Table 1. Reaction Conditions Optimizationa.
entry | change from the standard conditions | yield (%)b |
---|---|---|
1 | none | 76 |
2 | NiCl2(PPh3)2 instead of Ni(acac)2 | trace |
3 | Ni(cod)2 instead of Ni(acac)2 | 40 |
4 | NiCl2[P(CH3)3]2 instead of Ni(acac)2 | 28 |
5 | Ni(dppf)Cl2 instead of Ni(acac)2 | trace |
6 | Ni(PPh3)4 instead of Ni(acac)2 | trace |
7 | NiCl2 instead of Ni(acac)2 | trace |
8 | 254 nm UV instead of blue LED | trace |
9 | 365 nm UV instead of blue LED | trace |
10 | filament lamp instead of blue LED | trace |
11 | DMSO instead of DMF | no reaction |
12 | o-xylene instead of DMF | 29 |
13 | THF instead of DMF | 50 |
14 | dioxane instead of DMF | trace |
15 | EtOAc instead of DMF | 16 |
16 | DCE instead of DMF | trace |
17 | air instead of SeO2 | 49 |
18 | CuCl2 instead of SeO2 | |
19 | Cu(OAc)2 instead of SeO2 | 20 |
20 | BQ instead of SeO2 | |
21 | MnO2 instead of SeO2 | |
22 | m-CPBA instead of SeO2 | |
23 | BPO instead of SeO2 | 15 |
24 | t-BuOOH instead of SeO2 | |
25 | AgOAc instead of SeO2 | 30 |
Ynone 1a (0.2 mmol, 1.0 equiv) and catalyst (0.02 mmol, 10 mol %) in solvent (2 mL) under irradiation using light source with oxidant (0.3 mmol, 1.5 equiv) at room temperature for 5 h.
Isolated yield.