Electroreduction of triphenylphosphine oxide to triphenylphosphine in the presence of chlorotrimethylsilane

Hiromu Kawakubo, Manabu Kuroboshi, Tomotake Yano, Kazuma Kobayashi, Syogo Kamenoue, Tomomi Akagi, Hideo Tanaka

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18 Citations (Scopus)

Abstract

Electroreduction of triphenylphosphine oxide to triphenylphosphine in an acetonitrile solution of tetrabutylammonium bromide in the presence of chlorotrimethylsilane was performed successfully in an undivided cell fitted with a zinc anode and a platinum cathode under constant current. A plausible mechanism involving, (1) one-electron reduction of triphenylphosphine oxide generating the corresponding anion radical [Ph 3P-O -], (2) subsequent reaction with chlorotrimethylsilane affording the (trimethylsiloxy)triphenylphosphorus radical [Ph 3P-OSiMe 3], and (3) further one-electron reduction followed by P-O bond fission leading to triphenylphosphine is proposed. In a similar manner, electroreduction of some triarylphosphine oxides and alkyldiarylphosphine oxides was executed to give the corresponding phosphine derivatives in good to moderate yields.

Original languageEnglish
Article numberF78211SS
Pages (from-to)4091-4098
Number of pages8
JournalSynthesis
Issue number24
DOIs
Publication statusPublished - 2011

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Keywords

  • electron transfer
  • phosphorus
  • reduction
  • silicon

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

Kawakubo, H., Kuroboshi, M., Yano, T., Kobayashi, K., Kamenoue, S., Akagi, T., & Tanaka, H. (2011). Electroreduction of triphenylphosphine oxide to triphenylphosphine in the presence of chlorotrimethylsilane. Synthesis, (24), 4091-4098. [F78211SS]. https://doi.org/10.1055/s-0031-1289612