Sciact
  • EN
  • RU

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

Journal Advanced Syntethys and Catalysis
ISSN: 1615-4150
Output data Year: 2023, Number: 365, Pages: 4256– 4 Pages count : DOI: 10.1002/adsc.202300594
Tags Cross-coupling; bicyclic terpene; Heck reaction; palladium catalyst; ring openin
Authors Shutovskaya Evgeniya S. 1 , Ustimenko Yulia P. 2 , Tkachev Alexey V. 2 , Burykina Julia V. 1 , Agafontsev Alexander M. 2 , Lastovka Anastasiya V. 2,3 , Polovyanenko Dmitriy N. 2 , Sukhikh Taisiya S. 3
Affiliations
1 Федеральное государственное бюджетное учреждение науки Институт органической химии им. Н.Д. Зелинского Российской академии наук
2 N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
3 Nikolaev Institute of Inorganic Chemistry of the Siberian Branch of the RAS

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.S. , Ustimenko Y.P. , Tkachev A.V. , Burykina J.V. , Agafontsev A.M. , Lastovka A.V. , Polovyanenko D.N. , Sukhikh T.S.
Unusual Ring Opening of Bicyclic Terpenes During Pd-Catalyzed Coupling with Aromatic Halides
Advanced Syntethys and Catalysis. 2023. №365. С.4256– 4. DOI: 10.1002/adsc.202300594 WOS Scopus РИНЦ
Dates:
Submitted: Jun 5, 2023
Published online: Nov 14, 2023
Published print: Nov 30, 2023
Identifiers:
Web of science WOS:001101827500001
Scopus 2-s2.0-85176320395
Elibrary 64400386
OpenAlex W4388044734
Altmetrics: