Cross Coupling of Phenolic Derivatives

UC Case No. 2009-085

SUMMARY:

Investigators at UCLA have identified a new reaction that enables carbon-carbon bonds and carbon-heteroatom bonds to be introduced into organic molecules. The reaction is cost-effective and highly efficient.

BACKGROUND:

Synthesis of organic molecules plays a vital role in modern society: carbon-carbon and carbon heteroatom bonds are encountered in natural products, materials, drug substances and agrochemicals. There are currently methods in place for coupling phenol groups to carbon atoms, but these reactions require expensive materials and are often not efficient. Practical methods that allow for the cross coupling of phenol derivatives to carbon atoms are therefore extremely interesting, especially given their prevalence in the pharmaceutical industry.

INNOVATION:

Researchers at UCLA have identified reactions that utilize unconventional phenol derivatives as cross-coupling partners, resulting in an extremely cost-effective method for introducing C-X or C-C bonds into organic molecules and drug substances.

POTENTIAL APPLICATIONS:

• Process chemists in pharmaceutical industry
• Synthesis of drugs or other materials

ADVANTAGES:

• Reagents are easy to prepare
• Reagents are very cost-effective
• Reagents are stable to a variety of reaction conditions
• Reagents are able to direct installation of other functional groups on an aromatic ring

RELATED MATERIALS:

• Quasdorf, Tian and Garg. Cross-coupling Reactions of Aryl Pivalates with Boronic Acids. J. Am. Chem. Soc. (2008)

STATE OF DEVELOPMENT:

The invention has been tested and is confirmed to work. Researchers are currently exploring the scope of substrates that can be used in the reaction.