Table 2. The four-component coupling reaction of n-Oct–F, o-TolMgBr, and 1,3-butadiene.

Entry	Catalyst (mol%)	2j	Temp. (°C)	3aj (%) a
1	NiBr2(dme) (10)	2.0 equiv.	30	92
2	NiCl2(PPh3)2 (10)	2.0 equiv.	30	43
3	NiCl2(dppf) (10)	2.0 equiv.	30	8
4	NiCl2 (10)	2.0 equiv.	30	90
5	Ni(acac)2 (10)	2.0 equiv.	30	95
6	NiBr2(dme) (10)	1.5 equiv.	30	88
7	NiBr2(dme) (5)	1.5 equiv.	30	79
8	NiBr2(dme) (5)	1.5 equiv.	40	87 (86)

^aDetermined by GC (isolated yield is in parentheses). In all cases, ca. 5% of 4aj was observed in the GC analysis.