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Zirconium-catalysed hydrosilylation of esters and depolymerisation of polyester plastic waste

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Abstract

Schwartz’s reagent, Cp$_2$Zr(H)Cl, has traditionally been used as a stoichiometric reagent for the reduction of unsaturated organic molecules. Recently, methods to use Cp$_2$Zr(H)Cl as a catalyst have been developed through turnover of the Zr–X intermediates, formed upon reaction with an organic substrate, with hydride reagents. Herein, we report the development of a new catalytic pathway for the reduction of esters that uses the bench-stable silane Me(OMe)$_2$SiH (DMMS) as a mild stoichiometric reductant and Cp$_2$Zr(H)Cl as the catalyst. This system exploits the regeneration of Zr–H through the sigma bond metathesis of Zr–O and Si–H to achieve catalyst turnover. These reaction conditions tolerate a range of reducible functional groups (e.g. alkyne, alkene, and nitro) and give high yields of the corresponding alcohol (up to 91% isolated yield). We have also applied this methodology to the reductive depolymerisation of polyesters found in household plastic waste.
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Dates and versions

cea-03683047 , version 1 (31-05-2022)

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Attribution - NonCommercial - NoDerivatives - CC BY 4.0

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Marie Kobylarski #, Liam Donnelly, Jean-Claude Berthet, Thibault Cantat. Zirconium-catalysed hydrosilylation of esters and depolymerisation of polyester plastic waste. 2022. ⟨cea-03683047⟩
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