Table 3.

Cross-Electrophile Coupling of 4-tert-Butyl-Bromobenzene with 1-Bromo-3-Phenylpropane with Varying Amounts of (dtbbpy)Ni^IIBr₂^a,b

entry	(dtbbpy)NiIIBr2 (X mol %)	product (%)	unreacted ArBr (%)	biphenyl (%)	unreacted AlkBr (%)c	catalytic regime
1d	0.1	55	29	<1	3	3
2d	0.5	68	22	<1	6	3
3	1	84	6	<1	<1	2
4e	2.5	66	4	9	10	1
5f	5	53	<1	12	30	1

^aReaction conditions: 1-bromo-4-tertbutylbenzene (0.0625 mmol), 1-bromo-3-phenylpropane (0.075 mmol), Co^II(Pc) (0.0016 mmol), and TDAE (0.075 mmol) in 1,4-dioxane (0.5 mL) at 80 °C for 24 h.

^bYields are reported as the average of two trials and were determined by integration of ¹H NMR spectra against a hexamethylbenzene external standard.

^cYield of recovered 1-bromo-3-phenylpropane reported relative to 4-tert-butyl-bromobenzene loading.

^dReaction run for 48 h.

^eReaction run for 12 h.

^fReaction run for 4 h.