Issue 18, 2022

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

Abstract

Schwartz's reagent, Cp2Zr(H)Cl, has traditionally been used as a stoichiometric reagent for the reduction of unsaturated organic molecules. Recently, methods to use Cp2Zr(H)Cl as a catalyst have been developed through turnover of the [Zr]–X intermediates, formed upon reaction with an organic substrate, by 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)2SiH (DMMS) as a mild stoichiometric reductant and Cp2Zr(H)Cl as the catalyst. This system exploits the regeneration of [Zr]–H through the σ-bond metathesis of [Zr]–OR with [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 alcohols (up to 91% isolated yield). This methodology also proved fruitful for the reductive depolymerisation of a variety of polyesters found in household plastic waste.

Graphical abstract: Zirconium-catalysed hydrosilylation of esters and depolymerisation of polyester plastic waste

Supplementary files

Article information

Article type
Communication
Submitted
09 Jūn. 2022
Accepted
26 Aug. 2022
First published
27 Aug. 2022

Green Chem., 2022,24, 6810-6815

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

M. Kobylarski, L. J. Donnelly, J. Berthet and T. Cantat, Green Chem., 2022, 24, 6810 DOI: 10.1039/D2GC02186B

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