Optimisation of the reaction conditions. Reaction conditions: benzylamine (1a, 2.0 mmol), phenylboronic acid (2a, 0.5 mmol), isoamyl nitrite (2.5 mmol), sodium carbonate (0.5 mmol), chloroform (1.25 mL), 60 °C, 24 h.
| ||
|---|---|---|
| Entry | Deviation from standard conditions | Yielda [%] |
| 1 | No deviation | 80 (70)b |
| 2 | No iAmONO | 0 |
| 3 | No base | 72 |
| 4 | Pinacol ester instead of phenylboronic acid | 0 |
| 5 | t BuONO instead of iAmONO | 23 |
| 6 | 1 equiv. of boric acid (B(OH)3) | 70 |
GC yield of the crude reaction mixture using n-dodecane as an internal standard.
Isolated yield.