Brønsted Acid Promoted Reduction of Tertiary Phosphine Oxides

Tetiana Krachko, Volodymyr Lyaskovskyy, Martin Lutz, Koop Lammertsma, J. Chris Slootweg

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

Recently, Brønsted acids, such as phosphoric acids, carboxylic acids, and triflic acid, were found to catalyze the reduction of phosphine oxides to the corresponding phosphines. In this study, we fully characterize the HCl, HOTf, and Me2SiHOTf adducts of triphenylphosphine oxide and find that the thermally stable adduct Ph3POH+OTf is efficiently converted into triphenylphosphine at 100 °C in the presence of readily available hydrosiloxanes. Under the same reaction conditions, also Ph3POSiMe2H+OTf selectively affords triphenylphosphine indicating that silylated phosphine oxides are likely intermediates in this process.

Original languageEnglish
Pages (from-to)916-921
Number of pages6
JournalZeitschrift fur Anorganische und Allgemeine Chemie
Volume643
Issue number14
DOIs
Publication statusPublished - 3 Aug 2017

Fingerprint

phosphine
Oxides
Phosphoric Acids
Phosphines
Acids
Carboxylic Acids
triphenylphosphine

Keywords

  • 1,1,3,3-Tetramethyldisiloxane
  • Brønsted acid
  • Poly(methylhydrosiloxane)
  • Reduction
  • Triphenylphosphine oxide

Cite this

Krachko, Tetiana ; Lyaskovskyy, Volodymyr ; Lutz, Martin ; Lammertsma, Koop ; Slootweg, J. Chris. / Brønsted Acid Promoted Reduction of Tertiary Phosphine Oxides. In: Zeitschrift fur Anorganische und Allgemeine Chemie. 2017 ; Vol. 643, No. 14. pp. 916-921.
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abstract = "Recently, Br{\o}nsted acids, such as phosphoric acids, carboxylic acids, and triflic acid, were found to catalyze the reduction of phosphine oxides to the corresponding phosphines. In this study, we fully characterize the HCl, HOTf, and Me2SiHOTf adducts of triphenylphosphine oxide and find that the thermally stable adduct Ph3POH+OTf– is efficiently converted into triphenylphosphine at 100 °C in the presence of readily available hydrosiloxanes. Under the same reaction conditions, also Ph3POSiMe2H+OTf– selectively affords triphenylphosphine indicating that silylated phosphine oxides are likely intermediates in this process.",
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Brønsted Acid Promoted Reduction of Tertiary Phosphine Oxides. / Krachko, Tetiana; Lyaskovskyy, Volodymyr; Lutz, Martin; Lammertsma, Koop; Slootweg, J. Chris.

In: Zeitschrift fur Anorganische und Allgemeine Chemie, Vol. 643, No. 14, 03.08.2017, p. 916-921.

Research output: Contribution to JournalArticleAcademicpeer-review

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T1 - Brønsted Acid Promoted Reduction of Tertiary Phosphine Oxides

AU - Krachko, Tetiana

AU - Lyaskovskyy, Volodymyr

AU - Lutz, Martin

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AB - Recently, Brønsted acids, such as phosphoric acids, carboxylic acids, and triflic acid, were found to catalyze the reduction of phosphine oxides to the corresponding phosphines. In this study, we fully characterize the HCl, HOTf, and Me2SiHOTf adducts of triphenylphosphine oxide and find that the thermally stable adduct Ph3POH+OTf– is efficiently converted into triphenylphosphine at 100 °C in the presence of readily available hydrosiloxanes. Under the same reaction conditions, also Ph3POSiMe2H+OTf– selectively affords triphenylphosphine indicating that silylated phosphine oxides are likely intermediates in this process.

KW - 1,1,3,3-Tetramethyldisiloxane

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KW - Poly(methylhydrosiloxane)

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