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. Author manuscript; available in PMC: 2017 Nov 9.
Published in final edited form as: Org Lett. 2008 Aug 21;10(18):4109–4112. doi: 10.1021/ol801615u

Table 2. Coupling of Aryl Halides with Primary Alkylamines Using (CyPF-tBu)PdCl2 1a.

graphic file with name nihms90921u3.jpg
entry halide product catalyst loading (%) conditions yield (%)b
1 graphic file with name nihms90921t17.jpg graphic file with name nihms90921t18.jpg 0.001 110 °C, 24 h 92
2 graphic file with name nihms90921t19.jpg graphic file with name nihms90921t20.jpg 0.01 110°C,24 h 85
3 graphic file with name nihms90921t21.jpg graphic file with name nihms90921t22.jpg 0.05 100°C,24 h 88
4 graphic file with name nihms90921t23.jpg graphic file with name nihms90921t24.jpg 0.005 80 °C, 36 h 86
5 graphic file with name nihms90921t25.jpg graphic file with name nihms90921t26.jpg 0.005 100°C,36 h 74
6c 0.005 110 °C, 12 h 87
7 graphic file with name nihms90921t27.jpg graphic file with name nihms90921t28.jpg 0.05 100°C,30 h 88
8 graphic file with name nihms90921t29.jpg graphic file with name nihms90921t30.jpg 0.05 100°C,24 h 96
9 graphic file with name nihms90921t31.jpg graphic file with name nihms90921t32.jpg 0.05 110 °C, 24 h 70
a

Reactions conducted with a 1:1 ratio of metal to ligand, 1 mmol ArX, 1.2 equiv amine, and 1.4 equiv NaO-tBu in 1 mL DME.

b

Isolated yield.