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Polyamide monomers via carbonate-promoted C–H carboxylation of furfurylamine

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Abstract

Inedible biomass (lignocellulose) is a largely untapped resource for polymer production because it is synthetically challenging to convert to useful monomers. Here we describe streamlined syntheses of two polyamide monomers from furfurylamine, one of very few chemicals made industrially from lignocellulose. Using carbonate-promoted C–H carboxylation, furfurylamine is converted into a furan-containing amino acid and a tetrahydrofuran-containing bicyclic lactam in two and four steps, respectively. Our syntheses avoid the use of protecting groups and multiple stoichiometric organic reagents required by previous, longer routes to these targets. This work facilitates access to furan- and tetrahydrofuran-based polyamides, which are unavailable from petrochemical feedstocks.

Graphical abstract: Polyamide monomers via carbonate-promoted C–H carboxylation of furfurylamine

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Publication details

The article was received on 04 Sep 2019, accepted on 09 Nov 2019 and first published on 11 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC04460D
Chem. Sci., 2020, Advance Article
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Polyamide monomers via carbonate-promoted C–H carboxylation of furfurylamine

    A. W. Lankenau and M. W. Kanan, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC04460D

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