. Author manuscript; available in PMC: 2009 Sep 1.

Published in final edited form as: J Am Chem Soc. 2005 Jun 22;127(24):8644–8651. doi: 10.1021/ja0430346

Table 2. Effect of Other Monodentate Phosphine Ligands^(a).

Entry	Ligand	Cone Angle	2	3a	4	5a
1	t-Bu₂P(o-biphenyl) (10)		94	6	0	0
2	2-(Dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl		76	24	0	0
3	Cy₂P(o-biphenyl)		52	39	1	8
4	2-(Diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl (11)		56	40	2	2
5	P(o-tol)₃	194^26a	18	42	9	31
6	P[C₆H₄(m-CF₃)]₃	165^26c	4	31	32	33
7	P[C₆H₄(p-CF₃)]₃	145^26d	3	28	26	43
8	PPh₃	145^26a	3	9	55	33
9	P[C₆H₄(p-OMe)]₃	145^26c	0	5	59	36
10	P(2-furyl)₃		0	8	82	10
11	Ph₂PMe	136^26a	0	0	86	14
12^(b)	PhPMe₂	122^26a	0	0	92	8

^(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.

Table 2. Effect of Other Monodentate Phosphine Ligands(a).

Table 2. Effect of Other Monodentate Phosphine Ligands^(a).