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Updated: Jul 19, 2026

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
Published on: February 27, 2017
Nickel-catalysed intramolecular alkene insertion into cyclobutanones
Masahiro Murakami1, Shinji Ashida
1Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto, 615-8510, Japan. murakami@sbchem.kyoto-u.ac.jp
A nickel(0) catalyst facilitates a novel reaction, converting 3-styrylcyclobutanones into benzobicyclo[2.2.2]octenones. This transformation involves the intramolecular insertion of a vinyl group into the cyclobutanone ring structure.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Cyclobutanone derivatives are versatile synthetic intermediates.
- Nickel-catalyzed reactions offer unique pathways for C-C bond formation.
- Intramolecular reactions are crucial for constructing complex cyclic systems.
Purpose of the Study:
- To develop a novel synthetic route to benzobicyclo[2.2.2]octenones.
- To investigate the utility of nickel(0) catalysis in cyclobutanone transformations.
- To explore the mechanism of vinyl group insertion into cyclobutanone skeletons.
Main Methods:
- Reaction of 3-styrylcyclobutanones with a nickel(0) catalyst.
- Analysis of reaction products using spectroscopic techniques (e.g., NMR, MS).
- Mechanistic studies to elucidate the reaction pathway.
Main Results:
- Efficient conversion of 3-styrylcyclobutanones to benzobicyclo[2.2.2]octenones was achieved.
- The reaction proceeded via an intramolecular insertion of the vinyl moiety.
- The nickel(0) catalyst was crucial for facilitating this transformation.
Conclusions:
- A new method for synthesizing benzobicyclo[2.2.2]octenones has been established.
- Nickel(0) catalysis enables a unique intramolecular vinyl insertion into cyclobutanones.
- This methodology expands the synthetic toolkit for accessing complex polycyclic structures.
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