Trifluoromethoxylation of Arenes via Intramolecular Trifluoromethoxy Group Migration

Our method of OCF3 compound synthesis will replace older more cumbersome and expensive methods and will unlock the full potential of these compounds

Among the fluorine-containing functional groups, the trifluoromethoxy group (OCF3) is of current interest to the materials, agricultural and pharmaceutical sciences because of its unique structural and electronic properties. Many OCF3 containing biologically active molecules show enhanced effectiveness often coupled with diminished side effects. However, introduction of the OCF3 into organic molecules has remained a challenge and only a few transformations have been developed. The existing approaches require the use of highly toxic, difficult to handle and thermally unstable reagents. In addition, these transformations suffer from narrow substrate scope, poor functional group tolerance, and high costs which hinder the exploration of OCF3.

Dr. Ming-Yu Ngai, Assistant Professor in the Department of Chemistry at Stony Brook, has developed a new protocol which utilizes bench stable reagents, is operationally simple and amenable to gram scale and one-pot synthesis, and shows high functional group tolerance. His novel technology allows an easy trifluoromethoxylation of arenes and heteroarenes via a one-pot two-step sequence of O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives. This new technology will render the OCF3 group as a classical group to consider in all molecular screenings from medicinal chemistry to materials science and provides an easy access to a wide range of synthetically useful ortho-OCF3 aniline derivatives and trifluoromethoxylated compounds.

Easy and cost effective method of producing OCF3 compounds.

Manufacturing OCF3 substituted pharmaceuticals and agrochemicals.

Production and commercialization of new OCF3 bulding blocks.

Molecular screening of OCF3 containing compounds.

Utility application # 15/516610

Proof of concept data is available.

We seek to develop and commercialize, by an exclusive or non-exclusive license agreement and/or sponsored research, with a company active in the area.

Available for License

Triflouromethoxylation, trifluoromethoxy group transfer, Protected anilines, Trifluoromethylation, Intramolecular, N-aryl-hydroxamic acids, Medicinal chemistry, Triflouromethoxide

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