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One-pot monoterpene alcohol amination over Au/ZrO2 catalyst : Effect of the substrate structure. / Demidova, Yu S.; Suslov, E. V.; Simakova, I. L. et al.

In: Journal of Catalysis, Vol. 360, 01.04.2018, p. 127-134.

Research output: Contribution to journalArticlepeer-review

Harvard

Demidova, YS, Suslov, EV, Simakova, IL, Mozhajcev, ES, Korchagina, DV, Volcho, KP, Salakhutdinov, NF, Simakov, A & Murzin, DY 2018, 'One-pot monoterpene alcohol amination over Au/ZrO2 catalyst: Effect of the substrate structure', Journal of Catalysis, vol. 360, pp. 127-134. https://doi.org/10.1016/j.jcat.2018.01.020

APA

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. (2018). One-pot monoterpene alcohol amination over Au/ZrO2 catalyst: Effect of the substrate structure. Journal of Catalysis, 360, 127-134. https://doi.org/10.1016/j.jcat.2018.01.020

Vancouver

Demidova YS, Suslov EV, Simakova IL, Mozhajcev ES, Korchagina DV, Volcho KP et al. One-pot monoterpene alcohol amination over Au/ZrO2 catalyst: Effect of the substrate structure. Journal of Catalysis. 2018 Apr 1;360:127-134. doi: 10.1016/j.jcat.2018.01.020

Author

Demidova, Yu S. ; Suslov, E. V. ; Simakova, I. L. et al. / One-pot monoterpene alcohol amination over Au/ZrO2 catalyst : Effect of the substrate structure. In: Journal of Catalysis. 2018 ; Vol. 360. pp. 127-134.

BibTeX

@article{01947336a80043bfb59db1abe466342d,
title = "One-pot monoterpene alcohol amination over Au/ZrO2 catalyst: Effect of the substrate structure",
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.",
keywords = "Biologically active compound, Gold, One-pot alcohol amination, Substrate structure effect, Terpene alcohol, OXIDATION, HYDROGENATION, ACID, MYRTENOL AMINATION, FRAGMENTS, AMINES, CHEMICALS, KINETICS, DERIVATIVES, PK(A)",
author = "Demidova, {Yu S.} and Suslov, {E. V.} and Simakova, {I. L.} and Mozhajcev, {E. S.} and Korchagina, {D. V.} and Volcho, {K. P.} and Salakhutdinov, {N. F.} and A. Simakov and Murzin, {D. Yu}",
note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Inc.",
year = "2018",
month = apr,
day = "1",
doi = "10.1016/j.jcat.2018.01.020",
language = "English",
volume = "360",
pages = "127--134",
journal = "Journal of Catalysis",
issn = "0021-9517",
publisher = "Academic Press Inc.",

}

RIS

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