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Issue 55, 2018, Issue in Progress
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The synthesis of HMF-based α-amino phosphonates via one-pot Kabachnik–Fields reaction

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Abstract

The first use of biomass-derived HMF in the one-pot Kabachnik–Fields reaction is reported here. A wide range of furan-based α-amino phosphonates were prepared in moderate to excellent yields under mild, effective and environmentally-benign conditions: iodine as a non-metal catalyst, biobased 2-MeTHF as the solvent and room or moderate temperature. The hydroxymethyl group of HMF persists in the Kabachnik–Fields products, widening the scope of further modification and derivatization compared to those arising from furfural. Issues involving the diastereoselectivity and double Kabachnik–Fields condensation were also faced.

Graphical abstract: The synthesis of HMF-based α-amino phosphonates via one-pot Kabachnik–Fields reaction

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Publication details

The article was received on 13 Jul 2018, accepted on 27 Jul 2018 and first published on 07 Sep 2018


Article type: Paper
DOI: 10.1039/C8RA05983G
Citation: RSC Adv., 2018,8, 31496-31501
  • Open access: Creative Commons BY-NC license
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    The synthesis of HMF-based α-amino phosphonates via one-pot Kabachnik–Fields reaction

    W. Fan, Y. Queneau and F. Popowycz, RSC Adv., 2018, 8, 31496
    DOI: 10.1039/C8RA05983G

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