Table 3.
Scope studies in [2+2] cycloadditions involving 1.
| entrya | alkene | cycloadduct | time | yieldb |
|---|---|---|---|---|
|
|
|
|||
| 1 | Ar = 4-MePh | 1 h | 86% | |
| 2 | Ar = 3-MePh | 2.5 h | 86% | |
| 3 | Ar = 2-MePh | 1 h | 81% | |
| 4c | Ar = Ph | 1.5 h | 79% | |
| 5d | Ar = 4-FPh | 2.5 h | 78% | |
| 6 | Ar = 4-AcOPh | 3 h | 78% | |
| 7d | Ar = 4-(HOCH2)Ph | 2.5 h | 56% | |
| 8e | Ar = 4-(MeO2C)Ph | 4.5 h | 31% | |
| 9 |
|
|
2 h | 87%f |
| 10d |
|
|
3.5 h | 0% |
| 11 |
|
|
3.5 h | 67% |
| 12d |
|
|
2.5 h | 48%g |
| 13 |
|
|
4.5 h | 0% |
Reactions were irradiated with a 20 W compact fluorescent lightbulb at −15 °C using 0.25 mol% Ru(bpm)3(BArF)2, 1 equiv of 1, and 2 equiv of coupling partner.
Values reflect the average isolated yields from two reproducible experiments. Products isolated in >10:1 d.r. unless otherwise noted.
Alkene 1 added over 1 h.
Alkene 1 added over 2 h.
Alkene 1 added over 4 h.
9:1 d.r.
3:1 d.r.