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Updated: May 10, 2026
06:52
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Isomerizing ethenolysis as an efficient strategy for styrene synthesis
Sabrina Baader1, Dominik M Ohlmann, Lukas J Gooßen
1Fachbereich Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Straße 54, 67663 Kaiserslautern, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 19, 2013
Summary
A novel bimetallic catalyst system efficiently converts alkenylarenes into styrenes using ethylene. This process involves cross-metathesis and double bond migration, offering a new synthetic route.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Organic Synthesis
Background:
- Olefin metathesis is a powerful tool for C=C bond formation.
- Developing efficient and selective catalytic systems remains a key challenge.
- Bimetallic systems offer unique reactivity profiles.
Purpose of the Study:
- To develop a bimetallic catalytic system for efficient cross-metathesis.
- To investigate the double bond migration during the reaction.
- To explore the conversion of natural products like eugenol into valuable styrenes.
Main Methods:
- A bimetallic system comprising a palladium complex [{Pd(μ-Br)(tBu3P)}2] and a ruthenium metathesis catalyst was employed.
- The reaction involved cross-metathesis between substituted alkenes and ethylene.
- Alkenylarenes were treated with the catalyst under an ethylene atmosphere.
Main Results:
- The bimetallic system efficiently promoted cross-metathesis between substituted alkenes and ethylene.
- Continuous double bond migration along the alkenyl chain was observed.
- Natural products eugenol, safrol, and estragol were cleanly converted into corresponding styrenes and propylene gas.
Conclusions:
- The developed bimetallic catalyst system is highly effective for synthesizing styrenes from alkenylarenes.
- The reaction proceeds with concurrent double bond migration, offering a unique synthetic pathway.
- This method provides a valuable route for the transformation of natural products.
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