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. 2022 Apr 11;18:381–419. doi: 10.3762/bjoc.18.43

Table 1.

Different approaches of 2-methylnaphthalene oxidation to menadione.

graphic file with name Beilstein_J_Org_Chem-18-381-i001.jpg

Entry Conditions Catalyst Yield (%) Ref.

1 CrO3, H2O, AcOH, 85–90 °C, 1 h 38–42 [47]
2 Na2Cr2O7·H2O, H2SO4, CCl4, 80 to 0 °C, 15 min 48–62 [48]
3 H5IO6, CH3CN, 5 °C, 1 h CrO3 61 [49]
4 H2O2 (60%), AcOH, 50 °C, 8 h palladium(II)-resin 50–60 [50]
5 H2O2 (85%), Ac2O, AcOH, 40 °C, N2, 4 h CH3ReO3 46 [51]
6 H2O2 (30%), AcOH, 100 °C, 3 h 86 [52]
7 H2O2 (0.2 M), AcOH, rt, 24 h iron(III) salts 13 [53]
8 H2O2 (30%), AcOH, 60 °C, 3 h MnPc 60 [54]
9 H2O2 (30%), TAA, rt, 1.5 h FeCl3·H2O/H2Pydic/benzylamine 44 [55]
10 H2O2, AcOH, 100 °C, 6 h SeMCM-41 99a [56]
11 H2O2 (30%), AcOH, H2SO4, 60–80 °C, 1 h [(DIPAPTES)PdCl2] or [SiO2(DIPAPES)PdCl2] 52 or 59 [57]
12 H2O2 (35%), CH3CN, AcOH, reflux, 8 h GO@CHONHRN(CH2PPh2)2PdCl2 99a [58]
13 H2O2 (35%), CH3CN, AcOH, H2SO4, reflux, 12 h L1-iron(III) 79a [59]
14 H2O2 (35%), CH3CN, H2O, 60 °C, 20 min H[CuII(ttb)(H2O)3]2[CuII(ttb)Cl]2
[PW12O40]·4H2O
78a [60]
15 CH3COOOH, AcOH, 80 °C, 2 h Au/HPS 72 [61]
16 O3, AcOH, 160 °C chromium(III) and manganese(II) salts 70 [62]

aConversion.