Table 2.
Aerobic Allylic Acetoxylation of Terminal Olefins.a
 | |||||
|---|---|---|---|---|---|
| Entry | Substrate | Time (h) | Product | E:Zb | Yieldc |
| 1 |  |
24 |  |
17:1 | 81% (89%) |
| 2 |  |
24 |  |
14:1 | 79% (87%) |
| 3 |  |
24 |  |
6:1 | 68% (68%) |
| 4 |  |
48 |  |
10:1 | 76% (82%)d |
| 5 |  |
24 |  |
19:1 | 70% (76%) |
| 6 |  |
24 |  |
21:1 | 84% (92%) |
| 7 |  |
48 |  |
6:1 | 52% (72%) |
| 8 |  |
48 |  |
29:1 | 76% (87%) |
| 9 |  |
24 |  |
7:1 | 76% (84%)e |
| 10 |  |
48 |  |
36:1 | 71% (84%) |
| 11 |  |
24 |  |
16:1 | 74% (86%) |
a
Reaction conditions: 5 mol % Pd(OAc)2 (0.05 mmol), 5 mol % 1 (0.05 mmol), 20 mol % NaOAc (0.20 mmol), substrate (1.0 mmol), dioxane (2.8 mL), AcOH (0.9 mL, 16 mmol), 1 atm O2, 60 °C.
b
Based on GC analysis of the crude mixture.
c
Isolated yields. GC yields are given in parenthesis.
d
3:1 mixture of allylic and homoallylic acetates.
e
4 atm O2. 5:1 mixture of linear and branched isomers.