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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 10.

Comparison of the Activity of Josiphos CyPF-t-Bu Analogs for the Coupling of Heteroaryl Chloride with Primary Alkylamine.

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Entry Ligand Loading Temp. Time (h) Yield
1 CyPF-t-Bu 1 0.005 90 °C 24 93
2 PPF-t-Bu 4 1.0 90 °C 24 67
3 MePF-t-Bu 5 0.005 90 °C 24 < 5%
4 EtPF-t-Bu 6 0.005 90 °C 24 < 5%
5 CyPF-Cy 7 1.0 90 °C 24 46
6 CyPF-Ph 8 1.0 90 °C 24 48
7 tBuPF-Cy 9 0.005 90 °C 24 62
8 10 0.005 90 °C 24 50
9 11 0.001 100 °C 48 16
10 11 0.005 90 °C 24 93
11 12 0.005 90 °C 24 < 5%
12 13 0.005 90 °C 24 < 5%
13 14 0.005 90 °C 24 < 5%
14 15 0.005 90 °C 24 < 5%
15 16 0.005 90 °C 24 < 5%
16 17 0.005 90 °C 24 < 5%
graphic file with name nihms171850u13.jpg