Table 5.
Entry | R1 | R2 | Yield (%) 2 |
---|---|---|---|
1 | Ph | H | 74 |
2 | 4-Me-Ph | H | 71 |
3 | 4-n-Pr-Ph | H | 70 |
4 | 4-n-amyl-Ph | H | 68 |
5 | 4-t-Bu-Ph | H | 63 |
6 | 4-Cy-Ph | H | 60 |
7 | 4-SMe-Ph | H | 82 |
8 | 4-OMe-Ph | H | 65 |
9 | 4-OBn-Ph | H | 67 |
10 | 4-Ph-Ph | H | 63 |
11 | 4-F-Ph | H | 45 |
12 | 4-Cl-Ph | H | 40 |
13 | 4-I-Ph | H | 39 |
14 | 3-Me-Ph | H | 65 |
15 | 2-NaPh | H | 58 |
16 | (3-Me,5-Me)-Ph | H | 68 |
17 | (3-OMe,4-OMe)-Ph | H | 56 |
18 | (3-OMe,4-OMe,5-OMe)-Ph | H | 73 |
19 | H | 64 | |
20 | H | 71 | |
21 | H | 69 | |
22 | H | 76 | |
23 | H | 75 |
1 Reaction conditions: ketone (0.2 mmol), 1-3-diaminopropane (0.6 mmol), acidified LSA-FAS-Cu2+ [(40 mol%), −SO3H (0.5 equiv)], O2 (1 atm), EtOH (1 mL), 100 °C, 26 h. Isolated yields. Note: For the sake of clarity, the group R2 is indicated in the reaction scheme, albeit R2 = H for all the examples. 2 Isolated yield.