En Route to Anthanthrenes through Bottom-up APEX Strategy by peri-C-H Activation
Abhisek Metya1, Supreeta Sen1, Arya Bhattacharyya1
1Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
Organic Letters
|April 10, 2025
Summary
This study presents a new synthetic route for creating polycyclic aromatic hydrocarbons (PAHs) with all-zigzag edges, specifically anthanthrene. This method enables the efficient synthesis of various anthanthrene derivatives, including those relevant to vat orange dyes.
Area of Science:
- Organic Chemistry
- Materials Science
- Catalysis
Background:
- Polycyclic aromatic hydrocarbons (PAHs) with all-zigzag edges are challenging to synthesize.
- Anthanthrene is a key PAH scaffold with potential applications in materials science.
Purpose of the Study:
- To develop a general synthetic strategy for constructing all-zigzag edge PAHs.
- To synthesize anthanthrene and its derivatives with high regioselectivity.
Main Methods:
- Ruthenium(II)-catalyzed APEX reaction at the masked-bay region.
- Density Functional Theory (DFT) studies to support regioselectivity.
Main Results:
- A general synthetic strategy for anthanthrene construction was established.
- The protocol efficiently produced various substituted anthanthrenes with excellent regioselectivity.
- Anthanthrone derivatives, crucial for vat orange dyes, were successfully synthesized.
Conclusions:
- The developed method provides access to elusive all-zigzag edge PAHs.
- This work offers a versatile route for synthesizing functionalized anthanthrenes and anthanthrones.
- The findings have implications for the development of new organic materials and dyes.
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