Table 3.

Coupling of ortho-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	4		83	>50:1
2		0.1	0.1	100	12		71	17:1
3		0.5	0.07	80	4		93	>50:1
4		0.1	0.1	100	12		84	>50:1
5		0.5	0.07	80	4		89	>50:1
6		0.1	0.1	100	12		82	>50:1
7		0.5	0.038	80	4		85	>50:1
8		0.1	0.1	100	12		95	>50:1
9		0.5	0.038	80	12		96	>50:1
10		0.1	0.1	100	24		99	>50:1
11		0.1	0.1	100	12		95	>50:1
12		0.5	0.1	80	15		88	>50:1
13		0.5	0.038	80	5		66	--

^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.