Table 1. Trialkylphosphine Ligand Effects^(a).

Entry	Ligand	Cone Angle	2	3a	4	5a
1(b),(c)	PMe3·HBF4	11826a	0	0	98	2
2(b),(c)	PEt3·HBF4	13226a	0	0	92	8
3	P(t-Bu)2Me·HBF4	16126b	0	0	0	100
4	Pd[PMe(t-Bu)2]2	16126b	0	0	0	100
5	Pd[PCy3]2	17026a	1	2	1	96
6	PCy3	17026a	2	2	6	90
7	Pd[P(t-Bu)Cy2]2	17427	6	6	0	88
8	Pd[P(t-Bu)2Cy]2	17827	81	5	0	14
9	Pd[P(t-Bu)3]2	18226a	100	0	0	0
10(b)	P(t-Bu)3·HBF4	18226a	98	2	0	0

^(a)Conditions: 1.0 equiv 1a, 2.0 equiv 4-bromotoluene, 1.2 equiv NaOtBu, 1 mol % Pd₂(dba)₃, 4 mol % ligand, toluene (0.25 M), 110 °C. The product ratios refer to GC ratios of products 2-5 that have been corrected for GC response factor. All reactions proceed to completion unless otherwise noted.

^(b)The reaction was conducted with 1.4 equiv 4-bromotoluene.

^(c)The reaction proceeded to 80% conversion.