One-Pot Monoterpene Alcohol Amination over Au/ZrO2 Catalyst: Effect of the Substrate Structure | Sciact - CRIS-system of Boreskov Institute of Catalysis

One-Pot Monoterpene Alcohol Amination over Au/ZrO2 Catalyst: Effect of the Substrate Structure Full article

Journal

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

Output data

Year: 2018, Volume: 360, Pages: 127-134 Pages count : 8 DOI: 10.1016/j.jcat.2018.01.020

Tags

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

Authors

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

Affiliations

1	Boreskov Institute of Catalysis, pr. Lavrentieva 5, 630090 Novosibirsk, Russia
2	Novosibirsk State University, Pirogova 2, 630090 Novosibirsk, Russia
3	Novosibirsk Institute of Organic Chemistry, pr. Lavrentieva 9, 630090 Novosibirsk, Russia
4	Universidad Nacional Autónoma de México, Centro de Nanociencias y Nanotecnología, km. 107 carretera Tijuana a Ensenada, C.P. 22860 Ensenada, BC, México
5	Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, FI-20500 Turku/Åbo, Finland

Funding (3)

1	Russian Foundation for Basic Research	16-33-60028
2	National Autonomous University of Mexico National Council of Science and Technology	179619
3	National Autonomous University of Mexico	203117

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.

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 ANCAN OpenAlex

Submitted:	Dec 13, 2017
Accepted:	Jan 19, 2018
Published online:	Feb 22, 2018
Published print:	Apr 1, 2018

Web of science:	WOS:000428823600014
Scopus:	2-s2.0-85042317477
Elibrary:	35501771
Chemical Abstracts:	2018:260780
Chemical Abstracts (print):	168:306519
OpenAlex:	W2793402714

DB	Citing
Web of science	25
Scopus	25
Elibrary	21
OpenAlex	25