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

Research output: Contribution to journalArticle

192 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 languageEnglish
Pages (from-to)11310-11311
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number32
DOIs
Publication statusPublished - 2009 Aug 19

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Halogenation
Electrochemical oxidation
Palladium
Hydrogen
Aromatic compounds
Oxidants
Organic solvents
Electrolytes
Catalyst activity
Salts
Ligands
Ions
Catalysts
Substrates

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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 journalArticle

Kakiuchi, Fumitoshi ; Kochi, Takuya ; Mutsutani, Hitoshi ; Kobayashi, Noboru ; Urano, Seiya ; Sato, Mitsuo ; Nishiyama, Shigeru ; Tanabe, Takamasa. / Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 32. pp. 11310-11311.
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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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