Practical Synthesis of Terminal Vinyl Fluorides.

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Fluorine Chemistry

Background:

• Synthesizing di- and trisubstituted vinyl fluorides with high isomeric purity is challenging.
• Existing methods often require difficult isomer separation, hindering practical application.

Purpose of the Study:

• To develop a practical and efficient method for accessing highly isomeric pure di- and trisubstituted vinyl fluorides.
• To provide a scalable synthetic route applicable to diverse substrates.

Main Methods:

• Selective Horner-Wadsworth-Emmons olefination followed by hydrolysis to yield crystalline 2-fluoroacrylic acids.
• Stereoretentive decarboxylation catalyzed by silver to produce the target vinyl fluorides.

Main Results:

• Achieved high (>98%) E-isomeric purity of 2-fluoroacrylic acids.
• Synthesized diverse di- and trisubstituted vinyl fluorides with high isomeric purity.
• Eliminated the need for tedious chromatographic separation of isomers.

Conclusions:

• The developed method offers a practical and efficient route to high-purity vinyl fluorides.
• The synthetic sequence is versatile and applicable to various aldehydes and ketones.
• The method was successfully applied to the synthesis of biologically active compounds, including antibacterial and anti-inflammatory agents.