Table 5: Oxidation of benzyl alcohol catalyzed by CrLA2 using an aqueous H2O2 in acetonitrile.
Entrya | Temp (°C) | Time (h) | Yield (%)b | Conversion (%) | Selectivity (%) | TONd | TOFe | |||
BAb | BZc | Side products | Ra | |||||||
1 | 60 | 1 | 25 | — | — | 75 | 25 | 100 | 12.5 | 12.5 |
2 | 2 | 29 | — | — | 71 | 29 | 100 | 14.5 | 7.25 | |
3 | 4 | 34 | — | — | 66 | 34 | 100 | 17 | 4.25 | |
4 | 6 | 22 | 14 | — | 64 | 36 | 61 | 11 | 1.83 | |
5 | 70 | 1 | 39 | — | — | 61 | 39 | 100 | 19.5 | 19.5 |
6 | 2 | 44 | — | — | 56 | 44 | 100 | 22 | 11 | |
7 | 4 | 49 | 1 | — | 50 | 54 | 91 | 24.5 | 6.13 | |
8 | 6 | 41 | 13 | — | 46 | 50 | 82 | 20.5 | 3.42 | |
9 | 80 | 1 | 53 | — | — | 47 | 58 | 100 | 26.5 | 26.5 |
10 | 2 | 70 | — | — | 30 | 77 | 100 | 35 | 17.5 | |
11 | 4 | 85 | — | — | 15 | 85 | 100 | 42.5 | 10.63 | |
12 | 6 | 69 | 21 | — | 10 | 81 | 85 | 34.5 | 5.75 | |
13 | 90 | 1 | 41 | 21 | — | 38 | 62 | 66 | 20.5 | 20.5 |
14 | 2 | 34 | 25 | 9 | 32 | 68 | 51 | 17 | 8.5 | |
15 | 4 | 25 | 29 | 17 | 29 | 71 | 35 | 12.2 | 3.13 | |
16 | 6 | 22 | 33 | 19 | 26 | 74 | 30 | 11 | 1.83 | |
17 | 100 | 1 | 29 | 31 | 7 | 33 | 67 | 43 | 14.5 | 14.5 |
18 | 2 | 21 | 40 | 15 | 24 | 76 | 28 | 10.5 | 5.25 | |
19 | 4 | 16 | 51 | 19 | 14 | 86 | 19 | 8 | 2 | |
20 | 6 | 13 | 57 | 23 | 7 | 93 | 14 | 6.5 | 1.08 | |
aThe oxidation of benzyl alcohol (R) (1.0 mmol) catalyzed by complex CrLA2 (0.02 mmol) with aqueous H2O2 (3.00 mL) in 10 mL acetonitrile for 1–6 h. bThe yield based on GC results, selectivity percentage of the target oxide product BA and the other product BZ. cThe other side products are mainly of BZ. dTON (turnover number) = ratio of moles of product (here oxide) obtained to the moles of catalyst. eThe corresponding TOF (turnover frequency) (TON/h) are shown in parentheses (mol (mol catalyst)−1 h−1). |