Organic reactions mediated by electrochemically generated ArS+

Kouichi Matsumoto, Seiji Suga, Jun Ichi Yoshida

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Low-temperature electrochemical oxidation of ArSSAr was carried out to generate a pool of "ArS+". Spectroscopic studies ( 1H NMR and CSI-MS) of the resulting solution revealed the accumulation of ArS(ArSSAr)+. The resulting "ArS +" pool reacted with alkenes and alkynes to give diarylthio-substituted products. The "ArS+" pool rapidly reacted with thioacetals to give the corresponding alkoxycarbenium ion pools, which reacted with various carbon nucleophiles (indirect cation pool method). The reaction of the alkoxycarbenium ion pools with stilbene derivatives in the presence of ArSSAr gave thiochroman derivatives. In addition to such stoichiometric reactions, a catalytic amount of "ArS+" serves as an initiator and a chain carrier of some cationic chain reactions involving intramolecular carbon-carbon bond formation. In situ generation of "ArS+" by electrochemical oxidation of ArSSAr with a catalytic amount of electricity in the presence of a substrate is also effective for such cationic chain reactions.

Original languageEnglish
Pages (from-to)2586-2596
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number8
DOIs
Publication statusPublished - Apr 21 2011
Externally publishedYes

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Carbon
Electrochemical oxidation
electrochemical oxidation
Ions
Derivatives
carbon
Stilbenes
Electricity
Nucleophiles
Alkynes
Alkenes
stilbene
Cations
nucleophiles
alkynes
initiators
electricity
Nuclear magnetic resonance
alkenes
ions

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Organic reactions mediated by electrochemically generated ArS+. / Matsumoto, Kouichi; Suga, Seiji; Yoshida, Jun Ichi.

In: Organic and Biomolecular Chemistry, Vol. 9, No. 8, 21.04.2011, p. 2586-2596.

Research output: Contribution to journalArticle

Matsumoto, Kouichi ; Suga, Seiji ; Yoshida, Jun Ichi. / Organic reactions mediated by electrochemically generated ArS+. In: Organic and Biomolecular Chemistry. 2011 ; Vol. 9, No. 8. pp. 2586-2596.
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