Design of redox-mediatory systems for electro-organic synthesis

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Halide ion-promoted desulfo-halogenation was applied successfully to synthesis of 4-chloro-2-azetidinone 1, a potent intermediate for carbapenem synthesis and stereoselective N-glycosylation of 2,3-deoxyglycosides. Bromide ion/N-oxyl compounds (TEMPO) double mediatory systems enabled us to develop several aqueous electrolysis media free from organic solvents, e.g., silica gel or polymer particles/water disperse systems and water-soluble TEMP-Omediated oil-in-water emulsion systems, in which electrooxidation of alcohols was carried out successfully in a simple beaker-type undivided cell under a constant current condition. Notably, the work-up process was very simple and the solid particles (disperse phase) and the aqueous solutions (disperse media) were easily recovered and reused, offering a totally closed system. In Pd(OAc) 2/TEMPO double mediatory systems, electrogeneration of active cationic palladium catalysts was integrated into electrooxidative Wacker-type reaction. In a similar manner, Wacker-type cyclization and homo-coupling of arylboronic acids were successfully achieved.

Original languageEnglish
Pages (from-to)1002-1009
Number of pages8
JournalElectrochemistry
Volume77
Issue number12
Publication statusPublished - Dec 2009

Fingerprint

Water
Halogenation
Ions
Glycosylation
Carbapenems
Electrooxidation
Cyclization
Silica Gel
Palladium
Silica gel
Emulsions
Bromides
Electrolysis
Organic solvents
Polymers
Oils
Alcohols
Catalysts
Acids
Oxidation-Reduction

Keywords

  • Cationic Pd complex
  • Disperse systems
  • Electroorganic synthesis
  • Mediatory system
  • Nanoemulsion
  • Wacker-type reaction

ASJC Scopus subject areas

  • Electrochemistry

Cite this

Design of redox-mediatory systems for electro-organic synthesis. / Tanaka, Hideo; Kuroboshi, Manabu; Mitsudo, Koichi.

In: Electrochemistry, Vol. 77, No. 12, 12.2009, p. 1002-1009.

Research output: Contribution to journalArticle

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