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Aerobic oxidation method of alcohols
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A technology for aerobic oxidation and alcohols, used in chemical instruments and methods, organic chemistry, compounds containing elements of group 3/13 of the periodic table, etc.
Inactive Publication Date: 2021-04-20
TSINGHUA UNIV
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On the other hand, although these mainstream catalytic systems have demonstrated strong oxidation capabilities, the development of an efficient and compatible aerobic oxidation system is still a long-term challenge for aerobic oxidation reactions.
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Embodiment 1
[0088] Embodiment 1, the oxidation of active primary alcohol
[0093] Mix o-quinone shown in Formula 5-1 with lanthanum iodide at a molar ratio of 2:1, stir evenly in acetonitrile at 35°C, and then add 50 molar equivalents (that is, 50 times the molar amount of lanthanum iodide) 1- For phenylpropanol, replace the reaction bottle with oxygen by pumping three times, react at 35°C for 2 hours, remove acetonitrile by rotary evaporation, and obtain methyl phenylpropionate: 70% through column chromatography. The specific reaction equation is as figure 2 shown.
[0094] The structure is confirmed as follows: 1 H NMR (400MHz, CDCl 3 )δ7.29(m,2H),7.21(m,3H),3.66(s,3H),2.97(t,J=7.8Hz,2H),2.65(t,J=7.8Hz,2H). 13 C NMR (100MHz, CDCl 3 )δ173.4, 140.6, 128.6, 128.4, 126.4, 51.7, 35.8, 31.0.
Embodiment 3
[0095] Embodiment 3, the oxidation of secondary alcohol
[0096] Mix o-quinone shown in Formula 5-1 with lanthanum iodide at a molar ratio of 2:1, stir evenly in acetonitrile at 35°C, and then add 100 molar equivalents (that is, 50 times the molar amount of lanthanum iodide) phenethyl alcohol , the reaction bottle was replaced with oxygen by pumping three times, and reacted at 35° C. for 1 hour, acetonitrile was removed by rotary evaporation, and acetophenone was obtained by column chromatography: 99%. The specific reaction equation is as image 3 shown.
[0097] The structure is confirmed as follows: 1 H NMR (400MHz, CDCl 3 )δ7.96(m,2H),7.58(m,1H),7.47(m,2H),2.60(s,3H). 13 C NMR (100MHz, CDCl 3 )δ198.2, 137.2, 133.2, 128.6, 128.6, 26.7.
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Abstract
The invention relates to an aerobic oxidation catalyst of an alcohol compound. The aerobic oxidation catalyst comprises IIIB group metal cations, an o-quinone compound and iodine anions, wherein the o-quinone compound is of an electron-rich structure and is stable in structure, and the alcohol compound is selected from one or two of primary alcohols and secondary alcohols. The amount of the catalyst used in the synthesis method can be reduced to 1 mol%, the catalytic efficiency is high, the reaction time is short, oxygen is used as a terminal oxidant, and the method is green and environmentally friendly.
Description
technical field [0001] This article involves but is not limited to an organic synthesis technique, especially an aerobic oxidation method of alcohols. Background technique [0002] Alcohol oxidation has always been the most basic but indispensable reaction in synthetic chemistry. It can introduce a carbonyl group into the molecule, and use the unique reactivity of the carbonyl group to introduce a variety of functional groups into the carbon skeleton or perform corresponding transformations. Numerous oxidation methods or oxidants have been used in alcohol oxidation so far, such as chromium reagents (PCC, PDC, etc.), activated DMSO, hypervalent iodine reagents (DMP, IBX, etc.), metal catalysts (Oppenauer oxidation, silver carbonate )Wait. These methods are applicable to different types of substrates and can efficiently oxidize alcohols under different conditions. However, these oxidants usually need to be added in excess or even a large excess to ensure the complete conver...
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