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Catalytic Cascade for Biomass Valorisation: Coupled Hydrogen Transfer Initiated Dehydration (Htid) and Self-Aldol Condensation (Sac) for the Synthesis of 2-Methyl-Pent-2-Enal from 1,3-Propanediol
Version 1
: Received: 18 June 2024 / Approved: 19 June 2024 / Online: 19 June 2024 (05:53:25 CEST)
How to cite:
Ma, Y.; Wang, Y.-M.; Lorenzini, F.; Marr, A. C. Catalytic Cascade for Biomass Valorisation: Coupled Hydrogen Transfer Initiated Dehydration (Htid) and Self-Aldol Condensation (Sac) for the Synthesis of 2-Methyl-Pent-2-Enal from 1,3-Propanediol. Preprints2024, 2024061305. https://doi.org/10.20944/preprints202406.1305.v1
Ma, Y.; Wang, Y.-M.; Lorenzini, F.; Marr, A. C. Catalytic Cascade for Biomass Valorisation: Coupled Hydrogen Transfer Initiated Dehydration (Htid) and Self-Aldol Condensation (Sac) for the Synthesis of 2-Methyl-Pent-2-Enal from 1,3-Propanediol. Preprints 2024, 2024061305. https://doi.org/10.20944/preprints202406.1305.v1
Ma, Y.; Wang, Y.-M.; Lorenzini, F.; Marr, A. C. Catalytic Cascade for Biomass Valorisation: Coupled Hydrogen Transfer Initiated Dehydration (Htid) and Self-Aldol Condensation (Sac) for the Synthesis of 2-Methyl-Pent-2-Enal from 1,3-Propanediol. Preprints2024, 2024061305. https://doi.org/10.20944/preprints202406.1305.v1
APA Style
Ma, Y., Wang, Y. M., Lorenzini, F., & Marr, A. C. (2024). Catalytic Cascade for Biomass Valorisation: Coupled Hydrogen Transfer Initiated Dehydration (Htid) and Self-Aldol Condensation (Sac) for the Synthesis of 2-Methyl-Pent-2-Enal from 1,3-Propanediol. Preprints. https://doi.org/10.20944/preprints202406.1305.v1
Chicago/Turabian Style
Ma, Y., Fabio Lorenzini and Andrew Craig Marr. 2024 "Catalytic Cascade for Biomass Valorisation: Coupled Hydrogen Transfer Initiated Dehydration (Htid) and Self-Aldol Condensation (Sac) for the Synthesis of 2-Methyl-Pent-2-Enal from 1,3-Propanediol" Preprints. https://doi.org/10.20944/preprints202406.1305.v1
Abstract
A one-pot, one-step protocol combining hydrogen transfer initiated dehydration (HTID) of 1,3-propanediol (1,3-PDO), catalysed by [Cp*IrCl2(NHC)] (Cp* = pentamethylcyclopentadienyl; NHC = carbene ligand) complexes (1-5H and 1-3F), and self-aldol condensation (SAC) of propanal (2), allowed selective production of aldehyde 2-methyl-pent-2-enal (3), in ionic liquids with high substrate conversion. The Ir(III) pre-catalysts, and the ionic liquids, were recyclable. 3 could also be selectively produced in the presence of water, and in neat 1,3-PDO. The efficient, selective delivery of a value-added chemical from 1,3-PDO, a major product of many whole cell bacterial fermentation processes, shows that the combination of chemo-catalytic processing of the chemical platform via Cp*IrCl2(NHC) - catalysed HTID / SAC with bio-catalysis has the potential to allow direct valorisation of the bio-renewable feedstocks, such as waste glycerol and sugars, into valuable chemicals.
Chemistry and Materials Science, Organic Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
