Table 7.

Coupling of Ammonia with Aryl Tosylates^a

entry	aryl bromide	loading (%)	concentration [M]	T [°C]b	t [h]	product	yield (%)c	A:Bd
1		2	0.1	50	24		65	17:1
2		2	0.1	50	24		86	>50:1
3		2	0.05	50	24		67	>50:1
4		2	0.05	50	24		67	--e
5		2	0.05	50	24		55	--e

^aReactions conducted with 1:1 ratio of metal to ligand, 0.5 mmol aryl chloride, 5 mL of 0.5 M ammonia solution, 1.4 equiv NaO-t-Bu in 1,4-dioxane.

^bTemperature of bath.

^cIsolated yield after purification by flash column chromatography.

^dDetermined by ¹H NMR spectroscopy.

^eSelectivity was not determined due to overlapping resonances in the aromatic region of the ¹H NMR spectra of the crude reaction mixtures.