Table 2. Catalytic isomerization of α-vinylbenzyl alcohol into propiophenone by 1 and 2, including significant bibliographic results.
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|---|---|---|---|---|---|---|---|---|
| Catalyst | [Cat] mol% | t (h) | T (°C) | Solvent | Additive | TOFa (h−1) | Conversion (%) | Ref. |
| 1 | 1 | 8 | 70 | MeOH/H2O | — | 3.5 | 28 | This work |
| 1 | 1 | 8 | 80 | i PrOH/H2O | — | 5.5 | 44 | This work |
| 1 | 2 | 4 | 70 | MeOH/H2O | — | 3.1 | 25 | This work |
| 1 | 2 | 8 | 70 | MeOH/H2O | — | 2.6 | 41 | This work |
| 1 | 2 | 4 | 80 | i PrOH/H2O | — | 8.4 | 67 | This work |
| 1 | 2 | 8 | 80 | i PrOH/H2O | — | 6.2 | 99 | This work |
| 2 | 1 | 24 | 70 | MeOH/H2O | — | 1.7 | 40 | This work |
| 2 | 1 | 24 | 80 | i PrOH/H2O | — | 3.1 | 73 | This work |
| 2 | 2 | 4 | 80 | MeOH/H2O | — | 3.5 | 28 | This work |
| 2 | 2 | 8 | 80 | MeOH/H2O | — | 2.6 | 42 | This work |
| 2 | 2 | 1 | 80 | i PrOH/H2O | — | 34.5 | 69 | This work |
| 2 | 2 | 4 | 80 | i PrOH/H2O | — | 12.4 | >99 | This work |
| [Rh(COD)Cl]2 | 5 | 17 | 80 | H2O | MeO-TPPMS | 1.2 | 99 | 7 |
| [Rh(COD)Cl]2 | 5 | 18 | 80 | H2O | PTA NaOH | 1.1 | 99 | 7 |
| [Rh(COD)(CH3CN)2]BF4 | 2 | 0.08 | 23 | H2O | PTA NaOH | 594 | 99 | 7 |
| [RuCl2(mTHPA)(η6-C6H6)] | 1 | 0.75 | 75 | H2O | KOtBu | 129 | 97 | 12 |
| [RuCl2(η6-C6H5OCH2CH2OH)(P(OiPr)3)] | 1 | 10 | 75 | H2O | KOtBu | 600 | 99 | 62 |
| [{Ru(η3:η3-C10H16)(μ-Cl)Cl2}] | 5 | 1 | 75 | H2O | — | 20 | 99 | 62 |
| [{Ru(η3:η3-C10H16)(μ-Cl)Cl2}] | 5 | 0.25 | 75 | H2O/Cs2CO3 | — | 80 | 99 | 62 |
| [Ru(η3:η3-C10H16)(Cl)2(benzimidazole)] | 1 | 3 h | 50 | H2O | iPrNH2 KH2PO4 buffer | 33 | 99 | 67 |
| [Ru(η3:η3-C10H16)(Cl)2(benzimidazole)] | 1 | 0.25 | 75 | H2O | — | 396 | 99 | 65 |
| [Ru(η3:η3-C10H16)(Cl)2(pyrazole)] | 0.2 | 1 | 75 | H2O | — | 495 | 99 | 64 |
| [Ru(η3:η3-C10H16)Cl(κ2O,O–CH3CO2)] | 1 | 2.5 | 50 | H2O | MgSO4 KH2PO4 buffer | 39.6 | 99 | 66 |
| [Ru(η3:η3-C10H16)Cl(benzimidazole)] | 1 | 2.5 | 50 | H2O | MgSO4 KH2PO4 buffer | 39.6 | 99 | 66 |
| [Ru(η3:η3-C10H16)Cl(κ2O,O–CH3CO2)] | 1 | 0.08 | 75 | H2O | — | 1200 | 99 | 3 |
TOF = turn over frequency, N2, ROH/H2O (1 : 1) = 1 mL, % measured by 1H NMR.