Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a Practical Auxiliary: A Weak-Coordination Approach


  • We gratefully acknowledge TSRI and the US NSF (NSF CHE-1011898), Amgen, and Eli Lilly for financial support. We thank the A. P. Sloan Foundation for a fellowship (J.-Q.Y.), the Agency for Science, Technology and Research (A*STAR) Singapore for a predoctoral fellowship (K.C.), and Bristol Myers Squibb for a predoctoral fellowship (M.W.). TSRI Manuscript no. 21264.


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Finally, a choice! A highly selective palladium(II)-catalyzed ortho-monofluorination reaction has been achieved for the first time through a weak coordination (see scheme; Ar=2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl). Simple modification of this protocol allows for a choice between mono- and difluorination. The mono- and difluorinated benzoic acid derivatives are valuable in the pharmaceutical and agrochemical industries.