Table 2. Three-Component Reaction of Propargylic Alcohol, CO2, and Vicinal Diola.
| 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 |
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.
GC yield.
Isolated yield.
CO2, 1.0 MPa.
CO2, 1.0 bar.
