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. 2023 Dec 21;4(2):241–247. doi: 10.1021/acsorginorgau.3c00060

Table 1. Reaction Conditions Optimizationa.

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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
a

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.

b

Isolated yield.