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Updated: Jan 10, 2026
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
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Nickel-Catalyzed Quinoline Synthesis through Skeletal Editing Strategy Using Calcium Carbide as an Inorganic C2
Zhiqiang Wang1, Wei Chen1, Jinhui Yang2
1College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. China.
Organic Letters
|November 20, 2025
Summary
Calcium carbide enables skeletal editing of heterocyclic compounds, offering a safer alternative to acetylene. This method efficiently synthesizes diverse quinoline derivatives through a one-pot reaction.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Heterocyclic Chemistry
Background:
- Benzo[c]isoxazoles are key precursors in skeletal editing of heterocyclic frameworks.
- Traditional methods often involve hazardous reagents like gaseous acetylene.
Purpose of the Study:
- To develop a novel, efficient, and safer method for synthesizing quinoline derivatives.
- To explore the utility of calcium carbide as a C2 source in organic synthesis.
Main Methods:
- Nickel-catalyzed one-pot three-component reactions.
- Utilizing benzo[c]isoxazoles, organic boronic acids, and calcium carbide.
- Employing molecular surgery for C-O/N-O bond cleavage and C-C/C-N bond formation.
Main Results:
- Efficient synthesis of diverse 3-substituted and 3,4-disubstituted quinolines.
- Demonstrated broad substrate scope and high reaction efficiency.
- Achieved gram-scale applicability with simple workup procedures.
Conclusions:
- Calcium carbide serves as a safe and effective inorganic C2 source, replacing hazardous acetylene.
- This streamlined synthetic strategy enables efficient skeletal editing for quinoline synthesis.
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