Table 1. Optimization of reaction conditions.
| |||||
Entry a | Catalyst | Oxidant | Solv. b | T [°C] | Result c |
1 | Pd(OAc)2 | None | ACN | 25 | N.R. |
2 | None | AgOAc | ACN | 25 | N.R. |
3 | Pd(OAc) 2 | AgOAc | ACN | 25 | 86% |
4 | Pd(OAc)2 | AgOAc | ACN | 60 | 83% |
5 | Pd(OAc)2 | AgOAc | THF | 25 | 32% |
6 | Pd(OAc)2 | AgOAc | DCE | 25 | 10% |
7 | Pd(OAc)2 | AgOAc | DMA | 25 | 72% |
8 | Pd(OAc)2 | Cu(OAc)2 | ACN | 25 | 0 |
9 | Pd(OAc)2 | BQ | ACN | 25 | 30% |
a 1a (0.15 mmol), Pd(OAc)2 (0.015 mmol), oxidant (1.5 mmol), in 4 mL of solvent.
bACN = acetonitrile, DMA = dimethylacetamide, DCE = 1,2-dichloroethane, THF = tetrahydrofuran.
cIsolated yields after purification by silica gel chromatography.