Table 1.
entry | catalyst | 2 / 3 / 4b | 2, Z / Ec |
---|---|---|---|
1 | Pd(PPh3)4 | 39/31/30 | 98/2 |
2 | PdCl2(PPh3)2 | 53/32/15 | 98/2 |
3 | PdCl2 + 3P(2-Fur)3 | 80/3/17 | 98/2 |
4 | PdCl2 + 3P(2-Tol)3 | 96/2/2 | 99/1 |
5 | PdCl2(Amphos)2d | 88/<1/12 | 68/32 |
6 | Pd[P(t-Bu)3]2 | 38/26/36 | 73/27 |
7 | PdCl2(PCy3)2 | 95/4/1 | 33/67 |
8 | PEPPSI | 55/33/12 | 45/55 |
9 | PdCl2(PCy3)2 + 3PPh3 | 73/9/18 | 98/2 |
10 | PdCl2(PPh3)2 + TMEDAe | 99/<1/<1 | >99/1 |
11 | PdCl2(PPh3)2 + Et3Nf | 79/5/16 | 98/2 |
Conditions: alkylzinc iodide (1.1 mmol, 1.0 M in THF), vinyl iodide (1 mmol), Pd catalyst (2 mol %). Reactions were run at 0.33 M at rt, 4 h (24 h for entries 10 and 11).
by GC.
Z/E-ratio determined by NMR or GC on crude material.
Defined as dichloro-bis(p-dimethylaminophenyl-di-tert-butylphosphine) palladium(II).
1.1 equiv.
2.2 equiv.