Table 2.

Optimization of Cross-Coupling Reaction Using Trialkylphosphonium Tetrafluoroborate Salts^a

entry	(Z)-1b (equiv)	ligand, mol %	concn (M)	conv,b %	yield γ-5a,b %	γ/αc
1d	1.5	9, 2.5	0.5	100	50	38:1
2d	1.5	10, 2.5	0.5	100	88	51:1
3	1.5	3, 2.5	0.5	100	94	>99:1
4	1.5	3, 2.5	0.25	92	85	>99:1
5	1.5	3, 2.5	1.0	100	99	>99:1
6	1.25	3, 2.5	1.0	69	67	>99:1
7	2.0	3, 2.5	1.0	100	96	>99:1
8e	1.5	3, 2.5	1.0	97	86	17:1
9f	1.5	3, 1.25	1.0	18	18	>99:1
10g	1.5	3, 5.0	1.0	100	99	>99:1
11	1.5	3, 5.0	1.0	93	91	>99:1
12	1.5	3, 10	1.0	89	88	>99:1
13h	1.5	3, 2.5	1.0	18	18	>99:1
14i	1.5	3, 2.5	1.0	100	93	>99:1

^aReactions performed on 0.1 mmol scale.

^bDetermined by GC analysis.

^cGC peak area ratio of crude reaction mixture.

^dAverage of 2 experiments.

^eAPC (1.25 mol %) used as the catalyst.

^fPd(dba)₂ (1.25 mol %).

^gPd(dba)₂ (5.0 mol %).

^h50 °C.

ⁱ90 °C.