Table 3. Competitive Experiments for the Ru(0)-Catalyzed Reactiona.
entry | reactant 4 | R | X | Y | product 5 | convb (%) | yield (%) |
---|---|---|---|---|---|---|---|
1 | 4e | Me | OiPr | H | 5af | 35 | 25 |
2 | 4f | Me | OMe | H | 5k | 58 | 32 |
3 | 4g | Me | Me | H | 5i | 99 | 76 |
4 | 4a | Me | H | H | 5a | 86 | 64 |
5 | 4h | Me | F | H | 5l | 73 | 44 |
6 | 4i | Me | CF3 | H | 5n | 24 | 15 |
7 | 4j | Mec | CO2Me | H | 5ag | 43 | 26 |
8 | 4g | Me | Me | Cl | 5ah | 69 | 50 |
9 | 4g | Me | Me | CF3 | 5ai | 48 | 33 |
10 | 4k | CF3 | Me | H | 5t | 95 | 80 |
11 | 4m | Phc | Me | H | 5x | 98 | 90 |
12 | 4m | Phc | Me | Me | 5aj | 88 | 73 |
13 | 4m | Phc | Me | t-Bu | 5ak | 76 | 67 |
14 | 4m | Phc | Me | F | 5al | 71 | 60 |
15 | 4m | Phc | Me | CF3 | 5am | 47 | 33 |
Reaction conditions: 4 (0.5 mmol), 6 (0.75 mmol), Ru3(CO)12 (5 mol %), and pinacolone (0.5 mL).
Conversion based on GC analysis with respect to 4 (dodecane as internal standard).
150 °C.