Investigation of trifluoromethanesulfonate as a leaving group in the fluorination of aromatic compounds

ORGN 527

Brian H. Keogh Jr., bhkeogh@yahoo.com, Department of Chemistry and Biochemistry, University of Northern Colorado, Campus Box 98, Greeley, CO 80639 and Richard M. Hyslop, School of Chemistry, Earth Sciences, and Physics, University of Northern Colorado, Campus Box 98, Greeley, CO 80639.
Fluorinated aromatics are an important class of compounds in a variety of industries, especially pharmaceuticals as a number of drugs contain a fluorinated aromatic substituent. While there have been some advances in non-aromatic fluorination methodologies in the past decade, the Balz-Schiemann reaction, a method developed in the early 1900's, is still the standard procedure used to prepare fluorinated aromatics. The development of a new method to fluorinate aromatic compounds is desirable, as this may allow for the preparation of new molecules. This project was undertaken to investigate the use of trifluoromethanesulfonate (triflate) as a leaving group for aromatic fluorination. The method involves activating phenols and other aromatic alcohols with trifluoromethanesulfonyl chloride (triflic chloride), then displacing the triflate with a suitable fluoride ion source. Preliminary data indicates the successful triflation of phenol in moderate yield, with further results to be presented.
 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006