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One-pot monoterpene alcohol amination over Au/ZrO2 catalyst: Effect of the substrate structure
Journal of Catalysis ( IF 6.5 ) Pub Date : 2018-02-22
Yu. S. Demidova, E.V. Suslov, I.L. Simakova, E.S. Mozhajcev, D.V. Korchagina, K.P. Volcho, N.F. Salakhutdinov, A. Simakov, D. Yu. Murzin

One-pot amination of natural monoterpene alcohols was studied over Au/ZrO2 catalyst, focusing on the structure effect of substrates selected based on their pharmaceutical relevance. Bicyclic (myrtenol and nopol, bearing an unconjugated –OH group) and monocyclic (perillyl) alcohols were chosen for aniline amination under comparable conditions. Utilization of nopol resulted in a tenfold decrease in the reaction rate from that for myrtenol, increasing selectivity to the amine. The influence of secondary transformation was more noticeable for monocyclic perillyl alcohol with a conjugated –OH group. Myrtenol amination was explored with a range of aliphatic and aromatic amines, showing that the primary amine structure affected both the initial dehydrogenation rate and the selectivity to the desired amine. A good correlation was found between substrate structure and reactivity using the Hammett equation. The myrtenol consumption rate was tentatively proposed to be affected by the Auδ+ availability required for alcohol dehydrogenation. Propanol-2, introduced as a hydrogen donor, improved the yield of the target amine.



中文翻译:

Au / ZrO 2催化剂上的一锅单萜醇胺化:底物结构的影响

在Au / ZrO 2上研究了自然单萜醇的一锅胺化催化剂,着重于根据药物相关性选择的底物的结构效果。在可比较的条件下,选择了双环(myrtenol和nopol,带有一个未结合的–OH基)和单环(紫苏)醇进行苯胺胺化。诺泊酚的使用导致反应速率比肉豆蔻醇降低了十倍,从而增加了对胺的选择性。对于具有共轭-OH基团的单环紫苏醇,二次转化的影响更为明显。用一系列脂族和芳族胺研究了Myrtenol胺化反应,表明伯胺结构既影响了初始脱氢速度,又影响了对所需胺的选择性。使用Hammett方程发现底物结构与反应性之间具有良好的相关性。醇脱氢所需的δ+可用性。作为氢供体引入的丙醇2提高了目标胺的收率。

更新日期:2018-02-22
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