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

Общее Language: Английский, Genre: Full article,
Status: Published, Source type: Original
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 National Autonomous University of Mexico
National Council of Science and Technology
179619
2 Russian Foundation for Basic Research 16-33-60028
3 National Autonomous University of Mexico 203117

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 Auδ+ availability required for alcohol dehydrogenation. Propanol-2, introduced as a hydrogen donor, improved the yield of the target amine.
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 publication_identifier_short.wos_identifier_type publication_identifier_short.scopus_identifier_type publication_identifier_short.rinz_identifier_type
Dates:
Submitted: Dec 13, 2017
Accepted: Jan 19, 2018
Published online: Feb 22, 2018
Published print: Apr 1, 2018
Identifiers:
publication_identifier.wos_identifier_type WOS:000428823600014
publication_identifier.scopus_identifier_type 2-s2.0-85042317477
publication_identifier.rinz_identifier_type 35501771
publication_identifier.accession_number_identifier_type 2018:260780
publication_identifier.chemical_accession_number_identifier_type 168:306519
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