Electroreduction of tetra-coordinate phosphonium derivatives; One-pot transformation of triphenylphosphine oxide into triphenylphosphine

Manabu Kuroboshi, Tomotake Yano, Shogo Kamenoue, Hiromu Kawakubo, Hideo Tanaka

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Electroreduction of triphenylphosphine dichloride in acetonitrile was performed successfully in an undivided cell fitted with an aluminium sacrificial anode and a platinum cathode, wherein Al3+, which was electrogenerated at the anode would react as a Lewis acid with triphenylphosphine dichloride to afford tetra-coordinate chlorotriphenylphosphonium species and subsequent two-electron reduction at the cathode would give triphenylphosphine. One-pot transformation of triphenylphosphine oxide to triphenylphosphine was achieved successfully by the treatment of triphenylphosphine oxide with oxalyl chloride and subsequent electroreduction. In a similar manner, some tetra-coordinate triphenylphosphonium species derived from triphenylphosphine oxide were reduced electrochemically to triphenylphosphine in moderate yields.

Original languageEnglish
Pages (from-to)5825-5831
Number of pages7
JournalTetrahedron
Volume67
Issue number32
DOIs
Publication statusPublished - Aug 12 2011

Fingerprint

Derivatives
Electrodes
Anodes
Cathodes
Lewis Acids
Platinum
Aluminum
triphenylphosphine
triphenylphosphine oxide
Electrons

Keywords

  • Electroreduction
  • Tetra-coordinate phosphonium
  • Triphenylphosphine
  • Triphenylphosphine dichloride
  • Triphenylphosphine oxide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Electroreduction of tetra-coordinate phosphonium derivatives; One-pot transformation of triphenylphosphine oxide into triphenylphosphine. / Kuroboshi, Manabu; Yano, Tomotake; Kamenoue, Shogo; Kawakubo, Hiromu; Tanaka, Hideo.

In: Tetrahedron, Vol. 67, No. 32, 12.08.2011, p. 5825-5831.

Research output: Contribution to journalArticle

Kuroboshi, Manabu ; Yano, Tomotake ; Kamenoue, Shogo ; Kawakubo, Hiromu ; Tanaka, Hideo. / Electroreduction of tetra-coordinate phosphonium derivatives; One-pot transformation of triphenylphosphine oxide into triphenylphosphine. In: Tetrahedron. 2011 ; Vol. 67, No. 32. pp. 5825-5831.
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