Ni/Pd-catalyzed C–N cross-coupling reaction of aryl halides with amine and nitro precursors^a.

Entry	R1	X	R2 (amine or nitro)	Product	Time (h)		Yieldb (%)
					From amine	From nitroa,c	From amine	From nitro
1	H	I	H	19a	3	4.2	90	90
2	4-OH	I	H	19b	5	6.5	90	92
3	4-MeO	I	H	19c	6	7	94	96
4	4-Me	I	H	19d	3.5	4.8	92	96
5	4-CN	I	H	19e	2.2	3.5	96	96
6	H	I	4-OH	19b	2.6	4	95	97
7	H	I	4-MeO	19c	5.5	6.5	94	95
8	H	I	4-CN	19e	2	3.5	98	98
9	H	Br	H	19a	5	6.2	88	90
10	4-OH	Br	H	19b	6.5	7.7	80	80
11	4-MeO	Br	H	19c	7	8	82	85
12	4-Me	Br	H	19d	5	6.5	85	85
13	4-CN	Br	H	19e	3	4	90	86
14	H	Br	4-OH	19b	3	4.5	92	92
15	H	Br	4-MeO	19c	6.5	7.9	88	92
16	H	Br	4-CN	19e	4	5.4	80	85
17	H	Cl	H	19a	8.5	10	75	80
18	4-OH	Cl	H	19b	9	10.5	80	76
19	4-MeO	Cl	H	19c	12	14	66	60
20	4-Me	Cl	H	19d	9	11	75	75
21	4-CN	Cl	H	19e	8.5	10	70	65
22	H	Cl	4-OH	19b	8	9	76	80
23	H	Cl	4-MeO	19c	7	8.5	75	80
24	H	Cl	4-CN	19e	8	9	75	84

^aReaction conditions: amine or nitro (1.0 mmol), aryl halide (1.0 mmol), catalyst 11 (2.0 mg, 0.026 mol% Pd, 0.068 mol% Ni), DMSO₂ (3.36 g, 35.7 mmol), and 120 °C.

^bIsolated yield.

^cNaBH₄ (2.0 mmol).