4.7 Article

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diols via pressure hydrogenation of potentially biobased platform molecules using Knolker-type catalysts

Journal

DALTON TRANSACTIONS
Volume 50, Issue 29, Pages 10102-10112

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1dt01252e

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Funding

  1. European Regional Development Fund (ERDF) within the framework of OP-Zuid
  2. Dutch provinces of Noord-Brabant and Limburg
  3. Dutch Ministry of Economy

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This study presents the hydrogenative conversion of biobased platform molecules to their corresponding diols using a pre-activated Knolker-type iron catalyst. The catalyst demonstrates high selectivity for ketone reduction without inducing dehydration, and the cis-trans ratio of products can be substantially affected by different ligand substituents. Additionally, the catalytic system shows decent compatibility with various structurally related substrates.
The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Knolker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, the cis-trans ratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

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