Cyanosilylation of 4-nitrobenzaldehyde with TMSCNa.
| Entry | Catalyst | Reaction time, h | Catalyst loading, mol% | Solvent | Product yieldb (%) |
|---|---|---|---|---|---|
| 1 | 1 | 1 | 3.0 | CH2Cl2 | 37 |
| 2 | 1 | 2 | 3.0 | CH2Cl2 | 68 |
| 3 | 1 | 4 | 3.0 | CH2Cl2 | 80 |
| 4 | 1 | 6 | 3.0 | CH2Cl2 | 89 |
| 5 | 1 | 8 | 3.0 | CH2Cl2 | 96 |
| 6 | 1 | 10 | 3.0 | CH2Cl2 | >99 |
| 7 | 1 | 10 | 2.0 | CH2Cl2 | 95 |
| 8 | 1 | 10 | 3.0 | CH3CN | 88 |
| 9 | 1 | 10 | 3.0 | THF | 85 |
| 10 | 1 | 10 | 3.0 | CH3OH | 97 |
| 11 | 1 | 10 | 3.0 | CHCl3 | 95 |
| 12 | 2 | 10 | 3.0 | CH2Cl2 | 86 |
| 13 | 3 | 10 | 3.0 | CH2Cl2 | 90 |
| 14 | 4 | 10 | 3.0 | CH2Cl2 | 81 |
| 15 | 5 | 10 | 3.0 | CH2Cl2 | 84 |
| 16 | 6 | 10 | 3.0 | CH2Cl2 | 80 |
| 17 | Blank | 10 | — | CH2Cl2 | 5 |
| 18 | CuCl2·2H2O | 10 | 3.0 | CH2Cl2 | 9 |
| 19 | H2mia | 10 | 3.0 | CH2Cl2 | 6 |
a
Conditions: 4-nitrobenzaldehyde (0.5 mmol), TMSCN (1.0 mmol), catalyst (2–3 mol%), solvent (2.5 mL), 35 °C.
b
Yield based on 1H NMR analysis: [moles of product per mol of aldehyde substrate] × 100%.