Table 2.
entry | substrate | olefin | product | yieldb |
---|---|---|---|---|
1 | 4 | R = CH2NHTs | 67c | |
2 | 4 | R = CH2NHBoc | 99 | |
3 | 4 | R = (CH2)4OH | 95 | |
4 | 4 | R = (CH2)3OH | 99 | |
5 | 4 | R = (CH2)4OTBS | 90 | |
6 | 4 | R = (CH2)4OCH2Ph | 92 | |
7 | 4 | R = (CH2)3Br | 92 | |
8 | 4 | R = (CH2)4CO2Et | 99 | |
9 | 4 | 95d | ||
10 | CF3I | 90e,f | ||
11 | CF3I | 81e,f | ||
12 | 93 | |||
13 | 75 | |||
14 | CCl3Br | 87f | ||
15 | 99d | |||
16 | 84d |
Reaction conditions: 1 (1.0 mol %), haloalkane (2.0 equiv), and LiBr (2.0 equiv) in DMF/H2O (1:4).
Isolated yield (%) after purification on SiO2.
90% brsm.
dr 1:1.
Excess of haloalkane was used.
No LiBr added.