Table 4.

Coupling of meta- and para-Substituted Aryl Bromides with Ammonia^a

entry	aryl bromide	loading (%)	concentration [M]	T [°C]b	t [h]	product	yield (%)c	A:Bd
1		0.5	0.038	80	6		88	19:1
2		0.5	0.038	80	5		78	--
3		0.5	0.038	80	5		98	--
4		0.5	0.038	80	5		99	>50:1
5		0.5	0.038	80	5		61	12:1
6		0.5	0.038	80	12		77	--
7		1.0	0.05	100	15		53	9:1
8		1.0	0.05	90	15		91	>50:1
9		0.5	0.038	80	12		60	--
10		0.5	0.05	80	12		64	--
11		2.0	0.05	100	12		79	>50:1

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

^bTemperature of bath.

^cIsolated yield after purification by flash column chromatography.

^dDetermined by ¹H NMR spectroscopy.