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Rhodaelectrocatalysis for Annulative C-H Activation: Polycyclic Aromatic Hydrocarbons through Versatile Double
Wei-Jun Kong1, Lars H Finger1, João C A Oliveira1
1Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077, Göttingen, Germany.
Angewandte Chemie (International Ed. in English)
|March 6, 2019
Summary
This study introduces a new electrocatalytic method for synthesizing novel polycyclic aromatic hydrocarbons (PAHs). This sustainable approach offers controlled access to diverse, nonplanar PAHs for materials science applications.
Area of Science:
- Materials Science
- Organic Chemistry
- Electrochemistry
Background:
- Structurally diverse polycyclic aromatic hydrocarbons (PAHs) are crucial for advanced materials.
- Controlled synthesis of nonplanar PAHs remains a significant challenge.
Purpose of the Study:
- To develop a novel, sustainable strategy for synthesizing diversely substituted nonplanar PAHs.
- To explore the utility of electrocatalytic C-H transformations in PAH synthesis.
Main Methods:
- Utilized a two-step electrocatalytic process involving C-H activation and annulation.
- Combined rhoda-electrooxidative C-H activation/[2+2+2] alkyne annulation with electrocatalytic cyclodehydrogenation.
- Employed electricity as a sustainable oxidant.
Main Results:
- Achieved modular access to novel nonplanar PAHs with diverse substitutions.
- Fully analyzed the unique molecular topology, photophysical, and electronic properties of synthesized PAHs.
- Demonstrated chemoselective synthesis of iodo-substituted PAHs using metallaelectrocatalysis.
Conclusions:
- The developed electrocatalytic strategy provides efficient and controlled access to valuable nonplanar PAHs.
- This method offers a sustainable alternative for PAH synthesis in materials science.
- The methodology is versatile and applicable for creating functionalized PAHs.
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