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. Author manuscript; available in PMC: 2010 Feb 19.
Published in final edited form as: Org Lett. 2009 Feb 19;11(4):899–902. doi: 10.1021/ol802844z

Table 2.

Amidine Synthesis Using Primary Amines.a

entry primary amines 4-pentenyl-amidines yield [%]b
1 graphic file with name nihms91595t4.jpg graphic file with name nihms91595t5.jpg 9 ≥95
2 10 90
3 graphic file with name nihms91595t6.jpg graphic file with name nihms91595t7.jpg 11 73
4 graphic file with name nihms91595t8.jpg graphic file with name nihms91595t9.jpg 12 76
5 graphic file with name nihms91595t10.jpg graphic file with name nihms91595t11.jpg 13 67
6 14 85c
7 15 78d
8 16 54
9 graphic file with name nihms91595t12.jpg graphic file with name nihms91595t13.jpg 17 52
a

All reactions utilized ynamide 6, 5.0 mol % Pd(PPh3)4, 1.0 equiv K2CO3, 3.0 equiv RNH2, THF [conc = 0.05 M], 65 °C, 5–8 h.

b

Isolated yields.

c

1.0 equiv of amine was used.

d

Reaction time was 24 h.