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

Marie Kobylarski # 1 Liam Donnelly 1 Jean-Claude Berthet 1 Thibault Cantat 1 
1 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
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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https://hal-cea.archives-ouvertes.fr/cea-03683047
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Submitted on : Tuesday, May 31, 2022 - 2:33:40 PM
Last modification on : Thursday, June 2, 2022 - 3:42:44 AM

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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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