Unusual Ring Opening of Bicyclic Terpenes During Pd‐Catalyzed Coupling with Aromatic Halides-Reference-Cited by-同舟云学术

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

Published:2023-11-14 Issue:23 Volume:365 Page:4256-4266
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Shutovskaya Evgeniya S.¹^ORCID,Ustimenko Yulia P.²,Tkachev Alexey V.²,Burykina Julia V.¹,Agafontsev Alexander M.²,Lastovka Anastasiya V.²³,Polovyanenko Dmitriy N.²,Sukhikh Taisiya S.⁴

Affiliation:

1. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Leninsky Prospect 47 Moscow 119991 Russia

2. N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry Siberian Branch of the Russian Academy of Sciences Prosp. Akad. Lavrentieva 9 Novosibirsk 630090 Russia

3. Novosibirsk State University Pirogov St. 2 Novosibirsk 630090 Russia

4. Nikolaev Institute of Inorganic Chemistry Siberian Branch of the Russian Academy of Sciences Prosp. Akad. Lavrentieva 3 Novosibirsk 630090 Russia

Abstract

AbstractHerein 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.

Funder

Russian Foundation for Basic Research

Ministry of Science and Higher Education of the Russian Federation

Publisher

Wiley

Subject

General Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202300594

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