Table 2.

Optimization of the Ligand/Palladium Combination for the Cross Coupling of K⁺9^- with 16a.^a

entrya	Pd source, 5 mol% Pd	ligand, 1/1 Pd/L	time, h	conversion, %b	product yield, %c
1	Pd(dba)2	Ph3P(O)	7	24	7
2	(C3H5)CpPd	dppp	20	100	30
3	PdCl(C3H5)(Ii-Pr)	-	20	43	10
4	(Ph3P)4Pd	-	20	68	37
5	[allylPdCl]2	-	7	37	9
6	[allylPdCl]2	dppp(O)2	7	95	45
7	[allylPdCl]2	dppp(O)	7	54	30
8	[allylPdCl]2	dppp	3	69	51
9	[allylPdCl]2	Ph3As	7	22	12
10	[allylPdCl]2	SPhos	7	71	46
11	[allylPdCl]2	t-Bu3P	5.5	99 (100)d	79 (89)d
12	[allylPdCl]2	t-Bu3P•HBF4	20	88	68
13	18	-	7	90	73
14	(t-Bu3P)2Pd (19)	-	5	100 (100)e	88 (92)e

^aReactions conditions: 1.5 equiv of arylsilanolate K⁺9^- and 1.0 equiv of 16a

^bConversion was based on consumption of aryl bromide as determined by GC analysis using an internal standard.

^cYield determined by GC analysis using an internal standard.

^dYield in parentheses based on 2:1 ratio of ligand/Pd.

^eConversion and yield in parentheses refers to the use of (t-Bu₃P)₂Pd purchasedfrom Aldrich Chemical Co.