Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides
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Buchwald_Formation of ArF.pdf
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Author(s)
Watson, Donald A.
Su, Mingjuan
Teverovskiy, Georgiy
Zhang, Yong
Garcia-Fortanet, Jorge
Kinzel, Tom
Buchwald, Stephen Leffler
Date Issued
August 2009
Journal
Science
Publisher
American Association for the Advancement of Science (AAAS)
Citation
Watson, D. A., M. Su, G. Teverovskiy, Y. Zhang, J. Garcia-Fortanet, T. Kinzel, and S. L. Buchwald. “Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides.” Science 325, no. 5948 (September 24, 2009): 1661-1664.
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Author's final manuscript
Abstract
Despite increasing pharmaceutical importance, fluorinated aromatic organic molecules remain difficult to synthesize. Present methods require either harsh reaction conditions or highly specialized reagents, making the preparation of complex fluoroarenes challenging. Thus, the development of general methods for their preparation that overcome the limitations of those techniques currently in use is of great interest. We have prepared [LPd(II)Ar(F)] complexes, where L is a biaryl monophosphine ligand and Ar is an aryl group, and identified conditions under which reductive elimination occurs to form an Ar-F bond. On the basis of these results, we have developed a catalytic process that converts aryl bromides and aryl triflates into the corresponding fluorinated arenes by using simple fluoride salts. We expect this method to allow the introduction of fluorine atoms into advanced, highly functionalized intermediates.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1126/science.1178239
