Xanthan Sulfuric Acid as an Efficient Biodegradable and Recyclable Catalyst for the One‐Pot Synthesis of α‐Amino Phosphonates

Sun, Guoying; Hou, Jun‐Tao; Dou, Jing-Jie; Lu, Jun; Hou, Yong‐Jie; Xue, Tuo; Zhang, Zhan‐Hui

doi:10.1002/jccs.201000194

Cited by 29 publications

(6 citation statements)

References 50 publications

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“…[28,29] One of the most useful methods for their synthesis which involves the one-pot multi-component condensation of carbonyl compounds, amines, and > P(O)H species, is the Kabachnik-Fields reaction (phospha-mannich) due to their versatility and high yields. [30] But this reaction usually needs various catalysts such as TiO 2 , [31] LiClO 4 , [32] F 3 CO 2 H, [33] [M(OTf)n, M = Li, Mg, Al, Cu, Ce], [34] Amberlite-IR 120, [35] BCl 3 /Al 2 O 3 , [36] phenyl phosphonic acid, [37] TaCl 5 -SiO 2 , [38] xan-than sulfuric acid, [39] and SmI 2 . [40] For this reason, the use of catalysts in organic synthesis is obvious and can't be denied, that affords rapid, homogeneous and at some times more selective reactions.…”

Section: Introductionmentioning

confidence: 99%

A New family of Sulfamidophosphonates Derivatives: Microwave‐Accelerated Multicomponent Synthesis, Characterization and X‐Ray Crystallographic Study**

et al. 2023

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In this present study, we describe a simple, effective and greener one‐pot microwave‐assisted synthesis of novel α‐sulfamidophosphonates 4(a–l), and 5(a, b) that were rationally designed and synthesized following the principle of the superposition of bioactives substructures. This reaction was accomplished by the condensation of various aromatic aldehydes, sulfamide and diethyl phosphite via the Kabachnik‐Fields reaction using ethanol as solvent under catalyst‐free conditions. The corresponding products were obtained with good yields, in short reactions time and no side product was observed. All the newly synthesized compounds were systematically characterized by IR, 1H NMR, 13C NMR and 31P NMR analysis and the structures of the compounds 4 b and 4 c were further analyzed by single crystal X‐ray diffraction.

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Section: Introductionmentioning

confidence: 99%

A New family of Sulfamidophosphonates Derivatives: Microwave‐Accelerated Multicomponent Synthesis, Characterization and X‐Ray Crystallographic Study**

et al. 2023

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“…The phosphite nucleophile and imine electrophile in this reaction created an NÀ CÀ P bond. Previously reported methods of this recognized Kabachnik-Fields reaction involves a variety of catalysts such as HfCl 2 , [23] NbCl 5 , [24] TiO 2 , [25] ceric ammonium nitrate, [26] phosphomolybdic acid, [27] aqueous formic acid, [28] CeCl 3 • 7H 2 O, [29] zinc di(L-prolinate), [30] SbCl 3 /Al 2 O 3 , [31] BF 3 • OEt 2 , [32] gold complex, [33] nano-magnetic sulfated zirconia (Fe 3 O 4 @ZrO 2 /SO 4 2À ), [34] dodecatungstophosphoric acid (DTP/SiO 2 ), [35] dehydroascorbic acid capped magnetite (DHAA-Fe 3 O 4 ), [36] sulfated polyborate, [37] propylphos-phonic anhydride(T3P), [38] xan-than sulfuric acid, [39] oxalic acid, [40] Yttria-zirconia, [41] MgFe 2 O 4, [42] hydrophobic γ-Fe 2 O 3 -Cu-complex, [43] Fe 3 O 4 @SiO 2 -2mimSO 3 H. [44] In addition various solvents like, DMSO, DMF, THF, CH 3 CN, EtOH, CH 3 Cl, MeCN were also used in this type of protocol. The earlier approach for making α-amino phosphonates had a number of challenges such as low yields, hard reaction conditions, prolonged reaction periods, high reaction temperatures, use of toxic catalyst and hazardous solvent.…”

Section: Introductionmentioning

confidence: 99%

Humic Acid: A Green‐Catalyst‐Mediated Solvent‐Free Synthesis of Functionalized Diethyl(Phenyl(phenylamino)methyl)phosphonate

2023

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Humic acid, a high molecular weight, environment friendly biopolymer has been investigated as a catalyst for a straightforward and versatile one‐pot three‐component reaction through famous Kabachnik‐Fields reaction for the diversity‐oriented convergent synthesis of diethyl(phenyl(phenylamino)methyl)phosphonate by using aldehydes, amines and diethyl phosphite under solvent‐free reaction condition. The developed reaction protocol has successfully removed the use of hazardous solvent, toxic reagent, metal catalyst and harsh reaction condition for the synthesis of this important class of compound. The eco‐benign reaction condition, low catalyst loading, easy reaction set‐up, good yield and broad range of functional group tolerance are the key advantages of the reported protocol. Furthermore, the solvent free reaction protocol using humic acid, as a green, non‐toxic, easily available, biodegradable and easily recycled polymeric catalyst convincingly enhances the superiority of this newly developed protocol over the conventional one.

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“…[12,13]. Interestingly, the synthesis of α-aminophosphonates can take a variety of routes, depending on the reactants and catalysts used [14,15]. In particular, most of the catalysts utilized in α-aminophosphonates synthesis are homogeneous catalysts such as lithium perchlorate [16], aluminum chloride [17], and calcium bromide [18].…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Iron-Based MOFs MIL-100(Fe) as Heterogeneous Catalyst in Kabachnick Reaction

et al. 2021

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An effective technique was proposed for the synthesis of novel α-aminophosphonates: a three-component one-pot condensation reaction of aniline, aromatic aldehydes, and triphenyl phosphite in the presence of (MIL-100(Fe)) as a heterogeneous catalyst. Initially, MIL-100(Fe) was synthesized using H3BTC and ferric nitrate at low temperature and atmospheric pressure. Further, MIL-100(Fe) was characterized using various techniques such as XRD, BET surface area, scanning electron microscopy (SEM), Fourier-transform infrared (FT-IR), and thermogravimetric analysis (TGA). Herein, MIL-100(Fe) showed exceptional catalytic performance for the synthesis of α-aminophosphonate and its derivatives compared with conventional solid catalysts, and even homogeneous catalysts. The study demonstrated that MIL-100(Fe) is an ecofriendly and easily recyclable heterogeneous catalyst in Kabachnick reactions for α-aminophosphonate synthesis, with high yield (98%) and turnover frequency (TOF ~ 3.60 min−1) at room temperature and a short reaction time (30 min).

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Xanthan Sulfuric Acid as an Efficient Biodegradable and Recyclable Catalyst for the One‐Pot Synthesis of α‐Amino Phosphonates

Cited by 29 publications

References 50 publications

A New family of Sulfamidophosphonates Derivatives: Microwave‐Accelerated Multicomponent Synthesis, Characterization and X‐Ray Crystallographic Study**

A New family of Sulfamidophosphonates Derivatives: Microwave‐Accelerated Multicomponent Synthesis, Characterization and X‐Ray Crystallographic Study**

Humic Acid: A Green‐Catalyst‐Mediated Solvent‐Free Synthesis of Functionalized Diethyl(Phenyl(phenylamino)methyl)phosphonate

Facile Synthesis of Iron-Based MOFs MIL-100(Fe) as Heterogeneous Catalyst in Kabachnick Reaction

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