4.7 Article

The Trityl-Cation Mediated Phosphine Oxides Reduction

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 12, Pages 3035-3043

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100189

Keywords

phosphine; reduction; silane; trityl salts; silyl cation

Funding

  1. Agence Nationale de la recherche [ANR-16-CE07-0018-01]
  2. University of Bordeaux (UBx)
  3. CNRS
  4. Agence Nationale de la Recherche (ANR) [ANR-16-CE07-0018] Funding Source: Agence Nationale de la Recherche (ANR)

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The reduction of phosphine oxides into phosphines using PhSiH3 and Ph3C+[B(C6F5)(4)](-) is highly efficient and yields a broad range of secondary and tertiary alkyl and arylphosphines with various functional groups. The reaction is believed to proceed through the generation of a silyl cation and subsequent reduction by the silane.
Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)(4)](-) as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes.

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