Table 1.

Cross-Coupling of Organozinc Reagents with Bromobenzene (Hayashi and coworkers, 1984)

Catalyst	Ra	Time (h)	Yield (%)b
			sec-BuPh	n-BuPh	Recovered PhBr
PdCl2(dppf)	sec-Bu	20	100	0	0
Pd(PPh3)4	sec-Bu	24	1	2	78
PdCl2(PPh3)2	sec-Bu	22	3	3	87
PdCl2(dppp)	sec-Bu	22	13	3	79
NiCl2(PPh3)2	sec-Bu	22	1	4	59
NiCl2(dppp)	sec-Bu	22	45	7	44
PdCl2(dppf)	n-Bu	22		100	0
PdCl2(PPh3)2	n-Bu	24		34	13
PdCl2(dppp)	n-Bu	24		66	0
PdCl2(dppb)	n-Bu	21		90	0
NiCl2(PPh3)2	n-Bu	21		42	22
NiCl2(dppp)	n-Bu	21		3	78

^a2.0 equiv zinc reagent was used;

^bGC yields