Biaryl coupling to generate compounds for pharmaceutical and organic semiconductor applications

Description:

This photoredox catalyst has potential for use in cyclization and intermolecular coupling, which are useful in radical dimerization and polymerisation to produce compounds with complex ring structures and polymers for pharmaceutical, organic semiconductor, and other uses. Yields of 60%-70% have been demonstrated for intra and inter biaryl coupling reactions, and up to 90% for radical cyclizations to cyclized compounds.

Details: Dr. Louis Barriault of the University of Ottawa’s Centre for Catalysis Research and Innovation developed this family of dimeric gold catalysts. The novel structure of these catalysts confers to the catalyst photostability, enabling sustained use and the generation of high yields of product. Our data demonstrates a strong ability to cleave carbon-halogens bonds such as benzyl chlorides and bromides, primary and secondary alkyl bromides, and aryl iodides and bromides. The cleavage of these bonds leads to the formation of new carbon-carbon bonds via radical cyclizations involving a highly efficient photoredox process. The technology has the following advantages:

  • Low cost raw materials used

  • Strong reducing potential of the catalyst enables the cleavage of carbon-halogen bonds (primary alkyl bromides, aryl bromides and aryl iodides or other bonds with higher reduction potential)

  • Environmentally friendly and safe, including use in radical polymerization.

  • Diverse applications as simple reactions using low catalyst loading and a uv light source (sunlight) using regular Pyrex flasks are possible, including direct coupling of aryls, a key building block in pharmaceuticals.

  • Production scale potential in flow chemistry systems.

  • Potential for energy production demonstrated for Dye Sensitized Solar Cells (DSSC).

Patent Information:
For Information, Contact:
Mark Pearson
Technology Transfer Officer
University of Ottawa
mark.pearson@uottawa.ca
Inventors:
Louis Barriault
Guillaume Revol
Terry Mccallum
Mathieu Morin
Keywords: