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. Author manuscript; available in PMC: 2010 Feb 16.
Published in final edited form as: J Am Chem Soc. 2008 Apr 30;130(20):6586. doi: 10.1021/ja077074w

Table 6.

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

graphic file with name nihms171850u8.jpg
Entry Ar X Ar′ Cat
(%)		 Conditions Yield
(%)b
1 2-Py Cl 4-Tol 0.1 100 °C, 24 h 86
2 Br 4-Tol 0.05 60 °C, 48 h 95
3 Cl 1-Naphathyl 0.05 100 °C, 24 h 98
4 3-Py Cl 4-Tol 0.05 100 °C, 24 h 93
5 Cl 2-Anisyl 0.05 100 °C, 24 h 99
6 Cl 2-Py 0.5 100 °C, 24 h 97
7 Br 4-Anisyl 0.05 100 °C, 48 h 80
8 I 4-Anisyl 0.05 100 °C, 24 h 97
9 Br 2-Pyrimidyl 1.0 110 °C, 20 h 96
10 Br 2-Prazinyl 1.0 110 °C, 20 h 92
11c 1,3-Pyrimidyl-5- Br 4-Tol 1.0 100 °C, 48 h 52
12 4-isoQuinolinyl Br 4-Tol 0.05 100 °C, 38 h 84
13 Ph Cl 4-Tol 0.05 100 °C, 24 h 99
14 Br 4-Tol 0.005 110 °C, 20 h 95
15 Br 2-Py 1.0 100 °C, 30 h 81
16 Br 2-benzothiazolyl 1.0 100 °C, 36 h 62
17 4-Tol Cl 4-Anisyl 0.05 100 °C, 24 h 99
18 Br 4-Anisyl 0.05 100 °C, 48 h 97
19 3-Anisyl Cl 4-Anisyl 0.05 100 °C, 24 h 99
20 Br 4-Anisyl 0.05 100 °C, 48 h 94
21 2-Tol Br 4-Tol 0.05 100 °C, 48 h 96
22 I 4-Tol 0.05 100 °C, 24 h 99
23 2,5-DiMephenyl Br 4-Tol 0.5 100 °C, 48 h 89
24 2-Cyclohexylphenyl Br 4-Tol 0.05 100 °C, 48 h 89
a

Reactions conducted with a 1:1 ratio of metal to ligand, 1 mmol ArX (X = Cl, Br, I), 1.2 equiv amine and 1.4 equiv NaOtBu in 1 mL DME.

b

isolated yield.

c

Using K3PO4 as the base.