Catalyst/Metal-free Synthesis of Aryl Compounds

Background

Commercial‑scale production of agricultural chemicals, dyes, and other functionalized organics requires economic projection that can absorb the expenses of variable‑cost reagents, costly solvents and catalysts, and variable energy prices required to run the unit operations. In commodity markets especially this create little margin for error in these projections and leaves little room to increase profits without increasing selling price; therefore, a new chemistry regime is needed to create new synthesis pathways which enable manufacturers to reduce input and processing costs.

Technology Overview

The hypervalent iodine moiety of diaryliodonium salts is unique among non-metals for its ability to mediate the formation of new bonds by a reductive elimination-like pathway. shows an exemplary list of compounds that have been synthesized with high efficiency and reaction selectivity. Efficient one-pot protocols to access diaryliodonium salts from aryl iodides continue to be developed at PSU due to growing interest in metal-free arylation reactions of these reagents; however, this chemistry is new and exploration has not yet been driven explicitly by industry needs. shows the initial scope of compounds that have been synthesized using a one‑pot method without HPLC or ligand‑based separations, and illustrates further examples of unsymmetrical aryl(2,4,6-trimethoxyphenyl)iodonium salts as synthetically‑useful, metal-free arylation reagents.

Benefits

• Removes the need for HPLC separations at the late stages of complex reactions, reducing capital cost of production equipment and long‑term savings by reducing or eliminating solvent‑based extraction methods that would otherwise be required.
• Eliminates the need for transition metal‑based catalysts for reactions that are nucleophile‑based.

Applications

• Agrochemicals
• Polymers
• Pharmaceuticals
• Dyes
• Other commodity chemical reactions (especially those that require metal‑catalyzed nucleophile addition steps)

Opportunity

PSU would like to collaborate with industry partners that can inform development of reactions targeted toward specific and pressing market needs. The underlying chemistry is NOT patented and has been published; however, the research team is looking for partners that would like to explore specific reaction pathways with the potential to develop protectable IP around end products.