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Friedel-Crafts-Type Electrophilic Radiocyanation of (Hetero)arenes
Casey J McCarthy1,2, Marius Müller2,3,4, Richard Ma1
1Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
Organic Letters
|February 9, 2026
Summary
This study presents a new method for radiocyanation, introducing carbon-11 into molecules using electrophilic aromatic substitution. This approach efficiently synthesizes 11C-aryl nitriles for radiopharmaceuticals.
Area of Science:
- Radiochemistry
- Organic Synthesis
- Medical Imaging
Background:
- Radiocyanation is crucial for incorporating carbon-11 into radiopharmaceuticals.
- Existing methods for radiocyanation can be limited in scope or efficiency.
Purpose of the Study:
- To develop a novel Friedel-Crafts-type and direct C-H radiocyanation method.
- To enable efficient synthesis of 11C-aryl nitrile scaffolds for PET imaging.
Main Methods:
- Electrophilic radiocyanation of (hetero)aryltrimethylgermanes and stannanes.
- Direct C-H radiocyanation of (hetero)arenes.
- In situ oxidation of [11C]CN- to [11C]CNCl for electrophilic aromatic substitution.
Main Results:
- Successful radiocyanation of diverse (hetero)arenes and organometallic precursors.
- Short reaction times and good radiochemical yields achieved.
- Demonstrated utility for accessing 11C-aryl nitrile scaffolds.
Conclusions:
- The developed radiocyanation method is efficient and versatile.
- This approach offers a valuable tool for the synthesis of PET radiotracers.
- Readily available and shelf-stable reagents facilitate practical application.
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