Table 1.
Catalyst optimization.[a]
| ||||||
|---|---|---|---|---|---|---|
| Entry | Ligand | 3a/4a[b] | 3a/5a[b] | Isolated yield[c] | ||
| 1 | dppb | 20:1 | 3:1 | 60 | ||
| 2 | dppe[d] | 15:1 | 5:1 | |||
| 3 | PCy3[d] | 13:1 | 4:1 | |||
| 4 | P(2-furyl)3 | 21:1 | 19:1 | 81 | ||
[a]
Conditions: amine 1 (1.0 equiv), vinyl bromide 2a (1.1 equiv), NaOt-Bu (1.2 equiv), Pd2(dba)3 (1 mol%), Ligand (2 mol% of bidentate ligand or 4 mol% of monodentate ligand), toluene (0.25 M), 60 °C.
[b]
Ratios determined by GC analysis of crude reaction mixtures.
[c]
Isolated yields refer to the total yield of an inseparable mixture of products 3a, 4a, and 5a.
[d]
This reaction was conducted at 110 °C.