Abstract: 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 Au2+ availability required for alcohol dehydrogenation. Propanol-2, introduced as a hydrogen donor, improved the yield of the target amine. (C) 2018 Elsevier Inc. All rights reserved.

Cite: Demidova Y.S. , Suslov E.V. , Simakova I.L. , Mozhajcev E.S. , Korchagina D.V. , Volcho K.P. , Salakhutdinov N.F. , Simakov A. , Murzin D.Y.
One-pot monoterpene alcohol amination over Au/ZrO2 catalyst: Effect of the substrate structure
Journal of Catalysis. 2018. V.360. P.127-134. DOI: 10.1016/j.jcat.2018.01.020 WOS Scopus РИНЦ

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Published print:

Apr 1, 2018

Identifiers:

Web of science	WOS:000428823600014
Scopus	2-s2.0-85042317477
Elibrary	35501771
OpenAlex	W2793402714

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