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Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates
Kouichi Matsumoto1, Yuta Hayashi1, Kengo Hamasaki1
1Department of Chemistry, School of Science and Engineering, Kindai University 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
Beilstein Journal of Organic Chemistry
|September 15, 2022
Summary
Researchers discovered electrochemical reduction conditions to synthesize cyclopropane derivatives from alkyl 2-chloroacetates. This environmentally friendly method offers a straightforward procedure for producing these valuable compounds.
Area of Science:
- Organic Electrochemistry
- Synthetic Organic Chemistry
Background:
- Cyclopropane derivatives are important structural motifs in pharmaceuticals and natural products.
- Traditional synthesis of cyclopropanes can involve hazardous reagents or complex procedures.
Purpose of the Study:
- To discover and optimize electrochemical reduction conditions for synthesizing cyclopropane derivatives.
- To investigate the scope, limitations, and scalability of the developed electrochemical method.
Main Methods:
- Electrochemical reduction of alkyl 2-chloroacetates in tetrabutylammonium bromide (Bu4NBr) in N,N-dimethylformamide (DMF).
- Utilized a divided electrochemical cell with platinum (Pt) electrodes.
- Optimized reaction parameters including current density, voltage, and electrolyte concentration.
Main Results:
- Successfully synthesized cyclopropane derivatives via electrochemical reduction.
- Achieved moderate yields for the target cyclopropane compounds.
- Demonstrated the feasibility of scale-up for the electrochemical synthesis.
Conclusions:
- The developed electrochemical method provides an efficient and environmentally friendly route to cyclopropane derivatives.
- The procedure is operationally simple and suitable for broader synthetic applications.
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