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Synfacts 2010(1): 0085-0085  
DOI: 10.1055/s-0029-1218434
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Conversion of Aryl Triflates to Aryl Fluorides

Contributor(s):Paul Knochel, Andreas J. Wagner
D. A. Watson, M. Su, G. Teverovskiy, Y. Zhang, J. García-Fortanet, T. Kinzel, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides
Science  2009,  325:  1661-1664  
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Publication History

Publication Date:
21 December 2009 (online)

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Key words

aryl triflates - aryl fluorides - palladium

Significance

The biaryl phosphine ligand t-BuBrettPhos in combination with [(cinnamyl)PdCl]2 is shown to catalyze the fluorination of aromatic and heteroaromatic triflates using CsF as fluorine source. This reaction proceeds under relatively mild conditions and with high functional group tolerance.

Comment

In a few cases, regioisomeric products are observed, but the overall yields remain high. The success of the reaction crucially depends on the sterically demanding t-BuBrettPhos ligand, since it prevents the formation of dimeric [LPdAr(F)]2, but also promotes reductive elimination of the Ar-F bond due to its large size. This method can be expected to be applicable for the preparation of biologically active aryl fluorides.

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