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PdII-Catalyzed Monoselective ortho Halogenation of C[BOND]H Bonds Assisted by Counter Cations: A Complementary Method to Directed ortho Lithiation


  • We thank The Scripps Research Institute, Brandeis University, and the U.S. National Science Foundation (NSF CHE-0615716) for financial support, and the Camille and Henry Dreyfus Foundation for a New Faculty Award (J.-Q.Y.).


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When the counterion counts: The yield and selectivity of the title transformation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives (see scheme; monoselectivity: 5:1–18:1). These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds. DMF=N,N-dimethylformamide.