EDA Complex-Enabled Annulation to Access CF2-Containing Tetralones and Quinazolinones Using Persulfates as Electron
Shu-Peng Zhang1, Da-Wei Guo1, Mei-Ling Yang1
1Guangling College and School of Plant Protection, Yangzhou University, Yangzhou 225009, P. R. China.
The Journal of Organic Chemistry
|July 25, 2024
Summary
This study introduces a new, metal-free method using electron donor-acceptor (EDA) complexes for synthesizing fluorine-containing compounds. The reaction efficiently creates valuable tetralones and quinazolinones from simple starting materials under mild conditions.
Area of Science:
- Organic Chemistry
- Fluorine Chemistry
- Photochemistry
Background:
- Synthesizing complex fluorine-containing molecules often requires harsh conditions or expensive catalysts.
- Developing efficient and sustainable methods for incorporating fluorine into organic structures is crucial for pharmaceuticals and materials science.
Purpose of the Study:
- To develop a novel photocatalyst-free method for synthesizing fluorine-containing tetralones and quinazolinones.
- To utilize electron donor-acceptor (EDA) complex-enabled radical cascade cyclization for this purpose.
Main Methods:
- The reaction employs persulfates as electron donors and bromodifluoroacetamides as electron acceptors to generate an EDA complex.
- This EDA complex facilitates a radical cascade cyclization of inactive alkenes.
Main Results:
- Successfully synthesized diverse fluorine-containing tetralones and quinazolinones.
- Demonstrated a photocatalyst-free, metal-free transformation.
- Achieved excellent functional group tolerance under mild reaction conditions.
Conclusions:
- The developed EDA complex-enabled radical cascade cyclization is an efficient and versatile method for synthesizing fluorinated heterocycles.
- This approach offers a sustainable and practical alternative to existing synthetic strategies.
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