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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 3. Amination of Functionalized Aryl halides with Primary Alkylamine Using (CyPF-tBu)PdCl2 1a.

graphic file with name nihms90921u4.jpg
entry halide product catalyst loading (%) conditions yield (%)b
1 graphic file with name nihms90921t33.jpg graphic file with name nihms90921t34.jpg 0.05 100 °C 48 h 84
2 graphic file with name nihms90921t35.jpg graphic file with name nihms90921t36.jpg 0.5 100 °C 36 h 52
3c graphic file with name nihms90921t37.jpg graphic file with name nihms90921t38.jpg 0.5 110 °C 24 h 67
4 graphic file with name nihms90921t39.jpg graphic file with name nihms90921t40.jpg 0.5 100 °C 24 h 77
5 graphic file with name nihms90921t41.jpg graphic file with name nihms90921t42.jpg 0.5 100 °C 24 h 69
6 graphic file with name nihms90921t43.jpg graphic file with name nihms90921t44.jpg 0.05 100 °C 24 h 84
7 graphic file with name nihms90921t45.jpg graphic file with name nihms90921t46.jpg 0.05 100 °C 24h 78
8c graphic file with name nihms90921t47.jpg graphic file with name nihms90921t48.jpg 1.0 110 °C 24 h 75
9c graphic file with name nihms90921t49.jpg graphic file with name nihms90921t50.jpg 0.5 110 °C 24 h 88
10c graphic file with name nihms90921t51.jpg graphic file with name nihms90921t52.jpg 2.0 110 °C 48h 71
11c graphic file with name nihms90921t53.jpg graphic file with name nihms90921t54.jpg 1.0 110 °C 24 h 85
12c graphic file with name nihms90921t55.jpg graphic file with name nihms90921t56.jpg 1.0 110 °C 24 h 89
a

Reactions conducted with a 1:1 ratio of metal to ligand, 1 mmol ArX, 1.2 equiv amine, and 2.4 equiv LiN(SiMe3)2 in 1 mL DME.

b

Isolated yield.

c

Using K3PO4 as the base.