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Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides. / Shutovskaya, Evgeniya S.; Ustimenko, Yulia P.; Tkachev, Alexey V. et al.

In: Advanced Synthesis and Catalysis, Vol. 365, No. 23, 2023, p. 4256-4266.

Research output: Contribution to journal › Article › peer-review

Harvard

Shutovskaya, ES, Ustimenko, YP, Tkachev, AV, Burykina, JV, Agafontsev, AM, Lastovka, AV, Polovyanenko, DN & Sukhikh, TS 2023, 'Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides', Advanced Synthesis and Catalysis, vol. 365, no. 23, pp. 4256-4266. https://doi.org/10.1002/adsc.202300594

APA

Shutovskaya, E. S., Ustimenko, Y. P., Tkachev, A. V., Burykina, J. V., Agafontsev, A. M., Lastovka, A. V., Polovyanenko, D. N., & Sukhikh, T. S. (2023). Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides. Advanced Synthesis and Catalysis, 365(23), 4256-4266. https://doi.org/10.1002/adsc.202300594

Vancouver

Shutovskaya ES, Ustimenko YP, Tkachev AV, Burykina JV, Agafontsev AM, Lastovka AV et al. Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides. Advanced Synthesis and Catalysis. 2023;365(23):4256-4266. doi: 10.1002/adsc.202300594

Author

Shutovskaya, Evgeniya S. ; Ustimenko, Yulia P. ; Tkachev, Alexey V. et al. / Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides. In: Advanced Synthesis and Catalysis. 2023 ; Vol. 365, No. 23. pp. 4256-4266.

BibTeX

@article{a44c9ab598ad4048a717129931a63148,
title = "Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides",
abstract = "Herein we describe Pd-catalyzed cross-coupling reaction of α-pinene derivative – pinacarvone O-methyl oxime (1) with aryl halides (2). Surprisingly, the formation of the C−C coupling product was accompanied by an unexpected opening of the pinene bicyclic structure. The (Z)-2-aryl-4,4,5-trimethylcyclohexa-2,5-dien-1-one O-methyl oxime (3) was formed as the resulting product. The reaction conditions of the developed synthetic procedure were carefully optimized and the reaction mechanism was supposed on the basis of data obtained by structural and computational methods.",
keywords = "Cross-coupling, Heck reaction, bicyclic terpene, palladium catalyst, ring opening",
author = "Shutovskaya, {Evgeniya S.} and Ustimenko, {Yulia P.} and Tkachev, {Alexey V.} and Burykina, {Julia V.} and Agafontsev, {Alexander M.} and Lastovka, {Anastasiya V.} and Polovyanenko, {Dmitriy N.} and Sukhikh, {Taisiya S.}",
note = "The reported study was funded by RFBR according to the research project No 19-33-50081 mol_nr. The study wass upported by the Ministry of Science and Higher Education of the Russian Federation projects 122040400035-3 (Yu.P. Usti-menko, A.M. Agafontsev, A.V. Tkachev) and 122040400029-2 (A.V. Lastovka, D.N. Polovyanenko). The authors would like to acknowledge the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements and the Information Technology Center of Novosibirsk State University for providing access to the cluster computational resources to carry out quantum-chemical calculations. Authors thank Dr. A.Kashin for SEM-EDX study and helpful discussions. Authors highly appreciate contributionof Prof. Dr. Valentine P. Ananikov during project development. Публикация для корректировки.",
year = "2023",
doi = "10.1002/adsc.202300594",
language = "English",
volume = "365",
pages = "4256--4266",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4169",
publisher = "Wiley-VCH Verlag",
number = "23",

}

RIS

TY - JOUR

T1 - Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides

AU - Shutovskaya, Evgeniya S.

AU - Ustimenko, Yulia P.

AU - Tkachev, Alexey V.

AU - Burykina, Julia V.

AU - Agafontsev, Alexander M.

AU - Lastovka, Anastasiya V.

AU - Polovyanenko, Dmitriy N.

AU - Sukhikh, Taisiya S.

N1 - The reported study was funded by RFBR according to the research project No 19-33-50081 mol_nr. The study wass upported by the Ministry of Science and Higher Education of the Russian Federation projects 122040400035-3 (Yu.P. Usti-menko, A.M. Agafontsev, A.V. Tkachev) and 122040400029-2 (A.V. Lastovka, D.N. Polovyanenko). The authors would like to acknowledge the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements and the Information Technology Center of Novosibirsk State University for providing access to the cluster computational resources to carry out quantum-chemical calculations. Authors thank Dr. A.Kashin for SEM-EDX study and helpful discussions. Authors highly appreciate contributionof Prof. Dr. Valentine P. Ananikov during project development. Публикация для корректировки.

PY - 2023

Y1 - 2023

N2 - Herein we describe Pd-catalyzed cross-coupling reaction of α-pinene derivative – pinacarvone O-methyl oxime (1) with aryl halides (2). Surprisingly, the formation of the C−C coupling product was accompanied by an unexpected opening of the pinene bicyclic structure. The (Z)-2-aryl-4,4,5-trimethylcyclohexa-2,5-dien-1-one O-methyl oxime (3) was formed as the resulting product. The reaction conditions of the developed synthetic procedure were carefully optimized and the reaction mechanism was supposed on the basis of data obtained by structural and computational methods.

AB - Herein we describe Pd-catalyzed cross-coupling reaction of α-pinene derivative – pinacarvone O-methyl oxime (1) with aryl halides (2). Surprisingly, the formation of the C−C coupling product was accompanied by an unexpected opening of the pinene bicyclic structure. The (Z)-2-aryl-4,4,5-trimethylcyclohexa-2,5-dien-1-one O-methyl oxime (3) was formed as the resulting product. The reaction conditions of the developed synthetic procedure were carefully optimized and the reaction mechanism was supposed on the basis of data obtained by structural and computational methods.

KW - Cross-coupling

KW - Heck reaction

KW - bicyclic terpene

KW - palladium catalyst

KW - ring opening

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85176320395&origin=inward&txGid=b94f76c0973b42429f44a9998f91e3ed

UR - https://www.mendeley.com/catalogue/f57a0e82-bdc5-353a-b830-dd9a98efadfc/

U2 - 10.1002/adsc.202300594

DO - 10.1002/adsc.202300594

M3 - Article

VL - 365

SP - 4256

EP - 4266

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4169

IS - 23

ER -

ID: 59194231