Catalyst-free functionalization of aromatic groups in medical compounds

Invention 2018-035

Catalyst-free functionalization of aromatic groups in medical compounds

Catalyst-free method of adding alkyl radicals to molecules of interest with applications in pharmaceutical and material industries.

Market Need

To improve a given molecule’s acidity, lipophilicity, or overall stability, alkyl radicals are often added to aromatic groups. In particular, trifluoromethyl groups have become very important structural additions to pharmaceutical compounds and synthetic materials. The primary approach, however, uses oxidative-reduction (redox) reactions that require expensive catalysts or produce harsh waste byproducts. New methods of trifluoromethylation in a redox-neutral and catalyst-free way are therefore essential.

Technology Summary

To overcome these issues, scientists at McGill University screened compounds activated by light for trifluoromethylation of aromatic group potential. After some modification of a promising compound, a yield of 96% trifluoromethylated product was observed. Since this technology is assisted by light, use of external expensive catalysts and harsh reducing or oxidizing reagents can be avoided. The identified method is therefore a redox-neutral and catalyst-free protocol that is environmentally friendly and has a high yield of trifluoromethylated product. Importantly, these reagents also work on the general alkylation of arenes and can be readily synthesized from cheap starting materials on a large scale.

Advantages

• Light irradiation is used for trifluoromethylation instead of reducing or oxidizing reagents that produce harsh waste byproducts
• Expensive catalysts are no longer need
• Reagents can be readily synthesized from cheap starting materials on a large scale