Table 4.
entry | ynamides | enaminesa | vinylogous amidines | yield [%]b |
---|---|---|---|---|
1 |
8a: R = Ts 8h: R = MBS |
41 |
45 46 |
52c |
2 | 71d | |||
3 | 8f | 42 | 47 | 58e |
4 | 8d | 41 | 48 | 54f |
5 | 8i | 41 | 49 | 57g |
6 | 8j | 43 | 50 | -- |
7 | 42 | 51 | 62h |
Unless otherwise noted, all reactions utilized 3.0 equiv of the enamine, 5.0 mol% Pd2(dba)3, and 10.0 mol% of xantphos; and were run in THF [conc = 0.05 M].
Isolated yields.
2 h at 70°C.
2 h at 50 °C with 1.5 equiv of K2CO3.
12 h at 70°C with 1.5 equiv of 42; 2.0 mol % Pd2(dba)3; and 4.0 mol% of xantphos.
30 min at 50 °C.
2 h at RT.
2 h at 75 °C with 1.5 equiv of K2CO3 and 1.5 equiv of 44.