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Updated: Jul 19, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Oxidative generation of diarylcarbenium ion pools
Masayuki Okajima1, Kazuya Soga, Toshiki Nokami
1Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
Researchers generated diarylcarbenium ion pools via anodic oxidation of diarylmethanes. These reactive intermediates undergo reactions with nucleophiles and reductive homocoupling, enabling further transformations.
Area of Science:
- Organic Chemistry
- Electrochemistry
- Synthetic Methodology
Background:
- Diarylcarbenium ions are important synthetic intermediates.
- Generating and controlling these reactive species is challenging.
Purpose of the Study:
- To develop a novel method for generating diarylcarbenium ion pools.
- To explore the reactivity of these generated pools with various nucleophiles.
- To investigate the reductive homocoupling of diarylcarbenium ions.
Main Methods:
- Anodic oxidation of diarylmethanes to induce C-H bond dissociation.
- Reactions of the generated diarylcarbenium ion pools with nucleophiles (allylsilanes, ketene silyl acetals, aromatic compounds).
- Reductive homocoupling of the diarylcarbenium ion pools.
Main Results:
- Successful generation of diarylcarbenium ion pools using anodic oxidation.
- Demonstrated reactivity of the pools with diverse nucleophiles.
- Achieved reductive homocoupling to form dimers.
- Showcased the dimer as a precursor for diarylcarbenium ion pools via C-C bond dissociation.
Conclusions:
- Anodic oxidation provides an effective route to diarylcarbenium ion pools.
- These pools offer versatile reactivity for synthesizing complex organic molecules.
- The developed methodology allows for both nucleophilic addition and reductive coupling pathways.
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