Table 1.
Optimization of the reaction conditionsa.
| Entry | Variation from standard conditions | Yieldb (%) |
|---|---|---|
| 1 | No deviation | >96 (96c) |
| 2 | Pd(PPh3)2Cl2 instead of Pd(PPh3)4 | 4 |
| 3 | Pd(PPh3)2Cl2/XantPhos (1:2) instead of Pd(PPh3)4 | 7 |
| 4 | Pd(PPh3)2Cl2/PPh3 (1:2) instead of Pd(PPh3)4 | >96 |
| 5 | with the addition of Xantphos or DPEPhos (10 mol %) as ligand | 0, 8 |
| 6 | t-BuBr instead of 2a | 93d |
| 7 | CyI instead of 2a | 87d,e |
| 8 | At 100 oC, in the absence of light irradiation | 0 |
| 9 | Without Pd(PPh3)4 or K2CO3 or light irradiation | 0 |
aReaction conditions: 1a (0.1 mmol), 2a (0.15 mmol), Pd(PPh3)4 (5 mol %), K2CO3 (0.2 mmol), and DMA [0.1 M] under 40 W blue LED irradiation with fan cooling (30 ± 5 °C).
bGC yields using dodecane as an internal standard, unless otherwise noted.
cIsolated yield. E:Z > 20:1.
dNMR yields using 1,1,2,2-tetrachloroethane as an internal standard. E:Z > 20:1.
eYield of the cyclohexyl-substituted product.