Related Experiment Video
Updated: Feb 28, 2026
06:46
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
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E/Z Isomerization-Enabled Conversion from Dual-Carbon to Single-Carbon Insertion into an Aromatic System.
Kaiyue Zhuo1, Kaidong Ruan1, Fei-Hu Cui1,2
1College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
JACS Au
|February 27, 2026
Summary
This study introduces a novel method for skeletal modification of aromatic systems using tunable dual-to-single carbon insertion. E/Z isomerization controls alkyne insertion pathways, enabling divergent molecular diversity from identical reagents.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Generating molecular diversity through skeletal modification of aromatic systems is crucial but challenging.
- Existing methods often require diverse strategies and starting materials.
Purpose of the Study:
- To report a tunable dual-to-single carbon insertion method into σ-aromatic metalla-cyclopropenes.
- To establish a new paradigm for temporal control in divergent skeletal editing.
Main Methods:
- Utilizing E/Z isomerization of intermediates to control reaction pathways.
- Employing alkyne insertion into a three-membered ring via [3+2] and [3+1] pathways.
- Modulating reaction selectivity by controlling the timing of alkyne addition.
Main Results:
- Achieved tunable dual-carbon insertion via the E-isomer and single-carbon insertion via the Z-isomer.
- Demonstrated divergent skeletal editing from identical reagents.
- Highlighted the critical role of E/Z isomerization in controlling reaction outcomes.
Conclusions:
- The developed method offers a versatile approach for skeletal modification.
- Temporal control via E/Z isomerization provides a new strategy for synthetic chemistry.
- This work expands the toolkit for creating molecular diversity in aromatic systems.
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