Screening of catalysts and co-catalystsa.
| |||||
|---|---|---|---|---|---|
| Entry | Catalyst | Co-catalysts | Yield (%) | ||
| 3a | 4a | 5a | |||
| 1 | Pd/C | w/o | 6 | <1 | 4 |
| 2 | Pd/C | TsOH | 85 | <1 | <1 |
| 3 | Pd/C | PhCOOH | 7 | <1 | 5 |
| 4 | Pd/C | CF3COOH | 13 | <1 | 4 |
| 5 | Pd/C | CH3SO3H | 20 | <1 | <1 |
| 6 | Pd/C | Ti(OiPr)4 | 8 | <1 | 3 |
| 7 | Pd/C | Al(OiPr)3 | 5 | <1 | 6 |
| 8 | Pd/C | ZnCl2 | <1 | <1 | <1 |
| 9 | Pd/C | B(C6F5)3 | 6 | <1 | <1 |
| 10 | Pd/C | Sc(O3SCF3)3 | 1 | <1 | 1 |
| 11 | Pd/C | Na2CO3 | 2 | <1 | 7 |
| 12 | Pd/C | K2CO3 | 1 | <1 | 69 |
| 13 | Pd/TiO2 | TsOH | 54 | <1 | <1 |
| 14 | Pd/Al2O3 | TsOH | 4 | <1 | <1 |
| 15 | Pd/CeO2 | TsOH | 11 | <1 | 1 |
| 16 | Pd/LDH | TsOH | <1 | <1 | 9 |
| 17 | Ru/C | TsOH | 3 | <1 | <1 |
| 18 | Rh/C | TsOH | 54 | 13 | <1 |
| 19 | Pt/C | TsOH | 39 | 31 | <1 |
Reaction conditions: catalyst (metal: 2 mol%), additive (10 mol%), 1a (0.5 mmol), 2a (0.5 mmol), mesitylene (2 mL), Ar (1 atm), temperature 160 °C, and time 2 h. Yields were determined by GC and are relative to 1a.