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A robust iron catalyst for the selective hydrogenation of substituted (iso)quinolones†
Chemical Science ( IF 8.4 ) Pub Date : 2018-09-06 00:00:00 , DOI: 10.1039/c8sc02744g
Basudev Sahoo 1, 2, 3 , Carsten Kreyenschulte 1, 2, 3 , Giovanni Agostini 1, 2, 3 , Henrik Lund 1, 2, 3 , Stephan Bachmann 4, 5, 6, 7 , Michelangelo Scalone 4, 5, 6, 7 , Kathrin Junge 1, 2, 3 , Matthias Beller 1, 2, 3
Affiliation  

By applying N-doped carbon modified iron-based catalysts, the controlled hydrogenation of N-heteroarenes, especially (iso)quinolones, is achieved. Crucial for activity is the catalyst preparation by pyrolysis of a carbon-impregnated composite, obtained from iron(II) acetate and N-aryliminopyridines. As demonstrated by TEM, XRD, XPS and Raman spectroscopy, the synthesized material is composed of Fe(0), Fe3C and FeNx in a N-doped carbon matrix. The decent catalytic activity of this robust and easily recyclable Fe-material allowed for the selective hydrogenation of various (iso)quinoline derivatives, even in the presence of reducible functional groups, such as nitriles, halogens, esters and amides. For a proof-of-concept, this nanostructured catalyst was implemented in the multistep synthesis of natural products and pharmaceutical lead compounds as well as modification of photoluminescent materials. As such this methodology constitutes the first heterogeneous iron-catalyzed hydrogenation of substituted (iso)quinolones with synthetic importance.

中文翻译:

用于取代(异)喹诺酮类选择性加氢的强力铁催化剂

通过应用N掺杂的碳改性的铁基催化剂,可以实现N-杂芳烃,特别是(异)喹诺酮的受控氢化。对于活性而言至关重要的是通过热解碳浸渍的复合物来制备催化剂,所述复合物是从乙酸铁(II)和N-吡啶并获得的。如通过TEM,XRD,XPS和拉曼光谱所证明的那样,合成材料由Fe(0),Fe 3 C和FeN x组成。在氮掺杂的碳基体中。这种坚固且易于回收的铁材料具有良好的催化活性,即使在存在可还原的官能团(例如腈,卤素,酯和酰胺)的情况下,也可以选择性氢化各种(异)喹啉衍生物。为了进行概念验证,这种纳米结构催化剂用于天然产物和药物铅化合物的多步合成以及光致发光材料的改性。这样,该方法学构成了具有合成重要性的取代的(异)喹诺酮的第一个多相铁催化的氢化反应。
更新日期:2018-09-06
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