Table 1.
| ||||||
---|---|---|---|---|---|---|
no | 1 | cat. | ligand | base | deviation from standard conditions | Yield of 3ab (%) |
1 | 1a | Pd(PPh3)4 | - | Cs2CO3 | toluene, 50 °C | dec. |
2 | 1a | Pd(dppf)Cl2 | - | Cy2NMe | PhCF3, 110 °C | dec. |
3 | 1a | Pd(OAc)2 | Xantphos | Cs2CO3 | - | 87 |
4 | 1a | Pd(PPh3)4 | - | Cs2CO3 | THF | 14 |
5 | 1a | Pd(OAc)2 | DPEPhos | Cs2CO3 | - | 7 |
6 | 1a | Pd(OAc)2 | t-Bu-Xantphos | Cs2CO3 | - | 0 |
7 | 1a | Pd(OAc)2 | L | Cs2CO3 | - | 7 |
8 | 1a | Pd(OAc)2 | Xantphos | Cs2CO3 | no light, 40 °C | traces |
9 | 1a | - | Xantphos | Cs2CO3 | - | 0 |
10 | 1d | Pd(dppf)Cl2 | - | Cy2NMe | PhCF3, 110 °C | dec. |
11 | 1d | Pd(OAc)2 | Xantphos | Cs2CO3 | - | 67 |
12 | 1d | Pd(OAc)2 | Xantphos | Cs2CO3 | no light, rt | 88 |
13 | 1h | Pd(dppf)Cl2 | - | Cy2NMe | PhCF3, 110 °C | dec. |
14 | 1h | Pd(OAc)2 | Xantphos | Cs2CO3 | - | 30 |
15 | 1h | Xantphos Pd G3 | - | iPr2NEt | - | 86 |
16 | 1h | Xantphos Pd G3 | - | iPr2NEt | no light, 40 °C | 96 |
Conditions: 1a 0.1 mmol scale, catalyst (10 mol %), ligand (20 mol %), base (2 equiv), benzene (0.5 M), 34 W blue LED.
GC–MS yield.