Aerobic oxidation of 5-hydroxymethylfurfural to 5-hydroxymethyl-2-furancarboxylic acid and its derivatives by heterogeneous NHC-catalysis

Arianna Brandolese, Daniele Ragno, Graziano Di Carmine, Tatiana Bernardi, Olga Bortolini, Pier Paolo Giovannini, Omar Ginoble Pandoli, Alessandra Altomare, Alessandro Massi*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

The application of the oxidative system composed of a heterogeneous triazolium pre-catalyst, iron(ii) phthalocyanine and air is described for the selective conversion of 5-hydroxymethylfurfural (HMF) into the added-value 5-hydroxymethyl-2-furancarboxylic acid (HMFCA). The disclosed one-pot two-step procedure involved sequential oxidative esterifications of HMF to afford a polyester oligomer having hydroxyl and carboxyl terminal groups (M w = 389-1258), which in turn was hydrolyzed by a supported base (Ambersep 900 OH) to yield HMFCA in 87% overall yield. The same strategy was adopted for the effective synthesis of ester and amide derivatives of HMFCA by nucleophilic depolymerization of the oligomeric intermediate with methanol and butylamine, respectively. The utilization of the disclosed oxidative system for the direct conversion of HMF and furfural into their corresponding ester, amide, and thioester derivatives is also reported.

Original languageEnglish
Pages (from-to)8955-8964
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number46
DOIs
Publication statusPublished - 2018

Bibliographical note

Funding Information:
We gratefully acknowledge the University of Ferrara (fondi FAR) for financial support. Thanks are also given to Paolo Formaglio for NMR experiments.

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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