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. 2017 Jan 31;2(1):337–345. doi: 10.1021/acsomega.6b00407

Table 2. Three-Component Reaction of Propargylic Alcohol, CO2, and Vicinal Diola.

graphic file with name ao-2016-004079_0007.jpg

entry catalyst ligand/additive 3a yield (%)b 4a yield (%)b
1     0 0
2 Ag2CO3 PPh3 57 59
3 Ag2O PPh3 51 49
4 AgOAc PPh3 47 46
5 Ag2WO4 PPh3 54 48
6 AgNO3 PPh3 0 0
7 AgBF4 PPh3 0 0
8 Ag2CO3   0 0
9 PPh3   0 0
10 Ag2CO3 L1 83 82
11 Ag2CO3 L2 88 92
12 Ag2CO3 L3 75 78
13 Ag2CO3 L4 73 73
14 Ag2CO3 L5 74 76
15 Ag2CO3 L6 93(87)c 91
16 Ag2CO3 L7 82 82
17d Ag2CO3 L6 92 92
18e Ag2CO3 L6 59 57
a

Reaction conditions: 1a, 152.2 mg, 2 mmol; 2a, 168.2 mg, 2 mmol; CO2, 2 MPa; catalyst, 0.1 mmol, 5 mol %; ligand/additive, 0.2 mmol, 10 mol %; CH3CN, 2 mL; 80 °C; 12 h.

b

GC yield.

c

Isolated yield.

d

CO2, 1.0 MPa.

e

CO2, 1.0 bar.