Visible Light-directly Triggered Quantitative Oxidation of 9,10-dihydroanthracene to Anthraquinone by Molecular Oxygen under Normal Temperature and Pressure.

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ID: 81568
2020
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Abstract
The development of mild and efficient process for the selective oxygenation of organic compounds by molecular oxygen (O 2 ) can be one of the key technologies for synthesizing oxygenates. This paper discloses an atom-efficient synthesis protocol for the photo-oxygenation of 9,10-dihydroanthracene (DHA) by O 2 to anthraquinone (AQ), which can achieve quantitative AQ yield (100%) without any extra catalysts and additives under normal temperature and pressure. Also, 86.4% AQ yield is obtained even in air atmosphere. Furthermore, this protocol has a good compatibility for the photo-oxidation of several other compounds with a similar structure to DHA. Based on a series of control experiments and free radical quenching and EPR spin trapping results. The photo-oxygenation of DHA is likely initiated by its photo-excited state DHA* and the latter can activate O 2 to a superoxide anion radical (O 2 ⚫- ) via a transfer of its electron. Subsequently, this photo-oxidation is gradually dominated by the oxygenated product AQ as an active photo-catalyst, obtained from the oxidation of DHA by O 2 ⚫- , and it is accelerated with the rapid accumulation of AQ. The present photo-oxidation protocol gives a good example for the selective oxygenation based on the photo-excited substrate self-activated O 2 , which compliances well with 'green' chemistry ideals.
Reference Key
jiang2020visiblechemsuschem Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Dabo Jiang, Wenwei Hu, Mengke Chen, Zaihui Fu, Anqun Su, Bo Yang, Feng Mao, Chao Zhang, Yachun Liu, Dulin Yin
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Journal ChemSusChem
Year 2020
DOI
10.1002/cssc.201903549
URL
Keywords
photo-oxidation 9,10-dihydroanthracene anthraquinone molecular oxygen superoxide free radical

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