Table 2.
Entry | PdI2 (mol%) | 1 | 2 | 3 | Yield of 3 (%) b |
---|---|---|---|---|---|
1 | 1 | 72 | |||
2 | 0.33 | 1a | 2a | 3aa | 55 |
3 | 1 | 1a | 67 | ||
4 | 0.33 | 1a | 2b | 3ab | 55 |
5 | 1 | 1a | 75 | ||
6 | 0.33 | 1a | 2c | 3ac | 58 |
7 | 1 | 1a | 74 | ||
8 | 0.33 | 1a | 2d | 3ad | 59 |
9 | 1 | 1a | 54 | ||
10 | 1 | 1a | 74 | ||
11 | 0.33 | 1a | 2f | 3af | 61 |
12 | 1 | 2a | 81 | ||
13 | 0.33 | 1b | 2a | 3ba | 68 |
14 | 1 | 2a | 67 | ||
15 | 0.33 | 1c | 2a | 3ca | 58 |
16 | 1 | 2f | 66 | ||
17 | 1 | 2a | 68 | ||
18 | 0.33 | 1e | 2a | 3ea | 62 |
19 | 1 | 2a | 54 | ||
20 | 1 | 2f | 48 | ||
25 | |||||
21 | 1 | 2a | 70 | ||
22 | 0.33 | 1h | 2a | 3ha | 58 |
23 | 1 | 2a | 69 | ||
24 | 0.33 | 1i | 2a | 3ia | 58 |
25 | 1 | 2a | 68 | ||
26 | 0.33 | 1j | 2a | 3ja | 63 |
27 | 1 | 2a | 71 | ||
28 | 0.33 | 1k | 2a | 3ka | 60 |
29 | 1 | 2a | 67 | ||
30 | 0.33 | 1l | 2a | 3la | 56 |
31 | 1 | 2a | 57 | ||
32 | 1 | 2c | 72 | ||
33 | 0.33 | 1n | 2c | 3nc | 67 |
a All reactions were carried out in MeCN as the solvent (0.20 mmol of 1 per mL of MeCN), in the presence of PdI2 (1 mol% or 0.33 mol%), KI (KI:PdI2 molar ratio = 100), and amine 2 (4 equiv) for 15 h, under 20 atm of a 4:1 mixture of CO–air. Substrate conversion was quantitative in all cases. b Isolated yield based on starting 1.