Abstract

A rapid method for the reduction of secondary phosphine oxides under mild conditions has been developed, allowing simple isolation of the corresponding free phosphines. The methodology involves the use of pinacol borane (HBpin) to effect the reduction while circumventing the formation of a phosphine borane adduct, as is usually the case with various other commonly used borane reducing agents such as borane tetrahydrofuran complex (BH 3⋅THF) and borane dimethyl sulfide complex (BH 3⋅SMe 2). In addition, this methodology requires only a small excess of reducing agent and therefore compares favourably not just with other borane reductants that do not require a metal co-catalyst, but also with silane and aluminium based reagents. (Figure presented.).

LanguageEnglish
Pages3999-4004
Number of pages6
JournalAdvanced Synthesis & Catalysis
Volume360
Issue number20
Early online date13 Aug 2018
DOIs
StatusE-pub ahead of print - 13 Aug 2018

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phosphine
Phosphines
Boranes
Reducing agents
Oxides
Metals
Reducing Agents
Silanes
Aluminum
Catalysts

Keywords

  • Phosphine oxide
  • pinacol borane
  • reduction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

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title = "Rapid Metal-Free Formation of Free Phosphines from Phosphine Oxides",
abstract = "A rapid method for the reduction of secondary phosphine oxides under mild conditions has been developed, allowing simple isolation of the corresponding free phosphines. The methodology involves the use of pinacol borane (HBpin) to effect the reduction while circumventing the formation of a phosphine borane adduct, as is usually the case with various other commonly used borane reducing agents such as borane tetrahydrofuran complex (BH 3⋅THF) and borane dimethyl sulfide complex (BH 3⋅SMe 2). In addition, this methodology requires only a small excess of reducing agent and therefore compares favourably not just with other borane reductants that do not require a metal co-catalyst, but also with silane and aluminium based reagents. (Figure presented.).",
keywords = "Phosphine oxide, pinacol borane, reduction",
author = "Cei Provis-Evans and Emanuelsson, {Emma Anna Carolina} and Ruth Webster",
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N2 - A rapid method for the reduction of secondary phosphine oxides under mild conditions has been developed, allowing simple isolation of the corresponding free phosphines. The methodology involves the use of pinacol borane (HBpin) to effect the reduction while circumventing the formation of a phosphine borane adduct, as is usually the case with various other commonly used borane reducing agents such as borane tetrahydrofuran complex (BH 3⋅THF) and borane dimethyl sulfide complex (BH 3⋅SMe 2). In addition, this methodology requires only a small excess of reducing agent and therefore compares favourably not just with other borane reductants that do not require a metal co-catalyst, but also with silane and aluminium based reagents. (Figure presented.).

AB - A rapid method for the reduction of secondary phosphine oxides under mild conditions has been developed, allowing simple isolation of the corresponding free phosphines. The methodology involves the use of pinacol borane (HBpin) to effect the reduction while circumventing the formation of a phosphine borane adduct, as is usually the case with various other commonly used borane reducing agents such as borane tetrahydrofuran complex (BH 3⋅THF) and borane dimethyl sulfide complex (BH 3⋅SMe 2). In addition, this methodology requires only a small excess of reducing agent and therefore compares favourably not just with other borane reductants that do not require a metal co-catalyst, but also with silane and aluminium based reagents. (Figure presented.).

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