Table 1.
Entry | Catalyst a | Substrate | Solvent | Temp | Time | Yield % (6/7/8) b |
---|---|---|---|---|---|---|
1 | Grubbs 1st generation | 5b | CH2Cl2 | rt | 24 h | 0 |
2 | Grubbs 1st generation | 5b | CH2Cl2 | reflux | 24 h | 0 |
3 | Grubbs 1st generation | 5b | 1,2-DCE | reflux | 24 h | 0 |
4 | Grubbs 1st generation | 5b | toluene | reflux | 24 h | 0 |
5 | Grubbs 2nd generation | 5b | CH2Cl2 | reflux | 24 h | Trace |
6 | Grubbs 2nd generation | 5b | toluene | reflux | 3 h | 54/14/8 |
7 | Grubbs 2nd generation | 5b | toluene | reflux | 24 h | 62/15/trace |
8 | Grubbs 2nd generation | 5b | neat | 80 °C | 24 h | Trace |
9 | Grubbs 2nd generation | 5a | CH2Cl2 | rt | 24 h | 0 |
10 | Grubbs 2nd generation | 5a | CH2Cl2 | reflux | 24 h | 0 |
11 | Grubbs 2nd generation | 5a | 1,2-DCE | reflux | 24 h | Trace |
12 | Grubbs 2nd generation | 5a | toluene | reflux | 24 h | 17/15/11 |
a5 mol % of the catalyst was used; bIsolated yield of products 6, 7, and 8.