One-pot monoterpene alcohol amination over Au/ZrO2 catalyst: Effect of the substrate structure

One-pot monoterpene alcohol amination over Au/ZrO2 catalyst: Effect of the substrate structure Научная публикация

Журнал

Journal of Catalysis
ISSN: 0021-9517 , E-ISSN: 1090-2694

Вых. Данные

Год: 2018, Том: 360, Страницы: 127-134 Страниц : 8 DOI: 10.1016/j.jcat.2018.01.020

Ключевые слова

One-pot alcohol amination; Gold; Substrate structure effect; Terpene alcohol; Biologically active compound

Авторы

Demidova Yu.S. ^1,2 , Suslov E.V. ³ , Simakova I.L. ^1,2 , Mozhajcev E.S. ³ , Korchagina D.V. ³ , Volcho K.P. ^2,3 , Salakhutdinov N.F. ^2,3 , Simakov A. ⁴ , Murzin D.Yu. ⁵

Организации

1	(Данные Web of science) Boreskov Inst Catalysis, Pr Lavrentieva 5, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk Organ Chem Inst, Pr Lavrentieva 9, Novosibirsk 630090, Russia
4	(Данные Web of science) Univ Nacl Autonoma Mexico, Ctr Nanociencias & Nanotecnol, Km 107 Carretera Tijuana Ensenada, Ensenada 22860, BC, Mexico
5	(Данные Web of science) Abo Akad Univ, Proc Chem Ctr, Biskopsgatan 8, FI-20500 Turku, Finland

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.

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

Опубликована в печати:

1 апр. 2018 г.

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