1,3-Diphenyldisiloxane Enables Additive-Free Redox Recycling Reactions and Catalysis with Triphenylphosphine

Joseph A. Buonomo, Malcolm S. Cole, Carter G. Eiden, Courtney C. Aldrich

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The recently reported chemoselective reduction of phosphine oxides with 1,3-diphenyldisiloxane (DPDS) has opened up the possibility of additive-free phosphine oxide reductions in catalytic systems. Herein we disclose the use of this new reducing agent as an enabler of phosphorus redox recycling in Wittig, Staudinger, and alcohol substitution reactions. DPDS was successfully utilized in ambient-temperature additive-free redox recycling variants of the Wittig olefination, Appel halogenation, and Staudinger reduction. Triphenylphosphine-promoted catalytic recycling reactions were also facilitated by DPDS. Additive-free triphenylphosphine-promoted catalytic Staudinger reductions could even be performed at ambient temperature due to the rapid nature of phosphinimine reduction, for which we characterized kinetic and thermodynamic parameters. These results demonstrate the utility of DPDS as an excellent reducing agent for the development of phosphorus redox recycling reactions.

Original languageEnglish (US)
Pages (from-to)3583-3594
Number of pages12
JournalSynthesis (Germany)
Volume52
Issue number23
DOIs
StatePublished - Dec 1 2020

Keywords

  • azide reduction
  • disiloxanes
  • halogenation
  • olefination
  • organocatalysis
  • phosphines

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