Table 1.

Cross-Electrophile Coupling of Iodobenzene and Benzyl Chloride with Varying Amounts of Co^II(Pc)^ab

entry	CoII(Pc) (X mol %)	product (%)	unreacted ArI (%)	biphenyl (%)	unreacted BnCl (%)c	catalytic regime
1	0	40	3	21	28	1
2	0.01	77	<1	6	16	1
3	0.1	90	5	2	4	2
4	0.25	87	4	2	<1	2
5	0.5	96	3	1	<1	2
6	1	90	4	2	<1	2
7	2.5	75	14	1	<1	3
8	5	62	21	1	<1	3

^aReaction conditions: iodobenzene (0.0625 mmol), benzyl chloride (0.075 mmol), (dtbbpy)Ni^IIBr₂(0.0044 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 benzyl chloride reported relative to iodobenzene loading.