Table 1. Coupling reactions of n-OctX, p-FC6H4MgBr, and 1,3-butadiene a .
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| Entry | Catalyst (mol%) | X | T (°C) | 3aa (%) b | 4aa (%) b |
| 1 | NiBr2(dme) (20) | F | 40 | 50 | 33 |
| 2 | NiBr2(dme) (10) | F | 40 | 48 | 36 |
| 3 | NiBr2(dme) (10) | F | 50 | 49 | 49 |
| 4 | NiBr2(dme) (10) | F | 30 | 63 (48) | 37 (37) |
| 5 | NiBr2(dme) (10) | F | 0 | 31 | 19 |
| 6 | NiBr2(dme) (10) | Cl | 30 | 2 | 10 |
| 7 | NiBr2(dme) (10) | Br | 30 | 15 | 52 |
| 8 | NiBr2(dme) (10) | I | 30 | 6 | 58 |
| 9 | NiBr2(dme) (10) | OTs | 30 | 17 | 68 |
| 10 | None | F | 25 | n.d. | n.d. |
| 11 | Pd(acac)2 (20) | F | 25 | n.d. | 52 |
| 12 | PtCl2 (20) | F | 25 | n.d. | 3 |
aReaction conditions: catalyst, n-OctF (1.0 mmol), p-F-C6H4MgBr (2.0 mmol), and 1,3-butadiene (3.0 mmol) in THF (3 mL) for 24 h.
bYields were determined by GC. Isolated yields are in parentheses.