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. Author manuscript; available in PMC: 2012 Jun 17.
Published in final edited form as: J Org Chem. 2011 May 24;76(12):5092–5103. doi: 10.1021/jo200780x

Table 4.

Vinylogous Amidine Synthesis.

entry ynamides enaminesa vinylogous amidines yield [%]b
1 graphic file with name nihms296704t41.jpg 8a: R = Ts
8h: R = MBS
graphic file with name nihms296704t42.jpg 41 graphic file with name nihms296704t43.jpg 45
46
52c
2 71d
3 graphic file with name nihms296704t44.jpg 8f graphic file with name nihms296704t45.jpg 42 graphic file with name nihms296704t46.jpg 47 58e
4 graphic file with name nihms296704t47.jpg 8d graphic file with name nihms296704t48.jpg 41 graphic file with name nihms296704t49.jpg 48 54f
5 graphic file with name nihms296704t50.jpg8i graphic file with name nihms296704t51.jpg 41 graphic file with name nihms296704t52.jpg 49 57g
6 graphic file with name nihms296704t53.jpg8j graphic file with name nihms296704t54.jpg 43 graphic file with name nihms296704t55.jpg 50 --
7 graphic file with name nihms296704t56.jpg 42 graphic file with name nihms296704t57.jpg 51 62h
a

Unless otherwise noted, all reactions utilized 3.0 equiv of the enamine, 5.0 mol% Pd2(dba)3, and 10.0 mol% of xantphos; and were run in THF [conc = 0.05 M].

b

Isolated yields.

c

2 h at 70°C.

d

2 h at 50 °C with 1.5 equiv of K2CO3.

e

12 h at 70°C with 1.5 equiv of 42; 2.0 mol % Pd2(dba)3; and 4.0 mol% of xantphos.

f

30 min at 50 °C.

g

2 h at RT.

h

2 h at 75 °C with 1.5 equiv of K2CO3 and 1.5 equiv of 44.