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. 2018 Sep 7;8(55):31496-31501.
doi: 10.1039/c8ra05983g. eCollection 2018 Sep 5.

The synthesis of HMF-based α-amino phosphonates via one-pot Kabachnik-Fields reaction

Weigang Fan  1 , Yves Queneau  1 , Florence Popowycz  1
Affiliations

The synthesis of HMF-based α-amino phosphonates via one-pot Kabachnik-Fields reaction

Weigang Fan et al. RSC Adv. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. The Kabachnik–Fields reaction of HMF and different amines.a,b aThe reaction was carried out with HMF (1 mmol), amine (1 mmol), diethyl phosphite (1.5 mmol) with I2 (5 mol%) in 2-MeTHF (2 mL), stirred at 25 °C for indicated time. bIsolated yield. cAt 50 °C.
Scheme 2
Scheme 2. The Kabachnik–Fields reaction of HMF and commercially available phosphites.
Scheme 3
Scheme 3. The double Kabachnik–Fields reaction.
Scheme 4
Scheme 4. The derivatizations on hydroxyl group.
Scheme 5
Scheme 5. Control experiments.
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