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Cross Coupling of Phenolic Derivatives

Technology Benefits
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
Technology Application
Process chemists in pharmaceutical industry Synthesis of drugs or other materials
Detailed Technology Description
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.
Supplementary Information
Patent Number: US8546607B2
Application Number: US2010889765A
Inventor: Garg, Neil K. | Quasdorf, Kyle W. | Tian, Xia
Priority Date: 25 Sep 2009
Priority Number: US8546607B2
Application Date: 24 Sep 2010
Publication Date: 1 Oct 2013
IPC Current: C07F000502 | C07F000902
US Class: 562007 | 558048 | 558072 | 568017 | 568706
Assignee Applicant: The Regents of the University of California
Title: Cross-coupling of phenolic derivatives
Usefulness: Cross-coupling of phenolic derivatives
Summary: (I) is useful as an intermediate in the synthesis of flurbiprofen (claimed), which is useful as an antiinflammatory drug.
Novelty: Preparing a cross-coupled compound, useful as an intermediate in the synthesis of flurbiprofen, comprises combining e.g. organoboron compound, an aryl alcohol derivative e.g. acylated aryl alcohol compound, and transition metal catalyst
Industry
Chemical/Material
Sub Category
Chemical/Material Application
Application No.
8546607
Others

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.


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.


Related Materials

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


Additional Technologies by these Inventors


Tech ID/UC Case

20427/2009-085-0


Related Cases

2009-085-0

*Abstract

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.

*IP Issue Date
Oct 1, 2013
*Principal Investigator

Name: Neil Garg

Department:


Name: Krastina Petrova

Department:


Name: Kyle Quasdorf

Department:


Name: Michelle Riener

Department:


Name: Xia Tian

Department:

Country/Region
USA

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