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. 2019 Oct 2;9(53):31162–31168. doi: 10.1039/c9ra03921j

Optimization of the reaction conditions.

graphic file with name c9ra03921j-u1.jpg
Entrya Oxidant Additive Base Solvent Yieldb (%)
1 Cu(OAc)2 — Cs2CO3 DMF 41
2 Cu(OAc)2 — Cs2CO3 DMF 21
3 Cu(OAc)2 — — DMF Trace
4 Cu(OAc)2 AgSbF6 Cs2CO3 DMF 69
5 Cu(OAc)2 AgSbF6 Cs2CO3 DCE 32
6 Cu(OAc)2 AgSbF6 Cs2CO3 Dioxane 39
7 Cu2O AgSbF6 Cs2CO3 DMF Trace
8 CuO AgSbF6 Cs2CO3 DMF Trace
9 CuI AgSbF6 Cs2CO3 DMF Trace
10 Cu(OAc)2 AgSbF6 Cs2CO3 Toluene 13
11 Ag2CO3 — — DMF 31
12 Ag2CO3 AgSbF6 Cs2CO3 DMF 63
13 AgOAc AgSbF6 Cs2CO3 DMF 56
14 AgF AgSbF6 Cs2CO3 DMF 48
15 Cu(OAc)2 AgSbF6 Cs2CO3 DMF 49
16 Cu(OAc)2 AgSbF6 Cs2CO3 DMF 66
17 Cu(OAc)2 AgSbF6 Cs2CO3 DMF 29
a

Reaction conditions: benzaldehyde (1a) (0.5 mmol), alkyne (2a) (0.6 mmol), Pd(OAc)2 (0.011 g, 0.05 mmol), oxidant (1 equiv.), additive (20 mol%), base(1 equiv.), solvent (2 mL).

b

Isolated yield after column chromatography.