Table 9.

Cross Coupling of Electron-Deficient Potassium Arylsilanolates with Aryl Bromides Using (t-Bu₃P)₂Pd.^a

entry	R	no.	aryl halide	no.	catalyst loading. mol %	time, h	product	yield, %
1	4-CO2t-Bu	K+15-		16n	2.5	6	28n	57d
2	4-CO2t-Bu	K+15-		16j	2.5	7	28j	69 d
3	4-CO2t-Bu	K+15-		16h	2.5	6	28h	79 d
4	4-[2-(1,3- dioxolane)]	K+7-		16a	5.0	3	29a	77 c
5	4-[2-(1,3- dioxolane)]	K+7-		16h	5.0	3	29h	77 d
6	4-Cl	K+10-		16n	2.5	3.5	30n	57 d
7	4-Cl	K+10-		16r	5	3.5	30r	60 d
8	4-Cl	K+10-		16c	5	3.5	30c	68 c
9	4-Cl	K+10-		16l	2.5	3.5	30l	42 d
10	4-Cl	K+10-		16s	2.5	3.5	30s	56 d
11	4-Cl	K+10-		16q	5.0	3.5	30q	61 c
12	2,6-Clb	Na+14-		16g	7.5	3	31g	68 e
13	2,6-Clb	Na+14-		16k	7.5	3	31k	76 d
14	2,6-Clb	Na+14-		16h	7.5	3	31h	70 e

^aReactions employed 1.5 equiv of arylsilanolate

^bReaction employed 2.0 equiv of arylsilanolate in THF

^cYields are for isolated, chromatographically homogeneous products.

^dYields are for analytically pure products.

^eProducts were determined to be >99% pure by ¹H NMR spectroscopy.