Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides. / Shutovskaya, Evgeniya S.; Ustimenko, Yulia P.; Tkachev, Alexey V. и др.
в: Advanced Synthesis and Catalysis, Том 365, № 23, 2023, стр. 4256-4266.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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