Skip to main content
. Author manuscript; available in PMC: 2008 Dec 20.
Published in final edited form as: Org Lett. 2007 Nov 29;9(26):5477–5480. doi: 10.1021/ol702401w

Table 4.

Carboamination of aliphatic imides and amides.a

entry substrate product(s) yieldb(selectivity)
1 graphic file with name nihms63568t17.jpg
17 		graphic file with name nihms63568t18.jpg
18 		81%
2c,d graphic file with name nihms63568t19.jpg
19 		graphic file with name nihms63568t20.jpg
20 		graphic file with name nihms63568t21.jpg
21 		70%(20:21 = 1.6:2)
3c,e graphic file with name nihms63568t22.jpg
22 		graphic file with name nihms63568t23.jpg
23 		graphic file with name nihms63568t24.jpg
24 		83%(23:24 = 3.3:1)
4c,e graphic file with name nihms63568t25.jpg
25 		graphic file with name nihms63568t26.jpg
26 		graphic file with name nihms63568t27.jpg
27 		79%(26:27 = 3.4:1)
5c graphic file with name nihms63568t28.jpg
28 		graphic file with name nihms63568t29.jpg
29 		56%
6 graphic file with name nihms63568t30.jpg
30 		graphic file with name nihms63568t31.jpg
31 		81%
7c graphic file with name nihms63568t32.jpg
32 		graphic file with name nihms63568t33.jpg
33 		74%
a

Conditions. Substrate in DMF (0.1 M) was treated with Cu(EH)2 (3 equiv) and Cs2CO3 (1 equiv). The mixture was heated to 120 °C for 24 h in a pressure tube.

b

Yields refer to the sum of products isolated by chromatography on SiO2. The remainder of the material was either starting olefin or olefin-isomerized starting material.

c

Heated to 190 °C.

d

Reaction run for 72 h.

e

tbutyl benzene was used as solvent.