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Unusual Ring Opening of Bicyclic Terpenes during Pd‐catalyzed Coupling with Aromatic Halides Full article

Journal Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150
Output data Year: 2023, Volume: 365, Number: 23, Pages: 4256-4266 Pages count : 11 DOI: 10.1002/adsc.202300594
Authors Shutovskaya Evgeniya 1 , Ustimenko Yulia 2 , Tkachev Alexey 2 , Burykina Julia 1 , Agafontsev Alexander 2 , Lastovka Anastasiya 3,4 , Polovyanenko Dmitriy 2 , Sukhikh Taisiya 5
Affiliations
1 FSBIS N D Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, RUSSIAN FEDERATION
2 Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, RUSSIAN FEDERATION
3 N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry Siberian Branch of the Russian Academy of Sciences Prosp. Akad. Lavrentieva 9 Novosibirsk 630090 Russia
4 Novosibirsk State University Pirogov St. 2 Novosibirsk 630090 Russia
5 Nikolaev Institute of Inorganic Chemistry, RUSSIAN FEDERATION

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.
Cite: Shutovskaya E. , Ustimenko Y. , Tkachev A. , Burykina J. , Agafontsev A. , Lastovka A. , Polovyanenko D. , Sukhikh T.
Unusual Ring Opening of Bicyclic Terpenes during Pd‐catalyzed Coupling with Aromatic Halides
Advanced Synthesis & Catalysis. 2023. V.365. N23. P.4256-4266. DOI: 10.1002/adsc.202300594 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:001101827500001
≡ Scopus: 2-s2.0-85176320395
≡ OpenAlex: W4388044734
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