Table 3.

Effects of Catalyst and Additive on Cross-coupling of Aryl Bromides with n-C₁₀H₂₁ZnI.^a

entry	Ar-Br	catalyst	19 / 20 / 21b
1		PdCl2(PPh3)2	< 5% conv
2	18a	PdCl2(dppf)	7/91/2
3		PdCl2(PPh3)2 + TMEDAc	<1/99/0 (95%)d
4		PdCl2(PPh3)2	4/26/70
5	18b	PdCl2(dppf)	5/91/4
6		PdCl2(PPh3)2 + TMEDAc	<1/98/1 (93%)d

^aConditions: alkylzinc iodide (1.1 mmol, 1.0 M in THF), aryl bromide (1 mmol), Pd catalyst (2 mol %). Reactions were run at 0.33 M at 40 °C, 12 h for entries 1–3, and at rt, 20 h for entries 4–6.

^bby GC on crude material.

^c1.1 equiv.

^dIsolated yield.