Br |
|
6a | 73 |
| 2 | 1a | 4-MeO-C6H4-Br |
|
6b | 54 |
| 3 | 1a | 4-O2N-C6H4-Br |
|
6c | 91 |
| 4 | 1a | 4-F3C-C6H4-Br |
|
6j | 85 |
| 5 | 1a | 2-MeO-C6H4-Br |
|
6k | 80 |
| 6 | 1b | Ph-Br |
|
6d | 87 |
| 7 | 1d | 4-O2N-C6H4-Br |
|
6f | 90 |
| 8 | 1f | 4-O2N-C6H4-Br |
|
6h | 80[b] |
| 9 | 1a |
|
|
6l | 74 |
| 10 | 1a |
|
|
6m | 82 |
Yield of isolated and purified products.
The reaction was conducted at 75 °C in THF/H2O (10:1).