Table 2.
| |||
---|---|---|---|
entry | substrate | product | yieldb |
1 | 71% | ||
2 | 1b, R = SES | 2b, R = SES | 55% |
3 | 1c, R = Ns | 2c, R = Ns | 51% |
4 | 1d, R = Ms | 2d, R = Ms | 50% |
5 | 73% | ||
6 | 22% | ||
7 | 43% | ||
8 | 83% | ||
8 | 1h, Ar = 4-F-Ph | 2h, Ar = 4-F-Ph | 81% |
9 | 1i, Ar = 4-MeO-Ph | 2i, Ar = 4-MeO-Ph | 85% |
10 | 55% |
Reaction conditions used: 1a (0.174 mmol, 1 equiv), Cu(eh)2 (0.026 mmol, 15 mol %), TEMPO (0.035 mmol, 20 mol %), toluene (1.74 mL) and O2 (1 atm, balloon).
Isolated yield after column chromatography
22% of the (Z)-isomer of 1f was recovered.
SES = 2-(trimethylsilyl)ethanesulfonyl, Ns = 4-nitrophenylsulfonyl, Ms = methane sulfonyl.