Table 2.
Catalysis yields (%)b | ||||||||
---|---|---|---|---|---|---|---|---|
Entry | Propargyl alcohol | R1 | R2 | mmol H2 | Semi-hydrogenation | Full-hydrogenation | Tandem reaction | TOFc |
1 | 2-propyn-1-ol | H | H | 10 | 0 | 42 | 58 | 290 |
2 | 2-propyn-1-ol | H | H | 2 | 0 | 30 | 70 | 350 |
3 | 3-butyn-2-ol | CH3 | H | 2 | 0 | 20 | 76 | 380 |
4 | 2-butyn-1-ol | H | CH3 | 2 | 43 | 13 | 41 | 205 |
5 | 3-phenyl-2-propyn-1-ol | H | Ph | 2 | 24 | 1 | 39 | 195 |
Reaction condition: 50 µL of propargyl alcohol; 5 mol% Pd, 2 mL CDCl3; 4 h.
Yields were determined by 1H NMR.
Initial TOFs are based on the mole isomerized per mole Pd atoms per hour.