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Synthesis 2020; 52(23): 3583-3594
DOI: 10.1055/s-0040-1707345
DOI: 10.1055/s-0040-1707345
feature
1,3-Diphenyldisiloxane Enables Additive-Free Redox Recycling Reactions and Catalysis with Triphenylphosphine
Further Information
Publication History
Received: 17 February 2020
Accepted after revision: 30 June 2020
Publication Date:
04 August 2020 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707345.
- Supporting Information
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