Table 1.
Investigation of Pd Precursors for OAC Formationa
| |||||
|---|---|---|---|---|---|
| Entry | Pd Precursor | L | Temp (°C) | Yield A (%) | Yield B (%) |
| 1b | P1 | RuPhos | rt | n/a | 99 |
| 2b | P1 | XPhos | rt | n/a | 97 |
| 3b | P1 | t-BuXPhos | rt | n/a | 99 |
| 4b | P2 | RuPhos | rt | n/a | 98 |
| 5b | P2 | XPhos | rt | n/a | 99 |
| 6b | P2 | t-BuXPhos | rt | n/a | 40 |
| 7 | P3 | RuPhos | rt | 99 | 0 |
| 8 | P3 | XPhos | rt | 70 | 0 |
| 9 | P3 | t-BuXPhos | rt | 0 | 10 |
| 10 | P3 | t-BuBrettPhos | rt | 0 | 0 |
| 11 | P3 | RuPhos | 60 | 41 | 59 |
| 12 | P3 | XPhos | 60 | 0 | 99 |
| 13 | P3 | t-BuXPhos | 60 | 0 | 82 |
| 14 | P3 | t-BuBrettPhos | 60 | 0 | 24 |
| |||||
Yields determined by 1H NMR using 0.5 equiv of 1,3,5-trimethoxybenzene as an internal standard. Reaction conditions: Pd precursor (0.05 mmol), L (0.055 mmol), aryl bromide (0.075 mmol), and THF (0.50 mL, 0.10 M).
Reactions run for 16 h.