Table 5. Screening of Conditionsa.
entry | atmosphere | solvent | convb (%) | yieldc,d (%) |
---|---|---|---|---|
1 | argon | pinacolone | 86 | 69 [64] |
2 | argon | acetone/dioxane (1:1) | 82 | 62 |
3 | argon | cyclohexanone | 83 | 61 |
4 | argon | acetophenone | 80 | 61 |
5 | air | pinacolone | 91 | 73 [61] |
6 | CO | pinacolone | 65 | 43 |
7 | H2 | pinacolone | 97 | 93 [91] |
8 | argone | 3-ethyl-3-pentanol | 96 | 45 |
9 | argonf | pinacolone | 99 | 59 [53] |
Reaction conditions: 4a (0.5 mmol), 6a (0.75 mmol), Ru3(CO)12 (5 mol %), and pinacolone (0.5 mL).
Conversion based on GC analysis with respect to 4a (dodecane as internal standard).
Yield determined by GC analysis with respect to 4a (dodecane as internal standard).
Number in brackets is yield of 5a.
The reaction was performed in a vial with septum and argon balloon.
Microwave reaction: 170 °C for 2.5 h.