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Updated: Apr 7, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Gold-catalyzed intramolecular diazo coupling: an efficient macrocyclization towards cyclic olefins
Chenghao Zhu1, Guangyang Xu, Kai Liu
1School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164, P. R. China. jtsun08@gmail.com.
Gold catalysis enables efficient synthesis of cyclic olefins from diazo compounds. Olefin selectivity is tunable by ligand structure and ring size, avoiding harsh reaction conditions.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Gold-catalyzed reactions are powerful tools in organic synthesis.
- Intramolecular coupling of diazo compounds offers a route to cyclic structures.
- Controlling selectivity in olefin synthesis remains a key challenge.
Purpose of the Study:
- To develop a gold-catalyzed intramolecular coupling of diazo compounds for cyclic olefin synthesis.
- To investigate the influence of reaction parameters on yield and selectivity.
- To explore the role of phosphine ligands in gold catalysis.
Main Methods:
- Employing gold catalysts with various phosphine ligands.
- Utilizing intramolecular coupling of diazo compounds.
- Varying reaction conditions, including concentration and temperature.
Main Results:
- Medium and large-ring cyclic olefins were synthesized in moderate to good yields.
- Z/E selectivity of the resulting olefins was found to be highly dependent on the ring size.
- The structure of the phosphine ligand significantly impacted reaction efficiency.
- High dilution conditions were not necessary for successful synthesis.
Conclusions:
- Gold-catalyzed intramolecular coupling provides an effective method for synthesizing cyclic olefins.
- Ring size and phosphine ligand structure are critical factors for controlling olefin selectivity and reaction efficiency.
- The developed method offers a practical approach without requiring high dilution.
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