Synthesis of trifluoromethylated alkylboron compounds and incorporation into small molecules and macromolecules

Problem: 

Fluorinated macromolecules are widely utilized in industry, with the most notable example being Teflon, or perfluorotetrafluoroethylene (PTFE). Additionally, methods for incorporating CF3 into small organic molecules are not well developed, but are needed to expand the chemical repertoire for fluorine incorporation into pharmaceuticals, agrochemicals, and materials.

Solution: 

Researchers in the Molander Lab have developed a metal-free synthetic route to incorporate CF3 groups and other fluorinated alkyl chains into small molecules as well as macromolecules using organoboron intermediates to generate newfound, polyfluorinated entities. These organoboron building blocks are bench-stable, with indefinite shelf-life.  The synthetic methods developed allow the introduction of CF3 at sp3-hybridized centers via a novel carbon-carbon bond connection.

Inventor:

Gary A. Molander, Hirschmann-Makineni Professor of Chemistry and Department Chair

Advantages: 

• Low surface tension and coefficient of friction
• High chemical and thermal stability
• More readily soluble than existing fluoropolymers
• Excellent dielectric properties
• Physical properties potentially superior to Teflon / PTFE
• Biodegradability

Applications: 

• Non-stick coatings
• Lubricants
• Surfactants
• Wirings
• Composites
• Bench-stable, trifluoromethylated building blocks for pharmaceutical and agrochemical applications

Stage of Development: 

Proof-of-concept

Intellectual Property: 

UP application (US20160002270) 

Reference Media: 

• Ryu D. et al.  Chem. Eur. J., 2016, 22, p. 120-133.
• Molander G.A. and Ryu D. Angew. Chemie, 2014, 53(51), p. 14181-14185.
• Argintaru O.A. et al.  Angew. Chemie, 2013, 52(51), p. 13656-13660.

Desired Partnerships: 

• License
• Co-development

Docket # Z6435

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