Table 9.

Coupling of Functionalized Aryl Halides with Primary Amines Catalyzed by Pd(OAc)₂ and CyPF-t-Bu (1:1).^a

Entry	-FG	X	R	Cat. (%)	Conditions	Yieldb (%)
1	-4-COOH	Cl	Octyl	0.05	100 °C, 20 h	81
2		Br	Octyl	0.05	100 °C, 20 h	72
3		Br	secBu	0.05	100 °C, 20 h	92
4		I	secBu	0.05	100 °C, 48 h	78
5	-4-CONH2	Cl	isoBu	0.5	100 °C, 20 h	67
6		Br	isoBu	0.05	100 °C, 20 h	85
7c	-4-COCH3	Cl	Octyl	0.5	70 °C, 20 h	91
8d		Cl	Octyl	0.5	110 °C, 24 h	74
9		Cl	Octyl	0.05	100 °C, 16 h	61
10d		I	Octyl	1.0	110 °C, 24 h	78
11c		Cl	Cyclohexyl	0.5	70 °C, 20 h	87
12d		Br	Cyclohexyl	1.0	110 °C, 24 h	82
13	-4-NHCOCH3	Br	Octyl	0.05	100 °C, 20 h	98
14		I	Octyl	0.5	110 °C, 20 h	67
15	-3-NHCOCH3	Cl	Cyclohexyl	0.05	100 °C, 24 h	74
16	-4-CH2OH	Br	isoBu	0.05	100 °C, 48 h	72
17		I	isoBu	0.05	100 °C, 20 h	47
18	-4-CH(OH)CH3	Cl	secBu	0.5	100 °C, 18 h	83
19	-4-CH2CH2OH	Cl	Octyl	0.5	100 °C, 20 h	89
20	-3-OH	Cl	Bn	0.5	100 °C, 20 h	84
21		Br	Bn	0.5	100 °C, 20 h	85
22		Br	Cyclohexyl	0.5	100 °C, 36 h	81
23		I	Cyclohexyl	1.0	100 °C, 20 h	70
24	-4-OH	Cl	Octyl	2.0	100 °C, 18 h	72
25d	-4-CO2Me	Cl	isoBu	1.0	110 °C, 24 h	94
26d	-4-CO2Et	I	secBu	2.0	110 °C, 48 h	77
27d	-3-CO2Me	Cl	isoBu	1.0	110 °C, 24 h	91
28d		Br	isoBu	1.0	110 °C, 24 h	97
29d	-2-CO2Me	Cl	Bn	2.0	110 °C, 24 h	82
30d	-4-NO2	I	Octyl	1.0	110 °C, 24 h	79

^aReactions conducted with a 1:1 ratio of metal to ligand, 1.0 mmol ArX (X = Cl, Br, I), 1.2 equiv amine, and 2.4 equiv LiN(SiMe₃)₂ in 1 mL DME.

^bIsolated yields.

^cReactions run at 0.2 M.

^dUsing K₃PO₄ as the base.