C–H bond oxygenation
1 (ref. 60 )
Fe3 O4 MNPs (10 mol%)
Ethylbenzene (1 mmol), TBHP (70% aq., 0.5 mmol), T = 120 °C, time = 3 h
93
Acetophenone
2 (ref. 61 )
HKUST-1@Cu–CuFe2 O4 (15.0 mg)
Ethylbenzene (1 mmol), CH3 CN (5 mL), N -hydroxyphthalimide (10 mol%), T = 60 °C, 1 atm O2 , time = 9 h
93
Acetophenone
3 (ref. 62 )
Mn(OH)x /γ-Al2 O3 (0.03 mmol)
Ethylbenzene (40 mmol), O2 flow (5 mL min−1 ), benzoic acid (0.4 mmol), T = 135 °C, time = 24 h
74
Acetophenone
4 (ref. 63 )
FeVO4 /g-C3 N4 (50.0 mg) nanocomposites
Ethylbenzene (10 mmol), CH3 CN (6 mL), H2 O2 (25 mmol), T = 60 °C time = 4 h
91
Acetophenone
5 (ref. 64 )
Mn–N–C@SiO2 , (30 mg)
Ethylbenzene (10 mL), O2 (0.8 MPa), T = 120 °C time = 5 h
12
Acetophenone
6 (ref. 65 )
Ruthenium complex (0.004 mmol)
Ethylbenzene (4 mmol), TBHP (12 mmol), T = 40 °C time = 26 h
82
Acetophenone
7 (ref. 66 )
Mn@SiO2 /Al2 O3 , mixed oxide (50.0 mg)
Ethylbenzene (1.14 mL, 2 mmol), TBHP 80% (1.34 mL, 2 mmol), T = 80 °C time = 24 h
67
Acetophenone
8 this work
Fe3 O4 @SiO2 -APTES-Fe2 LDAR (30.0 mg, 0.9 mol%)
Ethylbenzene (1 mmol), H2 O (1 mL), RT, time = 15 h, O2
100
Acetophenone
C
Created by potrace 1.16, written by Peter Selinger 2001-2019
C bond oxidative cleavage
9 (ref. 67 )
SiRu(H2 O)W11 O39 ((C6 H13 )4 N)5 (0.2 mol%)
Cyclohexene (1 mmol), 5 equiv. KHSO5 , 1,2-dichloroethane/H2 O 1 : 1, time = 4 h, T = 60 °C
67
Adipic acid
10 (ref. 68 )
WO(O2 )2 L2 2− (L = oxalic acid), (1 mol%)
Cyclohexene (0.3 mmol), 30% H2 O2 (134 mL), time = 24 h, T = 94 °C
96
Adipic acid
11 (ref. 69 )
Cu-salen-PPh3 , (8 mmol)
Cyclohexene (1 mmol), 2.6 equiv. 30% H2 O2 , H3 PO4 , [Emim]PF6 CH2 Cl2 (1 : 1), time = 3 h
96
Cyclohexen oxide
12 (ref. 70 )
C-PMAn -V, (27–38 wt%) (30.0 mg)
Cyclohexene (1 mmol), 8 equiv. TBHP, H2 O, time = 32 h, T = 105 °C
67
Adipic acid
13 (ref. 71 )
POM on oxide supports (50 wt%)
Cyclohexene (1 mmol), 3–4 equiv. 30% H2 O2 , 2-methylpropan-2-ol, time = 24 h, T = 60 °C
90
Adipic acid
14 (ref. 72 )
Ru on charcoal, (1 mol%)
Cyclohexene (1 mmol), 1.1 equiv. NaIO4 , MeCN : EtOAc : H2 O 1 : 1 : 1 (v/v), time = 7.5 h
42
Adipic acid
15 this work
Fe3 O4 @SiO2 -APTES-Fe2 LDAR (50.0 mg, 1.5 mol%)
Cyclohexene (2 mmol), H2 O (2 mL), NaSO3 (2 mmol), RT, time = 24 h, O2
87
Adipic acid
Benzoxazole synthesis
16 (ref. 73 )
(FeLAPIP )2 O (1.2 mol%)
Bromo aminophenol (1 mmol), TBHP (70%, 0.4 mL), H2 O (5 mL), time = 8 h
83
4,6-Di-tert -butyl-2-(4-boromophenyl)-1H -benzo[d ]oxazole
17 (ref. 74 )
Fe(iii )-salen (3 mol%)
3-Bromobenzaldehyde (1 mmol), EtOH (5 mL), T = 50 °C, time = 5 h
80
4,6-Di-tert -butyl-2-(3-boromophenyl)-1H -benzo[d ]oxazole
18 (ref. 75 )
RuCl3
4-Bromobenzaldehyde (1 mmol), [bmim]BF4 1 mL, T = 80 °C, time = 10 h
78
4,6-Di-tert -butyl-2-(4-boromophenyl)-1H -benzo[d ]oxazole
19 this work
Fe3 O4 @SiO2 -APTES-Fe2 LDAR (40.0 mg, 1.2 mol%)
4-Bromobenzaldehyde (1 mmol), H2 O (7 mL), T = 70 °C, time = 10 h
97
4,6-Di-tert -butyl-2-(4-boromophenyl)-1H -benzo[d ]oxazole