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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 7.

Coupling of Aryl Chlorides and Bromides with Secondary Amines Catalyzed by Pd(OAc)2 and CyPF-t-Bu (1:1).a

graphic file with name nihms171850u9.jpg
Entry Ar Amine Cat
(%)		 Conditions Yield
(%)b
1 2-Py N-Methyl-aniline 1.0 70 °C, 3 h 57
2 3-Py Morpholine 1.0 90 °C, 12 h 69
3 4-Py Di-4-anisidine 1.0 70 °C, 12 h 50
4 1-isoquinolinyl N-Me-aniline 1.0 70 °C, 10 h 84
5 Ph N-Me-aniline 0.05 100 °C, 48 h 56
6 Dibutylamine 0.5 100 °C, 24 h 69
7 Diphenylamine 0.5 100 °C, 20 h 86
8 4-Tol Morpholine 0.1 100 °C, 48 h 86
9 3-Anisyl Morpholine 0.05 100 °C, 48 h 82
a

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

b

isolated yield.