Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
One-pot monoterpene alcohol amination over Au/ZrO2 catalyst : Effect of the substrate structure. / Demidova, Yu S.; Suslov, E. V.; Simakova, I. L. и др.
в: Journal of Catalysis, Том 360, 01.04.2018, стр. 127-134.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - One-pot monoterpene alcohol amination over Au/ZrO2 catalyst
T2 - Effect of the substrate structure
AU - Demidova, Yu S.
AU - Suslov, E. V.
AU - Simakova, I. L.
AU - Mozhajcev, E. S.
AU - Korchagina, D. V.
AU - Volcho, K. P.
AU - Salakhutdinov, N. F.
AU - Simakov, A.
AU - Murzin, D. Yu
N1 - Publisher Copyright: © 2018 Elsevier Inc.
PY - 2018/4/1
Y1 - 2018/4/1
N2 - 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.
AB - 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.
KW - Biologically active compound
KW - Gold
KW - One-pot alcohol amination
KW - Substrate structure effect
KW - Terpene alcohol
KW - OXIDATION
KW - HYDROGENATION
KW - ACID
KW - MYRTENOL AMINATION
KW - FRAGMENTS
KW - AMINES
KW - CHEMICALS
KW - KINETICS
KW - DERIVATIVES
KW - PK(A)
UR - http://www.scopus.com/inward/record.url?scp=85042317477&partnerID=8YFLogxK
U2 - 10.1016/j.jcat.2018.01.020
DO - 10.1016/j.jcat.2018.01.020
M3 - Article
AN - SCOPUS:85042317477
VL - 360
SP - 127
EP - 134
JO - Journal of Catalysis
JF - Journal of Catalysis
SN - 0021-9517
ER -
ID: 10426530