Table 2.
Hydroacyloxylation activity of Ru catalysts.
| ||||
|---|---|---|---|---|
| entry | catalyst | co-ligand | yield[a] | isomer ratio[b] (E)-23 : (Z)-23 : 24 |
| 1 | 14 | – | 96% | 61 : 36 : 3 |
| 2 | 15 | – | 1% | 24 : 74 : 2 |
| 3 | 16 | – | 41% | 68 : 25 : 7 |
| 4 | 16 | 11 | 29% | 24 : 72 : 4 |
| 5 | 17 | – | 39% | 35 : 59 : 6 |
| 6 | 18 | – | 25% | 43 : 50 : 7 |
| 7 | 18 | 11 | 35% | 31 : 66 : 3 |
| 8 | 19 | – | 79% | 46 : 42 : 12 |
| 9 | 19 | 11 | 71% | 12 : 88 : 0 |
| 10 | 20 | – | 64% | 68 : 24 : 8 |
| 11 | 20 | 11 | 85% | 22 : 70 : 8 |
| 12 | 21 [c] | – | 56% | 60 : 40 : 0 |
| 13 | 21 | 11 | 35% | 17 : 83 : 0 |
| 14 | 9 | – | 100% | 73 : 20 : 7 |
Combined yield of isomers (E)-23, (Z)-23, and 24, after chromatographic separation from other materials.
Vinylic ester isomers (E)-23, (Z)-23, and 24 were chromatographically inseparable. Isomer ratios were determined by 1H NMR integration of diagnostic alkene resonances in the product mixture, prior to chromatographic purification.
21=[CpRu(NCMe)3][PF6].