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Palladium-Catalyzed Aromatic C−H Halogenation with Hydrogen Halides by Means of Electrochemical Oxidation

2009; American Chemical Society; Volume: 131; Issue: 32 Linguagem: Inglês

10.1021/ja9049228

1943-2984

Fumitoshi Kakiuchi, Takuya Kochi, Hitoshi Mutsutani, Noboru Kobayashi, Seiya Urano, Mitsuo Sato, Shigeru Nishiyama, Takamasa Tanabe,

Oxidative Organic Chemistry Reactions

A new strategy for catalytic functionalization of C-H bonds by means of electrochemical oxidation is described. Combination of palladium-catalyzed aromatic C-H bond cleavage and halogenation with electrochemically generated halonium ions enables highly efficient, selective halogenations of aromatic compounds in a green-sustainable manner. The required reagents for this reaction are an arene and an aqueous hydrogen halide as substrates, a palladium salt as a catalyst, and an organic solvent. No further additives such as electrolytes, oxidants, or ligands are necessary to achieve effective catalytic activity. Several remarkable advantages of the use of the electrochemical method are also described.