Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation

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

doi:10.1021/ja9049228

Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation

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

Department of Chemistry

Research output: Contribution to journal › Article

199 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	11310-11311
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	131
Issue number	32
DOIs	https://doi.org/10.1021/ja9049228
Publication status	Published - 2009 Aug 19

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ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Cite this

Kakiuchi, F., Kochi, T., Mutsutani, H., Kobayashi, N., Urano, S., Sato, M., Nishiyama, S., & Tanabe, T. (2009). Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation. Journal of the American Chemical Society, 131(32), 11310-11311. https://doi.org/10.1021/ja9049228

Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation. / Kakiuchi, Fumitoshi ; Kochi, Takuya; Mutsutani, Hitoshi; Kobayashi, Noboru; Urano, Seiya; Sato, Mitsuo; Nishiyama, Shigeru; Tanabe, Takamasa.

In: Journal of the American Chemical Society, Vol. 131, No. 32, 19.08.2009, p. 11310-11311.

Research output: Contribution to journal › Article

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AB - (Chemical Equation Presented) 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.

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10.1021/ja9049228