Table 1.
| ||||
---|---|---|---|---|
entry | ArX | amide | product | yieldb |
1 | R = t-Bu | 1 R = t-Bu | 79% | |
2 | R = Me | 2 R = Me | 85% | |
3 | R = CO2Me | 3 R = CO2Me | 87% | |
4 | 79% | |||
5 | 85% | |||
6c | 82% | |||
7 | 76% | |||
8 | 77% | |||
9 | 72% | |||
10 | 70% | |||
11d | 78% |
Reaction conditions: ArONf/ArOTf (1 equiv), amide (2.5 equiv), [(allyl)PdCl]2 (1 mol%), JackiePhos (5 mol%), K2CO3 (2.0 equiv), 3 Å mol sieves (200 mg/mmol), toluene (0.25 M), 110 °C, 17 h.
Yields reported are an average of at least two runs determined to be >95% pure by elemental analysis or 1H NMR.
Pd(OAc)2 (3 mol%), JackiePhos (7 mol%), H2O activation
K3PO4 was used instead of K2CO3.