Synthesis of N‐Substituted Pyrrole‐2,5‐dicarboxylic Acids from Pyrroles

Author:

Jeshua Friedrichs Jan‐Simon1ORCID,Schmermund Luca1ORCID,Urmann Corinna23ORCID,Sieber Volker1456ORCID

Affiliation:

1. Chair of Chemistry of Biogenic Resources Campus Straubing for Biotechnology and Sustainability Technical University of Munich Schulgasse 16 94315 Straubing Germany

2. Organic-analytical Chemistry Weihenstephan-Triesdorf University of Applied Sciences Schulgasse 16 94315 Straubing Germany

3. TUM Campus Straubing for Biotechnology and Sustainability Technical University of Munich Schulgasse 16 94315 Straubing Germany

4. Catalytic Research Center Technical University of Munich Ernst-Otto-Fischer-Straße 1 85748 Garching Germany

5. SynBiofoundry @TUM Technical University of Munich Schulgasse 22 94315 Straubing Germany

6. School of Chemistry and Molecular Biosciences The University of Queensland 68 Copper Road St. Lucia 4072 Australia

Abstract

AbstractPyrrole‐2,5‐dicarboxylic acid (PDCA) is a heterocyclic aromatic dicarboxylic acid that may emerge as a new monomer for polyester production. Compared to its structurally related and bio‐based furan‐2,5‐dicarboxylic acid (FDCA) that is already used for the production of polyethylene furanoate (PEF), PDCA shows excellent potential as its nitrogen can be targeted for further derivatization, thus enabling tuning of the properties of a PDCA containing polymer. In light of this, we recognized the need to explore efficient synthetic approaches for producing PDCAs in high yields. Here, we report a five‐step synthesis route for N‐substituted PDCAs starting from pyrrole, with total yields up to 42 %. The synthetic approach allowed the introduction of several different functional moieties to the pyrrole nitrogen, such as aliphatic saturated and unsaturated side‐chains, as well as benzylic groups.

Publisher

Wiley

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