Table 1.

Ligand Optimization for the Selective Pd-catalyzed Arylation of NH₃.^a

entry	ligand	conv (%)b	yield of 1 (%)b	yield of 2 (%)b
1	L1	100	72	15
2c	L2	100	80	3
3	L3	100	89d	4d
4	L4	100	87	3
5	L5	100	80	4
6	L6	100	92d	2d
7	L7	100	76	16
8	L8	54	22	20
9	L9	43	28	7

^aConditions: PhCl (0.5 mmol), NH₃ (1.5 mmol), NaO^tBu (0.7 equiv), Pd₂(dba)₃ (1 mol %), ligand (5 mol %), dioxane (4 mL, 0.125 M), 80°C, 5 h.

^bDetermined by GC.

^c13 h.

^dAverage of two runs.