Screening of reaction conditionsa.
| ||||||
|---|---|---|---|---|---|---|
| Entry | Cat. | [N3] | Oxidant | Solvent | 2a [%] | 3a [%] |
| 1 | — | — | NIS (3.0 equiv.) | EA | 0 | 0 |
| 2 | — | NaN3 (3.0 equiv.) | NIS (3.0 equiv.) | EA | 54 | Trace |
| 3b | — | NaN3 (3.0 equiv.) | NIS (3.0 equiv.) | EA | 15 | 0 |
| 4 | — | NaN3 (3.0 equiv.) | PIDA (1.8 equiv.) | EA | 23 | 0 |
| 5 c | FeCl2 | NaN 3 (3.6 equiv.) | PIDA (1.8 equiv.) | EA | 71 (64) | 0 |
| 6d | — | TMSN3 (2.0 equiv.) | NIS (2.0 equiv.) | DCE | 0 | 40 |
| 7 d | — | TMSN 3 (2.5 equiv.) | NIS (2.5 equiv.) | CCl 4 | 0 | 68 (65) |
a
Reaction conditions: 1a (0.4 mmol) and additives in EA (4.0 mL) under Ar, 80 °C, and 12 h. Determined by 1H NMR analysis using 1,1,2,2-tetrachloroethane as the internal standard. Isolated yield in parentheses.
b
NaI (2.0 equiv.) as the additive.
c
NaI (30 mol%) as the additive.
d
1a (0.2 mmol) and open air reaction.