Research Article

Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides

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Science  25 Sep 2009:
Vol. 325, Issue 5948, pp. 1661-1664
DOI: 10.1126/science.1178239

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Facile Fluorination

Fluorine atoms have become a useful substituent in pharmaceuticals. However, they remain challenging to introduce synthetically because present methods for carbon-fluorine bond formation require either corrosive conditions or somewhat exotic, and thus expensive, reagents. A sticking point has been the failure of traditional palladium catalysts to couple aryl groups with coordinated fluoride. Watson et al. (p. 1661, published online 13 August; see the Perspective by Gouverneur) show that pairing palladium with a well-designed phosphine ligand produces a versatile catalyst for aryl fluorination using simple fluoride salts. The method tolerates a range of functional groups and should facilitate efficient syntheses of multiple fluoroaromatic targets.


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.

  • * Present address: Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA.

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