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. 2023 Sep 22;28(19):6764. doi: 10.3390/molecules28196764

Table 2.

Synthesis of 2-(4-acylfuran-2-yl)acetamides 3 by PdI2/KI-catalyzed oxidative aminocarbonylation of 2-propargyl-1,3-dicarbonyl compounds 1 with secondary amines 2 a.

graphic file with name molecules-28-06764-i002.jpg
Entry PdI2 (mol%) 1 2 3 Yield of 3 (%) b
1 1 graphic file with name molecules-28-06764-i003.jpg graphic file with name molecules-28-06764-i004.jpg graphic file with name molecules-28-06764-i005.jpg 72
2 0.33 1a 2a 3aa 55
3 1 1a graphic file with name molecules-28-06764-i006.jpg graphic file with name molecules-28-06764-i007.jpg 67
4 0.33 1a 2b 3ab 55
5 1 1a graphic file with name molecules-28-06764-i008.jpg graphic file with name molecules-28-06764-i009.jpg 75
6 0.33 1a 2c 3ac 58
7 1 1a graphic file with name molecules-28-06764-i010.jpg graphic file with name molecules-28-06764-i011.jpg 74
8 0.33 1a 2d 3ad 59
9 1 1a graphic file with name molecules-28-06764-i012.jpg graphic file with name molecules-28-06764-i013.jpg 54
10 1 1a graphic file with name molecules-28-06764-i014.jpg graphic file with name molecules-28-06764-i015.jpg 74
11 0.33 1a 2f 3af 61
12 1 graphic file with name molecules-28-06764-i016.jpg 2a graphic file with name molecules-28-06764-i017.jpg 81
13 0.33 1b 2a 3ba 68
14 1 graphic file with name molecules-28-06764-i018.jpg 2a graphic file with name molecules-28-06764-i019.jpg 67
15 0.33 1c 2a 3ca 58
16 1 graphic file with name molecules-28-06764-i020.jpg 2f graphic file with name molecules-28-06764-i021.jpg 66
17 1 graphic file with name molecules-28-06764-i022.jpg 2a graphic file with name molecules-28-06764-i023.jpg 68
18 0.33 1e 2a 3ea 62
19 1 graphic file with name molecules-28-06764-i024.jpg 2a graphic file with name molecules-28-06764-i025.jpg 54
20 1 graphic file with name molecules-28-06764-i026.jpg 2f graphic file with name molecules-28-06764-i027.jpg 48
graphic file with name molecules-28-06764-i028.jpg 25
21 1 graphic file with name molecules-28-06764-i029.jpg 2a graphic file with name molecules-28-06764-i030.jpg 70
22 0.33 1h 2a 3ha 58
23 1 graphic file with name molecules-28-06764-i031.jpg 2a graphic file with name molecules-28-06764-i032.jpg 69
24 0.33 1i 2a 3ia 58
25 1 graphic file with name molecules-28-06764-i033.jpg 2a graphic file with name molecules-28-06764-i034.jpg 68
26 0.33 1j 2a 3ja 63
27 1 graphic file with name molecules-28-06764-i035.jpg 2a graphic file with name molecules-28-06764-i036.jpg 71
28 0.33 1k 2a 3ka 60
29 1 graphic file with name molecules-28-06764-i037.jpg 2a graphic file with name molecules-28-06764-i038.jpg 67
30 0.33 1l 2a 3la 56
31 1 graphic file with name molecules-28-06764-i039.jpg 2a graphic file with name molecules-28-06764-i040.jpg 57
32 1 graphic file with name molecules-28-06764-i041.jpg 2c graphic file with name molecules-28-06764-i042.jpg 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.