Modular Photochemical Approach to Access α-CF₃-β-Aryl Carboxylic Acids via an Electron Donor-Acceptor Complex

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Medicinal Chemistry

Background:

• α-CF3-β-aryl carboxylic acids are crucial building blocks for pharmaceuticals.
• Current synthetic methods are limited by harsh conditions, expensive reagents, and poor compatibility.

Purpose of the Study:

• To develop an efficient and accessible synthetic strategy for α-CF3-β-aryl carboxylic acids.
• To overcome the limitations of existing synthetic methodologies.

Main Methods:

• A visible light-mediated arylation of 2-(trifluoromethyl)acrylic acid.
• Utilized thianthrenium salts and diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (HE) to form electron donor-acceptor complexes.
• Operated without photocatalysts or transition metal catalysts.

Main Results:

• Successfully synthesized α-CF3-β-aryl carboxylic acids.
• Demonstrated an efficient reaction pathway.
• Achieved product formation under mild conditions.

Conclusions:

• The developed visible light strategy offers a practical approach for synthesizing α-CF3-β-aryl carboxylic acids.
• This method presents a greener and more economical alternative for pharmaceutical and fluorine chemistry.
• The proposed mechanism involving EDA complex formation provides insight into the reaction pathway.