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Visible-Light-Driven Aromatization Hydrogen Evolution by Organic Dye and Ni Complex
Acta Chimica Sinica ( IF 1.7 ) Pub Date : 2017-01-01 , DOI: 10.6023/a16080421
Xiaoju Wang , Kui Dong , Qiang Liu

Pyridine derivatives play an important role in curing and controlling mites, bacteria, weed and so on. Pyrimidine derivatives exist in a number of bioactive natural products, and they have anti-allergy, anti-cancer, anti-inflammatory, insecticidal and some other properties. 3,4-Disubstituted thiophenes not only are important units for the synthesis of natural products, but also serve as key components in some biologically active compounds and material chemistry. In modern society, we have the urgent demand for achieving our products atom economicly and environment-friendly. Under this background, "atom-economy" reactions have been drawing great attention from many chemists-and they have got many exciting improvements since then. So, we want to make our own contributions to this area and the following are some of our preliminary results. Our method was based on synergistic application of eosin Y with nickel (II) complex and an external oxidant-free oxidative dehydrogenation aromatization has been developed. At room temperature, Hantzsch 1,4-dihydropyridines, 1,4-dihydropyrimidines, 2,5-dihydrothiophenes and 2,5-dihydropyrroles were transformed into corresponding aromatic compounds in excellent yield under visible light irradiation via hydrogen evolution. We determined the hydrogen with GC-TCD using pure hydrogen as an external standard. It features very mild reaction conditions, high yields and excellent chemo-selectivity. In the previous reports, these transformations usually required higher temperatures and/or stronger oxidizing reagents, resulting in the generation of a large amount of by-products. In addition, the hydrogen evolution reactions were also compared with those of aerobic dehydrogenation. The results indicated that the dehydrogenation aromatizations of hantzsch 1,4-dihydropyridines and 1,4-dihydropyrimidine derivatives under the hydrogen evolution conditions proceeded in higher yields but very low conversions, while the reactions of 2,5-dihydrothiophenes and 2,5-dihydropyrroles gave higher conversions in the aerobic dehydrogenation conditions. So far, this is the first report using organic dye material combined with nickel (II) complexes to achieve dihydrogen dehydrogenation aromatization of heterocyclic compounds. Keywords eosin-Y; nickel complex; hydrogen evolution; aromatization

中文翻译:

有机染料和镍配合物的可见光驱动芳构化氢析出

吡啶衍生物在防治螨类、细菌、杂草等方面具有重要作用。嘧啶衍生物存在于许多具有生物活性的天然产物中,它们具有抗过敏、抗癌、抗炎、杀虫等特性。3,4-二取代噻吩不仅是合成天然产物的重要单元,而且还是一些生物活性化合物和材料化学的关键组分。在现代社会,我们迫切需要实现我们的产品既经济又环保。在此背景下,“原子-经济”反应引起了众多化学家的极大关注,并取得了许多令人振奋的改进。所以,我们想在这个领域做出自己的贡献,以下是我们的一些初步结果。我们的方法基于曙红 Y 与镍 (II) 络合物的协同应用,并开发了一种外部无氧化剂氧化脱氢芳构化。在室温下,Hantzsch 1,4-二氢吡啶、1,4-二氢嘧啶、2,5-二氢噻吩和2,5-二氢吡咯在可见光照射下通过析氢以优异的产率转化为相应的芳香族化合物。我们使用纯氢气作为外标,通过 GC-TCD 测定氢气。它具有非常温和的反应条件、高产率和优异的化学选择性。在之前的报道中,这些转变通常需要更高的温度和/或更强的氧化剂,导致产生大量副产物。此外,还对析氢反应与好氧脱氢反应进行了比较。结果表明,在析氢条件下,1,4-二氢吡啶和1,4-二氢嘧啶衍生物的脱氢芳构化反应产率较高,但转化率很低,而2,5-二氢噻吩和2,5-二氢吡咯的脱氢芳构化反应产率较高。在好氧脱氢条件下转化率更高。迄今为止,这是首次报道利用有机染料材料结合镍(II)配合物实现杂环化合物的二氢脱氢芳构化。关键词 eosin-Y; 镍络合物;析氢;芳构化 4-二氢嘧啶衍生物在析氢条件下产率较高但转化率非常低,而2,5-二氢噻吩和2,5-二氢吡咯在有氧脱氢条件下的反应转化率较高。迄今为止,这是首次报道利用有机染料材料结合镍(II)配合物实现杂环化合物的二氢脱氢芳构化。关键词 eosin-Y; 镍络合物;析氢;芳构化 4-二氢嘧啶衍生物在析氢条件下产率较高但转化率非常低,而2,5-二氢噻吩和2,5-二氢吡咯在有氧脱氢条件下的反应转化率较高。迄今为止,这是首次报道利用有机染料材料结合镍(II)配合物实现杂环化合物的二氢脱氢芳构化。关键词 eosin-Y; 镍络合物;析氢;芳构化 这是首次使用有机染料材料结合镍(II)配合物实现杂环化合物的二氢脱氢芳构化。关键词 eosin-Y; 镍络合物;析氢;芳构化 这是首次使用有机染料材料结合镍(II)配合物实现杂环化合物的二氢脱氢芳构化。关键词 eosin-Y; 镍络合物;析氢;芳构化
更新日期:2017-01-01
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