Table 1.
Entry | Substrate | Product | Equiv. TBHP |
%Yield b |
---|---|---|---|---|
1 | 10.0 8.0 |
84 76 |
||
2 | 10.0 | 76 | ||
3 | 10.0 | 87 | ||
4 | 10.0 8.0 |
85 82 |
||
5 | 8.0 | 65 | ||
6 | 8.0 | 70 | ||
7 | 8.0 | 64 | ||
8 | 8.0 | 32 |
Reactions were performed with 1.36 mmol of substrate in 2.5 mL of DCE to which was added 4.0 or 5.0 equiv of TBHP (70% in water) and 0.50 mol % Rh2(cap)4 and the solution was heated at 40 °C. After 16 hours an additional 4.0 or 5.0 equiv of TBHP (70% in water) and 0.50 mol % Rh2(cap)4 was added, and reaction was continued for an additional 24 hours.
Isolated yield after column chromatography; carboxylic acids were purified by recrystallization from ethyl acetate and the mass yield after recrystallation is given.