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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 8.

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

graphic file with name nihms171850u10.jpg

Entry Halide R Cat.
(%)
Yield
(%)b
1 graphic file with name nihms171850t1.jpg Bn 0.5 73
2 secBu 0.5 96
3 graphic file with name nihms171850t2.jpg Bn 0.5 59
4 isoBu 0.5 78
5 graphic file with name nihms171850t3.jpg Octyl 0.5 53
6 graphic file with name nihms171850t4.jpg Cyclohexyl 0.5 67
7 graphic file with name nihms171850t5.jpg Octyl 0.5 79
8 Bn 0.5 55
a

Reactions conducted with a 1:1 ratio of metal to ligand 1 mmol ArCl, 1.2 equiv amine and 1.4 equiv LiN(SiMe3)2 in 1 mL DME.

b

Isolated yields.