Table 2.
Substrate Scope of Hiyama Coupling Reactions
![]() | |||
---|---|---|---|
entrya | enaminone | product | yield (%)b |
1 |
![]() 1a |
![]() 3b |
85 |
2 |
![]() 1a |
![]() 3c |
73 |
3 |
![]() 1a |
![]() 3d |
50 |
4 |
![]() 1a |
![]() 3e |
65 |
5 |
![]() 1a |
![]() 3f |
61 |
6c |
![]() 1a |
![]() 3g |
43 |
7 |
![]() 1b |
![]() 3h |
62 |
8 |
![]() 1c |
![]() 3i |
81 |
9 |
![]() 1d |
![]() 3j |
75 |
10 |
![]() 1e |
![]() 3k |
68 |
11 |
![]() 1f |
![]() 3l |
72 |
12d |
![]() 1g |
not observed | 0 |
13d |
![]() 1h |
not observed | 0 |
Reaction conditions: enaminone (0.1 M), Pd(OAc)2 (0.25 equiv), CuF2 (2.5 equiv), ArSi(OEt)3 (2.5 equiv) in tBuOH/AcOH (4:1), 65 °C, 3h.
Isolated yield.
α-Naphthyltrimethoxysilane was used.
Starting material recovered.