Table 22.
Catalysts for the copper-catalyzed aerobic oxidation of 3,5-di-tert-butylcatechol to 3,5-di-tert-butylquinone.
| Entry | Copper Complex | Conditions | yield (%) | Rate information | Ref |
|---|---|---|---|---|---|
| 1 |
|
O2, MeOH | kcat = 32400 h−1 | 913 | |
| 2 |
|
O2, MeOH | kcat = 7200 h−1 | 914 | |
| 3 |
|
O2, MeCN | kcat = 5470 h−1 | 915 | |
| 4 |
|
O2, MeOH | kcat = 12.4 h−1 | 916 | |
| 5 |
|
O2, MeOH | kcat = 941 h−1 | 917 | |
| 6 |
|
O2, 5% H2O, in MeOH | kcat = 5048 h−1 | 918 | |
| 7 |
|
O2, MeOH | kcat = 3800 h−1 | 919 | |
| 8 |
|
O2, MeOH | kcat = 3300 h−1 | 920 | |
| 9 |
|
O2, DMF | kcat = 3120 h−1 | 921 | |
| 10 |
|
O2, MeOH | kcat = 393 h−1 | 922 | |
| 11 |
|
O2, MeOH | kcat = 283 h−1 | 923 | |
| 12 |
|
MeOH, NaOMe, | 99% | TON = 216 h−1 | 924 |
| 13 |
|
O2, MeCN | kcat = 215 h−1 | 925 | |
| 14 |
|
O2, MeOH | kcat = 109 h−1 | 926 | |
| 15 |
|
O2, MeOH | kcat = 81 h−1 | 927 | |
| 16 |
|
O2, MeOH | kcat = 48 h−1 | 928 | |
| 17 |
|
O2, MeOH, 100 min | 68% conv | TON = 41 h−1 | 929 |
| 18 |
|
O2, MeOH | TON = 31.6 h−1 | 930 | |
| 19 |
|
O2, MeOH | kcat = 28.2 h−1 | 931 | |
| 20 |
|
O2, MeOH | kcat = 18 h−1 | 932 | |
| 21 |
|
O2, MeOH, 15 °C, 6 h | 100% | kcat = 16 h−1 | 933 |
| 22 |
|
O2 MeOH | TON = 1.3 h−1 | 934 | |
| 23 |
|
O2, DMF, 40 °C | kcat = 1.09 h−1 | 935 | |
| 24 |
|
O2 | not given | 936 | |
| 25 |
|
O2, MeOH | not given | 937 | |
| 26 |
|
O2, MeCN | kcat = 28908 h−1 | 938 | |
| 27 |
|
O2, MeOH | kcat = 2994 h−1 | 939 | |
| 28 |
|
O2, MeOH | kcat = 64 h−1 | 940 | |
| 29 |
|
O2, MeOH | kcat = 41.3 h−1 | 941 | |
| 30 |
|
O2, MeOH | TON = 41 h−1 | 942 | |
| 31 |
|
O2, MeOH | kcat = 28.2 h−1 | 943 | |
| 32 |
|
O2, MeOH | TON = 22 h−1 | 944 | |
| 33 |
|
O2, MeOH | TON = 21.5 h−1 | 945 | |
| 34 |
|
O2 sodium dodecyl sulfate, H2O | kcat = 12.6 h−1 | 946 | |
| 35 |
|
O2, MeOH | kcat = 12.4 h−1 | 947 | |
| 36 |
|
O2, MeOH | kcat = 6 h-2 | 948 | |
| 37 |
|
O2, MeOH, pH = 6.8 | kcat = 5.69 h−1 | 949 | |
| 38 |
|
O2, MeOH | kcat = 5.24 h−1 | 950 | |
| 39 |
|
−80 °C, CH2Cl2 | 95% | 951 | |
| 40 |
|
O2, KOH, MeOH | kobs = 0.0050 h−1 | 952 | |
| 41 |
|
O2, MeOH | not given | 953 | |
| 42 |
|
O2, MeOH | does not follow Michaelis-Menten | 954 | |
| 43 |
|
O2, MeOH | kcat = 6502 h−1 | 955 | |
| 44 |
|
O2, MeOH | kcat = 2804 h−1 | 956 | |
| 45 |
|
O2, NaOH, MeOH | kcat = 576 h−1 | 957 | |
| 46 |
|
O2, MeOH | kcat = 66 h−1 | 958 | |
| 47 |
|
O2, 70% MeCN in H2O | kcat = 1.8 h−1 | 959 | |
| 48 |
|
O2, MeOH/aq buffer pH = 5.0 | kcat = 1044 h−1 | 960 | |
| 49 |
|
O2, MeOH | kcat = 331 h−1 | 961 | |
| 50 |
|
O2, MeOH | kcat = 118 h−1 | 962 | |
| 51 |
|
O2 MeOH, pH=8.5 | kcat = 23.4 h−1 | 963 | |
| 52 |
|
O2, MeCN | kcat = 23 h−1 | 964 | |
| 53 |
|
O2, MeOH | kcat = 21.2 h−1 | 965 | |
| 54 |
|
O2, MeOH | kcat = 20.5 h−1 | 966 | |
| 55 |
|
O2, MeOH/aq buffer pH = 5.0 | kcat = 19.8 h−1 | 967 | |
| 56 |
|
O2, MeOH, pH=8 | kcat = 11.2 h−1 | 968 | |
| 57 |
|
O2, MeOH/aq buffer pH = 5.1 | kcat = 3 h−1 | 969 | |
| 58 |
|
O2, MeOH | not given | 970 | |
| 59 |
|
O2, MeCN | kcat = 900 h−1 | 971 | |
| 60 |
|
O2, MeOH | kcat = 214 h−1 | 972 | |
| 61 |
|
O2, MeOH | kcat = 189 h−1 | 973 | |
| 62 |
|
air, MeOH | kcat = 40.0 h−1 | 974 | |
| 63 |
|
O2, MeOH | kcat = 36.5 h−1 | 975 | |
| 64 |
|
O2, MeOH | kcat = 25.8 h−1 | 976 | |
| 65 |
|
O2, MeOH | kcat = 21.4 h−1 | 977 | |
| 66 |
|
O2, DMF | kcat = 4.31 h−1 | 978 | |
| 67 |
|
O2, MeCN | kcat = 3.19 h−1 | 979 | |
| 68 |
|
O2, DMF | kcat = 0.804 h−1 | 980 | |
| 69 |
|
O2, MeCN | TON = 36 h−1 | 981 | |
| 70 |
|
O2, MeOH | kcat = 24.2 h−1 | 982 | |
| 71 |
|
O2, MeOH/MeCN | 67% conv | TON = 12 h−1 | 983 |
| 72 |
|
air, DMF | kcat = 0.9511 h−1 | 984 | |
| 73 |
|
O2, MeOH, rt, 6 h | 65% conv | 985 | |
| 74 |
|
O2, MeOH | kcat = 10.1 h−1 | 986 | |
| 75 |
|
O2, 60% MeOH in H2O | kcat = 9.6 h−1 | 987 | |
| 76 |
|
O2, MeOH, pH = 9.0 | kcat = 9.36 h−1 | 988 | |
| 77 |
|
O2, NEt3, MeOH | TON = 174 h−1 | 989 | |
| 78 |
|
O2, NEt3, MeOH | TON = 137 h−1 | 990 | |
| 79 |
|
O2, MeOH, 48 h | 92.6% | kcat = 12.8 h−1 | 991 |
| 80 |
|
O2, MeOH | kcat = 2.4 h−1 | 992 |