Palladium-Catalyzed Conversion of Aryl Triflates to Aryl
Fluorides

doi:10.1055/s-0029-1218434

Synfacts 2010(1): 0085-0085
DOI: 10.1055/s-0029-1218434

Metal-Mediated Synthesis

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

Abstract

Full Text

PDF Download

Key words

aryl triflates - aryl fluorides - palladium

Significance

<P>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.</P>

Comment

<P>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.</P>

Figures