Catalytic C-H Bond Activation

Categories: “Medical and Research Devices“

Reference #: 2012-028

OTC Contact: Sharon E. Pula, Esq. (Directory Information | Send a Message)

Description

Method for transition metal-mediated oxidation of  C-H bonds to form ethers and thioethers.

Applications

• High-throughput combinatorial synthesis
• Compound library generation
• Synthesis of subunits for pharmaceutical and advanced materials

Advantages

• Provides for direct formation of ethers from alcohol thereby minimizing reaction steps, the handling of oxidized intermediates, and environmental impact
• Direct conversion method via oxidant limits the process waste and time consumption associated with functional group manipulation
• Use of copper catalyst is cheaper and more sustainable than using palladium or rhodium as with current methods

Background

Current approaches to ether and thioether generation typically require substrate processing and pre-functionalization to include a labile group (R-X, where R is the substrate and X is the labile group). The labile group is amenable to displacement by another substrate containing a reactive alcohol group (R-OH), the combination ultimately leading to ether generation (R-OR). This approach generates waste, as the preinstalled labile group is discarded along with other reaction products.

In the present invention, Georgetown University researchers have developed an economical approach to ether generation that allows unfunctionalized C-H bonds to be activated such that they may react directly with alcohols groups thus minimizing the reaction steps, the handling of oxidized intermediates and environmental impact. The ubiquity of C-H bonds means this approach can be used to create a vast number of compounds and importantly this approach can also be used for thioether generation.

Stage of Development

Reduced to practice 

Inventors

Timothy Warren
Nicholas Sapiezynski

Patent Status

Issued U.S Patent No. 9,416,080 B2