Screening of catalysts and reaction conditions for amination of allylic alcoholsa.
| Entry | Catalyst | Au amount (mol%) | Solvent | Time (h) | Yieldb (%) |
|---|---|---|---|---|---|
| 1 | Ph3PAuCl | 0.5 | Dioxane | 1.5 | 67 (85)c |
| 2 | 3a | 0.1 | Dioxane | 1.5 | 89 |
| 3 | 3b | 0.1 | Dioxane | 4 | 90 |
| 4 | 3c | 0.1 | Dioxane | 4 | 90 |
| 5 | 3d | 0.1 | Dioxane | 1.5 | 95 |
| 6 | 3a | 0.05 | Dioxane | 7 | 43 |
| 7 | 3b | 0.05 | Dioxane | 20 | 38 |
| 8 | 3c | 0.05 | Dioxane | 20 | 41 |
| 9 | 3d | 0.05 | Dioxane | 1.5 | 91 |
| 10 | 3d | 0.01 | Dioxane | 8 | 50 |
| 11 | 3d | 0.05 | MeCN | 1.5 | 50 |
| 12 | 3d | 0.05 | MeNO2 | 3 | 75 |
| 13 | 3d | 0.05 | THF | 3 | Trace |
| 14 | 3d | 0.05 | DMF | 3 | n.r. |
| 15 | 3d | 0.05 | DMSO | 3 | n.r. |
| 16 | SBA-PPh2AuCl | 0.5 | Dioxane | 1.5 | 73 |
| 17 | PS-PPh2AuCl | 0.5 | Dioxane | 1.5 | 78 |
| 18 | AgOTf | 0.1 | Dioxane | 1.5 | n.r (29)c |
| 19 | 2d | 0.1 | Dioxane | 24 | n.r |
Reaction conditions: 1 mmol trans-1,3-diphenyl-2-propen-1-ol, 2 mmol p-toluene sulfonamide, 1 : 1 cat. (mol% Au)/AgOTf, 2 mL solvent, argon atmosphere.
Isolated yield.
Data in parentheses were yields avoiding light.