Table 2.
entry | primary amines | 4-pentenyl-amidines | yield [%]b | |
---|---|---|---|---|
1 | 9 | ≥95 | ||
2 | 10 | 90 | ||
3 | 11 | 73 | ||
4 | 12 | 76 | ||
5 | 13 | 67 | ||
6 | 14 | 85c | ||
7 | 15 | 78d | ||
8 | 16 | 54 | ||
9 | 17 | 52 |
All reactions utilized ynamide 6, 5.0 mol % Pd(PPh3)4, 1.0 equiv K2CO3, 3.0 equiv RNH2, THF [conc = 0.05 M], 65 °C, 5–8 h.
Isolated yields.
1.0 equiv of amine was used.
Reaction time was 24 h.