Table 1.
Intermolecular Hydroamination of Alkenes (120 psi) with Cyclic Ureas Catalyzed by a Mixture of (2a)AuCl (5 mol %) and AgOTf (5 mol %) in Dioxane at 100 °C.
entry | nucleophile | alkene | product | time (h) | yielda |
---|---|---|---|---|---|
![]() |
![]() |
![]() |
|||
1 | X = NMe (1) | R = H | 3 | 20 | 99 |
2 | R = Me | 62 | 97 | ||
3b | R = Et | 69 | 99 | ||
4 | R = (CH2)5Me | 24 | 38c | ||
5 | X = Nt-Bu | R = H | 40 | 80 | |
6 | X = O | R = H | 72 | 75 | |
![]() |
![]() |
![]() |
|||
7 | n = 1 | R = H | 20 | 95 | |
8 b | n = 1 | R = Me | 65 | 85 | |
9 | n = 1 | R = Et | 68 | 86d | |
10 b | n = 2 | R = H | 19 | 98 | |
11 | n = 2 | R = Me | 67 | 86 |
Isolated yield of >95% purity.
Catalyst loading = 10 mol %.
GC yield. 1-Octene loading = 10 equiv.
dr = 1:1.