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Chlorine-free synthesis of phosphinic derivatives by change in the P-function

  • György Keglevich EMAIL logo , Nikoletta Harsági , Betti Szöllősi and László Drahos
Published/Copyright: June 14, 2024
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 13 Issue 1

Abstract

To replace the traditional synthesis of phosphinic amides and phosphinates involving the reaction of phosphinic chlorides with amines and alcohols, respectively, a new chlorine-free approach was aimed at utilizing aminolysis of the phosphinate and alcoholysis of the phosphinic amide. Under microwave conditions, in the presence of [bmim][PF6] catalyst, alkyl diphenylphosphinates were converted to the corresponding phosphinic amides by reaction with primary amines. The reversed transformations involving the alcoholysis of the diphenylphosphinic amides under similar but somewhat more forcing conditions led to phosphinates. The reactivity of the starting phosphinic derivatives, as well as that of the primary amines and alcohols, was evaluated. The work-up included the removal of the excess of the nucleophiles (amine or alcohol) in vacuum followed by flash chromatography. The regenerated nucleophiles could be recycled and reused.

Graphical abstract

Keywords: phosphonates; aminolysis; phosphonic amides; alcoholysis; microwaves; green synthesis; chlorine-free synthesis

1 Introduction

Phosphinic derivatives, a representative group within organophosphorus compounds, are of great importance due to their role as intermediates in syntheses, as biologically active substrates, and as extracting agents [1,2,3,4,5]. The most common preparation of phosphinic amides and phosphinates involves the substitution reaction of phosphinic chlorides by primary or secondary amines, and alcohols or phenols, respectively (Scheme 1) [6,7,8,9]. These syntheses are efficient; however, they cannot be regarded to be “green.” The formation of the hydrochloric acid by-product decreases the atomic efficiency and has to be removed by a base.

Scheme 1 “Classical” way for the synthesis of phosphinic derivatives.
Scheme 1

“Classical” way for the synthesis of phosphinic derivatives.

It is also a possibility that the phosphinic chlorides are prepared from phosphinic acids [6], or formed in situ from secondary phosphine oxides prior to the reaction with amines [10]. P-bromo intermediates were also described [11].

To avoid the use of halogeno-, mainly chloro-intermediates, phosphinic acids should be the choice of reactants. On the one hand, it is possible to use activating agents, such as the T3P® reagent in the amidation or esterification of P-acids using amines and alcohols, respectively [12,13]. A more direct approach is the microwave (MW)-assisted reaction of P-acids with amines [14] and alcohols [15,16]. However, this method can be used only for thermoneutral esterifications with a higher enthalpy of activation [16], and not for endothermic amidations [14]. In the latter case, the conversions remained incomplete under MW irradiation (Scheme 2). The catalytic amount of a suitable ionic liquid promoted the esterifications [15,17].

Scheme 2 “Greener” approaches for the preparation of phosphinates and phosphinic amides.
Scheme 2

“Greener” approaches for the preparation of phosphinates and phosphinic amides.

Regarding the esterification of phosphoric acid derivatives, a green protocol starting from phosphorus pentoxide was developed [18].

The preparation of phosphinates and phosphonates by transesterification of other P-esters is also a sustainable chlorine-free synthesis [19,20]. MW assistance was found useful also in these alcoholyses (Scheme 3) [21,22].

Scheme 3 Modification of phosphinates by alcoholysis.
Scheme 3

Modification of phosphinates by alcoholysis.

Following this line, the aminolysis of phosphinates, and the alcoholysis of phosphinic amides seemed to be relevant. Regarding the first type of transformation, the aminolyses of aryl diphenylphosphinates were investigated mainly from reactivity and mechanistic point of view [23,24,25]. The resulting amides were not isolated, consequently no yields could be reported. To the best of our knowledge, there is only one example for the opposite reaction, for the alcoholyses of phosphinic amides [26]. We aimed at the elaboration of efficient MW-assisted aminolyses and alcoholyses, as shown in Scheme 4.

Scheme 4 New chlorine-free approach for phosphinic amides and phosphinates.
Scheme 4

New chlorine-free approach for phosphinic amides and phosphinates.

Our preliminary results on the interconversion of cyclic phosphinates and phosphinic amides have been published in a short communication [27].

2 Materials and methods

2.1 General

The 31P NMR spectra were taken on a Bruker DRX-500 spectrometer operating at 202.4 MHz. LC–MS measurements were performed with an Agilent 1200 liquid chromatography system coupled with a 6130 quadrupole mass spectrometer equipped with an ESI ion source (Agilent Technologies, Palo Alto, CA, USA). The exact mass (HRMS) measurements were performed using a Waters Q-TOF Premier mass spectrometer in positive electrospray mode. The MW-assisted esterifications were carried out in a CEM Discover MW reactor equipped with a stirrer and a pressure controller using 50–100 W irradiation.

2.2 Procedure for aminolysis of phosphinic esters (1a and 1b) with different amines in the presence of [bmim][PF6]

To 0.68 mmol phosphinate (1a: 0.16 g; 1b: 0.17 g), 10.3 mmol (benzylamine: 1.12 mL; butylamine: 1.01 mL, propylamine: 0.85 mL) and 0.068 mmol (14 µL) of [bmim][PF6] were added. The mixture was irradiated under MW conditions. The crude mixture was filtered through a thin silica gel layer using DCM-MeOH 97:3 as the eluent, and the concentrated filtrate was analyzed by 31P NMR spectroscopy and LC–MS. Column chromatography as above, but using a longer silica-gel layer led to the corresponding phosphinic amides (2a–c) in a pure form (Table 1).

2.3 Procedure for the MW-assisted alcoholysis of phosphinic amides (2a and 2b)

A mixture of 0.90 mmol (2a: 0.28 g, 2b: 0.25 g) phosphinic amide, 13.4 mmol (propanol: 1.02 mL; butanol: 1.24 mL; pentanol: 1.48 mL) of alcohol, and 0.090 mmol (18 µL) of [bmim][PF6] was irradiated in the MW reactor. The crude mixture was filtered through a thin silica gel layer using DCM-MeOH 97:3 as the eluent and analyzed by 31P NMR spectroscopy and LC–MS. Column chromatography as above, but using a longer silica-gel layer, furnished the corresponding phosphinates (1c, 1d, and 1e) in a pure form (Table 1).

Table 1

Identification of the products 1c–e and 2a–c

Compound δ 31P NMR HRMS [M + H]+
Found Literature Found Calculated
Propyl diphenylphosphinate (1c) 31.2 (CDCl3) 31.1 [28] (CDCl3) 261.1039 261.1044
Butyl diphenylphosphinate (1d) 31.9 (CDCl3) 31.1 [28] (CDCl3) 275.1199 275.1201
Pentyl diphenylphosphinate (1e) 31.3 (CDCl3) 31.2 [28] (CDCl3) 289.1354 289.1358
Diphenylphosphinic benzylamide (2a) 23.7 (CDCl3) 23.8 [10] (CDCl3) 308.1201 308.1204
Diphenylphosphinic butylamide (2b) 23.5 (CDCl3) 23.7 [29] (CDCl3) 274.1359 274.1361
Diphenylphosphinic propylamide (2c) 20.0 (CDCl3) 20.6 [30] (CDCl3) 260.1198 260.1204

3 Results and discussion

In the first stage, the MW-assisted, ionic liquid-catalyzed aminolysis of alicyclic phosphinates was investigated. Methyl- and ethyl diphenylphosphinates (1a and 1b) were chosen as the starting materials that can be prepared by the reaction of diphenylphosphinic chloride with methyl alcohol or ethyl alcohol in toluene, in the presence of 1 equivalent of triethylamine. Instead of this traditional method, we chose the “green” approach, the MW-assisted direct esterification of diphenylphosphinic acid with 15 equivalents of the corresponding alcohol in the presence of 10% of butylmethylimidazolium hexafluorophosphate [17].

The first model was the MW-promoted reaction of methyl diphenylphosphinate (1a) with benzylamine used in a 15-fold quantity in a solvolytic-type transformation. After irradiation at 120°C for 20 min, in the lack of [bmim][PF6], the conversion to amide 2a was 54% (Table 2, entry 1), while using 10% of the ionic liquid, the conversion was 90% (Table 2, entry 2). Complete transformation could be achieved at 140°C after a 10 min reaction time (Table 2, entry 3). These conditions could be successfully adopted to the reaction of phosphinate 1a with butylamine and propylamine to furnish amides 2b and 2c in quantitative conversions (Table 2, entries 4 and 5).

Table 2

Aminolysis of alkyl diphenylphosphinates 1a and 1b

Entry R1 Starting material R2 T (°C´) t (min) Conversiona (%) Product Yield (%)
1 Me 1a Bn 120 20 54b 2a —
2 Me 1a Bn 120 20 90 2a —
3 Me 1a Bn 140 10 99 2a 63
4 Me 1a Bu 140 10 100 2b 62
5 Me 1a Pr 140 10 100 2c 66
6 Et 1b Bn 120 30 4 2a —
7 Et 1b Bn 140 120 32 2a
8 Et 1b Bn 160 120 96 2a 64
9 Et 1b Bu 160 150 100 2b 63
10 Et 1b Pr 160 150 89 2c
11 Et 1b Pr 180 120 100 2c 62

aOn the basis of relative 31P NMR intensities. bWithout [bmim][PF6] additive.

Investigating the substitution of ethyl diphenylphosphinate (1b) with benzylamine, after an irradiation at 120°C for 30 min and at 140°C for 2 h, the conversion to amide 2a was as low as 4% and 32%, respectively (Table 2, entry 6 and 7). The best result (96%) was obtained at 160°C/2 h (Table 2, entry 8). The aminolysis with butylamine was complete after an irradiation at 160°C for 2.5 h (Table 2, entry 9). However, the application of this parameter set was not enough for the aminolysis with propylamine (Table 2, entry 10). In this case, there was need for 180°C/2 h (Table 2, entry 11).

The work-up included distillation of the excess of the amine, then flash chromatography of the residue so obtained. From the best experiments (Table 2, entries 3–5 and entries 8, 9, and 11), diphenylphosphinic amides 2a–c were obtained in yields of 62–66% after flash column chromatography.

The significant difference between the reactivity of methyl diphenyl phosphinate 1a and the ethyl counterpart 1b was surprising. Phosphinate 1a is much more reactive. At the same time, there was only a slight difference between the reactivity of the amines applied.

In the next phase of our work, we studied the opposite reaction, the transformation of alicyclic phosphinic amides to phosphinates. Our model involved the alcoholysis of diphenylphosphinic benzylamide (2a) and butylamide (2b) with a 15-fold quantity of propyl alcohol, butyl alcohol and pentyl alcohol under MW conditions. Using pentyl alcohol at 180°C in the lack of ionic liquid catalyst, after an irradiation for 2 h the conversion of amide 2a to phosphinate 1e was as low as 2% (Table 3, entry 1). Repeating the alcoholysis in the presence of 10% of [bmim][PF6], the conversion increased to 77% (Table 3, entry 2). A complete transformation could be achieved after a reaction time of 3 h (Table 3, entry 3). Changing for the alcoholysis of amide 2a with butyl alcohol to provide ester 1d, treatment at 180°C for 3 h was only quantitative in the presence of 20% of [bmim][PF6] (Table 3, entry 4). The other option was to remain with 10% of the catalyst and elevate the temperature to 200°C (Table 3, entry 5). The reaction of benzylamide 2a with propyl alcohol was also performed at 200°C. Complete conversion could be attained after a 4.5 h irradiation using 10% of [bmim][PF6] (Table 3, entry 6), or after a 3.5 h treatment in the presence of 20% of the ionic liquid (Table 3, entry 7). An alternative possibility involved the application of 220°C for 3.5 h and 10% of the catalyst (Table 3, entry 8).

Table 3

Alcoholysis of diphenylphosphinic amides 2a and 2b

Entry R1 Starting material R2 IL (%) T (°C) t (h) Conversiona (%) Product Yield (%)
1 Bn 2a Pent — 180 2 2 1e —
2 Bn 2a Pent 10 180 2 77 1e —
3 Bn 2a Pent 10 180 ∼3 100 1e 78
4 Bn 2a Bu 20 180 3 100 1d —
5 Bn 2a Bu 10 200 3 100 1d 81
6 Bn 2a Pr 10 200 4.5 100 1c 72
7 Bn 2a Pr 20 200 3.5 100 1c 70
8 Bn 2a Pr 10 220 3.5 98 1c 73
9 Bu 2b Pent 10 220 2 100 1e 79
10 Bu 2b Bu 10 220 2 100 1d 82
11 Bu 2b Pr 10 200 4.5 100 1c 74

aOn the basis of relative 31P NMR intensities.

As regards the alcoholysis of diphenylphosphinic butylamide 2b, the completion of the reaction with pentyl alcohol and also with butyl alcohol was complete after irradiation at 220°C for 2 h in the presence of 10% of the catalyst (Table 3, entries 9 and 10). The alcoholysis of amide 2b with propyl alcohol reached a conversion of 100% after treatment at 200°C for 4.5 h in the presence of 10% of the ionic liquid (Table 3, entry 11).

The work-up included distillation of the excess alcohols from the reaction mixtures and then purification of the crude products so obtained by flash chromatography.

It can be seen that the alcoholyses of phosphinic amides 2 were somewhat more reluctant than the aminolyses of phosphinates 1. While the 1 → 2 transformations required a range of 140–180°C, the 2 → 1 conversions took place in the range of 180–220°C. Considering that the amines are more nucleophilic than the alcohols, the theory and practice seem to be in accord. The reactivity order of the alcohols in the alcoholysis of diphenylphosphinic benzylamide 2a is the following:

Besides this, the reactivity of butylamide 2b was significantly lower than that of benzylamide 2a. In the former case, pentyl alcohol and butyl alcohol revealed a similar reactivity.

It is important to note that the excess of the alcohol regenerated on distillation could be re-used in another run.

The phosphinates (1c, 1d, and 1e) and phosphinic amides (2a, 2b, and 2c) prepared are all known compounds described in the literature [28,29,30]. The phosphinic derivatives were identified by 31P NMR chemical shifts and HRMS. The purity was proved by LC–MS.

It is noteworthy that the [bmim][PF6] catalyst significantly improved the conversions. One reason is that the ionic liquid may act as MW absorbers [31]. The other role of the butyl-methyl-imidazolium species is that the proton of its > N═CH–N < moiety interacts with the oxygen atom of the P═O unit [32].

The reactions discussed take place by the nucleophilic addition of the amines or alcohols on the P═O function of the phosphinic ester (3, Y = RO) and the phosphinic amide (3, Y = RNH), respectively, to furnish a pentavalent pentacoordinate intermediate (4) followed by the elimination of alcohol and amine, respectively, to provide the corresponding phosphinic amide (5, Nu = RNH) and phosphinate (5, Nu = RO), respectively (Scheme 5).

Scheme 5 Mechanism for the interconversion of phosphinic derivatives 3 and 5.
Scheme 5

Mechanism for the interconversion of phosphinic derivatives 3 and 5.

It is worth mentioning that after the MW-assisted, ionic liquid-catalyzed interconversion of 1-alkoxy-cyclic phosphine oxides and the 1-amino derivatives [27], the vice-versa transformations could be extended to the case of diphenylphosphinic derivatives. Hence, the novel chlorine-free method seems to be of a more general value; moreover, it is suitable for the transformation of sterically hindered models.

The alcohols and amines were regenerated in ca 80–90% yields on concentrating the reaction mixtures in a vacuum. These nucleophiles were recycled and re-used in newer runs without any limitation.

In summary, a chlorine-free protocol was developed for the synthesis of phosphinic derivatives from each other. Phosphinic amides and phosphinates may be interconverted under MW irradiation in the presence of the 14-fold excess of the corresponding nucleophile (alcohol or amine, respectively) in a solvolytic manner.

4 Conclusions

The traditional preparation of phosphinic esters and amides involves the phosphinoylation of alcohols and amines with phosphinic chlorides. However, this approach is not environmentally friendly due to the application of P-chloride and the liberation of hydrochloric acid, not speaking about the lower atomic efficiency. According to our new procedure, phosphinates may be obtained by the MW-assisted and ionic liquid-catalyzed alcoholysis of phosphinic amides, while phosphinic amides will be the products of the aminolysis of phosphinates performed under similar, but somewhat milder conditions. The excess of the alcohols/amines can be regenerated and re-used in newer runs. The procedures elaborated seem to be of a more general value.

  1. Funding information: This project was supported by the National Research, Development and Innovation Office (K134318).

  2. Author contributions: György Keglevich: writing – original draft, writing – review & editing, project administration, resources; Nikoletta Harsági: methodology, formal analysis writing – experimental; Betti Szöllősi: performing experiments; László Drahos: formal analysis – mass spectrometry.

  3. Conflict of interest: Authors state no conflict of interest.

  4. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

References

[1] Abdou MM. Synopsis of recent synthetic methods and biological applications of phosphinic acid derivatives. Tetrahedron. 2020;76(25):131251. 10.1016/j.tet.2020.131251.Search in Google Scholar

[2] Kiss NZ, Harsági N, Keglevich G. Ionic liquid-promoted synthesis of phosphinates and other derivatives. Phosphorus Sulfur Silicon. 2022;197(5–6):551–3. 10.1080/10426507.2021.2011878.Search in Google Scholar

[3] Vassiliou S, Pagoni A, Weglarz-Tomczak E, Talma M, Tabor W, Grabowiecka A, et al. Phosphinic acid-based enzyme inhibitors. Phosphorus Sulfur Silicon. 2022;197(5–6):451–6. 10.1080/10426507.2021.2011882.Search in Google Scholar

[4] Glowinska A, Trochimczuk AW. Polymer-supported phosphoric, phosphonic and phosphinic acids-from synthesis to properties and applications in separation processes. Molecules. 2020;25(18):4236. 10.3390/molecules25184236.Search in Google Scholar PubMed PubMed Central

[5] Kukkonen E, Virtanen EJ, Moilanen JO. α-Aminophosphonates, -phosphinates, and -phosphine oxides as extraction and precipitation agents for rare earth metals, thorium, and uranium: A review. Molecules. 2022;27(11):3465. 10.3390/molecules27113465.Search in Google Scholar PubMed PubMed Central

[6] Quin LD. A Guide to organophosphorus chemistry. New York: Wiley; 2000.Search in Google Scholar

[7] Kosolapoff GM, Huber WF. Synthesis of aromatic phosphonic acids and their derivatives. I. The derivatives of benzene, toluene and chlorobenzenes. J Am Chem Soc. 1947;69(8):2020–1. 10.1021/ja01200a059.Search in Google Scholar

[8] Dey NK, Hoque MEU, KimCK, Lee B-S, Lee HW. Kinetics and mechanism of the aminolysis of dimethyl and methyl phenyl phosphinic chlorides with anilines. J Phys Org Chem. 2009;22(5):425–30. 10.1002/poc.1478.Search in Google Scholar

[9] Hamzehee F, Pourayoubi M, Farhadipour A, Choquesillo-Lazarte D. Two new phosphinic amides: synthesis, crystal structure, and theoretical study of hydrogen bonding. Phosphorus Sulfur Silicon. 2016;192(3):359–67. 10.1080/10426507.2016.1239200.Search in Google Scholar

[10] Ou Y, Huang Y, He Z, Yu G, Huo Y, Li X, et al. A phosphoryl radical-initiated Atherton–Todd-type reaction under open air. Chem Commun. 2020;56(9):1357–60. 10.1039/C9CC09407E.Search in Google Scholar

[11] Tan Y, Han Y-P, Zhang Y, Zhang H-Y, Zhao J, Yang S-D. Primary amination of Ar2P(O)–H with (NH4)2CO3 as an ammonia source under simple and mild conditions and its extension to the construction of various P–N or P–O bonds. J Org Chem. 2022;87(5):3254–64. 10.1021/acs.joc.1c02933.Search in Google Scholar PubMed

[12] Jablonkai E, Henyecz R, Milen M, Kóti J, Keglevich G. T3P®- assisted esterification and amidation of phosphinic acids. Tetrahedron. 2014;70(44):8280–5. 10.1016/j.tet.2014.09.021.Search in Google Scholar

[13] Jablonkai E, Milen M, Drahos L, Keglevich G. Esterification of five-membered cyclic phosphinic acids under mild conditions using propylphosphonic anhydride (T3P®). Tetrahedron Lett. 2013;54(44):5873–5. 10.1016/j.tetlet.2013.08.082.Search in Google Scholar

[14] Keglevich G, Kiss NZ, Körtvélyesi T. Microwave-assisted functionalization of phosphinic acids: Amidations versus esterifications. Heteroat Chem. 2013;24(2):91–9. 10.1002/hc.21068.Search in Google Scholar

[15] Kiss NZ, Keglevich G. Microwave-assisted direct esterification of cyclic phosphinic acids in the presence of ionic liquids. Tetrahedron Lett. 2016;57(9):971–4. 10.1016/j.tetlet.2016.01.044.Search in Google Scholar

[16] Keglevich G, Kiss NZ, Mucsi Z, Körtvélyesi T. Insights into a surprising reaction: The microwave-assisted direct esterification of phosphinic acids. Org Biomol Chem. 2012;10(10):2011–8. 10.1039/C2OB06972E.Search in Google Scholar

[17] Kiss NZ, Keglevich G. Direct esterification of phosphinic and phosphonic acids enhanced by ionic liquid additives. Pure Appl Chem. 2019;91(1):59–65. 10.1515/pac-2018-1008.Search in Google Scholar

[18] Harsági N, Kiss NZ, Keglevich G. P-Chloride-free synthesis of phosphoric esters: microwave-assisted esterification of alkyl- and dialkyl phosphoric ester-acids obtained from phosphorus pentoxide. Synthesis. 2022;54(13):3047–54. 10.1055/a-1811-8586.Search in Google Scholar

[19] Kosolapoff GM. Preparation of some mixed dialkyl phosphites. J Am Chem Soc. 1951;73(10):4989. 10.1021/ja01154a528.Search in Google Scholar

[20] Froneman M, Modro TA. The titanium-mediated transesterification of phosphorous esters. Tetrahedron Lett. 1988;29(27):3327–30. 10.1016/0040-4039(88)85153-0.Search in Google Scholar

[21] Harsági N, Kiss NZ, Drahos L, Keglevich G. Synthesis of cyclic phosphinates by microwave-assisted ionic liquid-promoted alcoholysis. Synthesis. 2022;54(17):3899–905. 10.1055/a-1504-8924.Search in Google Scholar

[22] Kiss NZ, Henyecz R, Keglevich G. Continuous flow esterification of a H-phosphinic acid, and transesterification of H-phosphinates and H-phosphonates under microwave conditions. Molecules. 2020;25(3):719. 10.3390/molecules25030719.Search in Google Scholar PubMed PubMed Central

[23] Cook RD, Daouk WA, Hajj AN, Kabbani A, Kurku A, Samaha M, et al. The aminolysis of phosphinates; the kinetics and mechanism of the aminolysis of phosphinate esters in acetonitrile. Can J Chem. 1986;64(2):213–9. 10.1139/v86-037.Search in Google Scholar

[24] Dey NK, Kim CK, Lee HW. Kinetics and mechanism of the anilinolyses of aryl dimethyl, methyl phenyl and diphenyl phosphinates. Org Biomol Chem. 2011;9(3):717–24. 10.1039/c0ob00517g.Search in Google Scholar PubMed

[25] Um I, Shin Y, Han J. Aminolysis of X-substituted phenyl diphenylphosphinates: Effect of amine nature on reactivity and transition-state structure. J Org Chem. 2009;74(8):3073–8. 10.1021/jo900219t.Search in Google Scholar PubMed

[26] Ślusarska E, Zwierzak A. One-pot phase-transfer-catalyzed N-alkylation of diphenylphosphinamide with alcohols in the presence of methanesulfonyl chloride. Synthesis-Stuttgart. 1981;1981(2):155–6. 10.1055/s-1981-29374.Search in Google Scholar

[27] Keglevich G, Harsági N, Szilágyi S. Microwave-assisted, ionic liquid-catalyzed aminolysis and alcoholysis of phosphinic derivatives: the interconversion of phosphinates and phosphinic amides. Green Chem. 2023;25(24):10372–80. 10.1039/d3gc02711b.Search in Google Scholar

[28] Deng L, Wang Y, Mei H, Pan Y, Han J. Electrochemical dehydrogenative phosphorylation of alcohols for the synthesis of organophosphinates. J Org Chem. 2019;84(2):949–56. 10.1021/acs.joc.8b02882.Search in Google Scholar PubMed

[29] Zhou Y, Yang J, Chen T, Yin S-F, Han D, Han L-B. Stereospecific aerobic oxidative dehydrocoupling of P(O)–H bonds with amines catalyzed by copper. Bull Chem Soc Jpn. 2014;87(3):400–2. 10.1246/bcsj.20130310.Search in Google Scholar

[30] Li B-J, Simard RD, Beauchemin AM. o-Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P(=O)–NH containing compounds. Chem Commun. 2017;53:8667–70. 10.1039/c7cc04950a.Search in Google Scholar PubMed

[31] Hohmann E, Keglevich G, Greiner I. The effect of onium salt additives on the Diels-Alder reactions of a 1-phenyl-1,2-dihydrophosphinine oxide under microwave conditions. Phosphorus Sulfur Silicon. 2007;182(10):2351–7. 10.1080/10426500701441473.Search in Google Scholar

[32] Ullah Z, Khan AS, Muhammad N, Ullah R, Alqahtani AS, Shah SN, et al. A review on ionic liquids as perspective catalysts in transesterification of different feedstock oil into biodiesel. J Mol Liq. 2018;266:673–86. 10.1016/j.molliq.2018.06.024.Search in Google Scholar
Received: 2024-01-18
Accepted: 2024-04-09
Published Online: 2024-06-14

© 2024 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  40. Thermal treatment impact on the evolution of active phases in layered double hydroxide-based ZnCr photocatalysts: Photodegradation and antibacterial performance
  41. Preparation of silymarin-loaded zein polysaccharide core–shell nanostructures and evaluation of their biological potentials
  42. Preparation and characterization of composite-modified PA6 fiber for spectral heating and heat storage applications
  43. Preparation and electrocatalytic oxygen evolution of bimetallic phosphates (NiFe)2P/NF
  44. Rod-shaped Mo(vi) trichalcogenide–Mo(vi) oxide decorated on poly(1-H pyrrole) as a promising nanocomposite photoelectrode for green hydrogen generation from sewage water with high efficiency
  45. Green synthesis and studies on citrus medica leaf extract-mediated Au–ZnO nanocomposites: A sustainable approach for efficient photocatalytic degradation of rhodamine B dye in aqueous media
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  47. The analytical assessment of metal contamination in industrial soils of Saudi Arabia using the inductively coupled plasma technology
  48. The effect of modified oily sludge on the slurry ability and combustion performance of coal water slurry
  49. Eggshell waste transformation to calcium chloride anhydride as food-grade additive and eggshell membranes as enzyme immobilization carrier
  50. Synthesis of EPAN and applications in the encapsulation of potassium humate
  51. Biosynthesis and characterization of silver nanoparticles from Cedrela toona leaf extracts: An exploration into their antibacterial, anticancer, and antioxidant potential
  52. Enhancing mechanical and rheological properties of HDPE films through annealing for eco-friendly agricultural applications
  53. Immobilisation of catalase purified from mushroom (Hydnum repandum) onto glutaraldehyde-activated chitosan and characterisation: Its application for the removal of hydrogen peroxide from artificial wastewater
  54. Sodium titanium oxide/zinc oxide (STO/ZnO) photocomposites for efficient dye degradation applications
  55. Effect of ex situ, eco-friendly ZnONPs incorporating green synthesised Moringa oleifera leaf extract in enhancing biochemical and molecular aspects of Vicia faba L. under salt stress
  56. Biosynthesis and characterization of selenium and silver nanoparticles using Trichoderma viride filtrate and their impact on Culex pipiens
  57. Photocatalytic degradation of organic dyes and biological potentials of biogenic zinc oxide nanoparticles synthesized using the polar extract of Cyperus scariosus R.Br. (Cyperaceae)
  58. Assessment of antiproliferative activity of green-synthesized nickel oxide nanoparticles against glioblastoma cells using Terminalia chebula
  59. Chlorine-free synthesis of phosphinic derivatives by change in the P-function
  60. Anticancer, antioxidant, and antimicrobial activities of nanoemulsions based on water-in-olive oil and loaded on biogenic silver nanoparticles
  61. Study and mechanism of formation of phosphorus production waste in Kazakhstan
  62. Synthesis and stabilization of anatase form of biomimetic TiO2 nanoparticles for enhancing anti-tumor potential
  63. Microwave-supported one-pot reaction for the synthesis of 5-alkyl/arylidene-2-(morpholin/thiomorpholin-4-yl)-1,3-thiazol-4(5H)-one derivatives over MgO solid base
  64. Screening the phytochemicals in Perilla leaves and phytosynthesis of bioactive silver nanoparticles for potential antioxidant and wound-healing application
  65. Graphene oxide/chitosan/manganese/folic acid-brucine functionalized nanocomposites show anticancer activity against liver cancer cells
  66. Nature of serpentinite interactions with low-concentration sulfuric acid solutions
  67. Multi-objective statistical optimisation utilising response surface methodology to predict engine performance using biofuels from waste plastic oil in CRDi engines
  68. Microwave-assisted extraction of acetosolv lignin from sugarcane bagasse and electrospinning of lignin/PEO nanofibres for carbon fibre production
  69. Biosynthesis, characterization, and investigation of cytotoxic activities of selenium nanoparticles utilizing Limosilactobacillus fermentum
  70. Highly photocatalytic materials based on the decoration of poly(O-chloroaniline) with molybdenum trichalcogenide oxide for green hydrogen generation from Red Sea water
  71. Highly efficient oil–water separation using superhydrophobic cellulose aerogels derived from corn straw
  72. Beta-cyclodextrin–Phyllanthus emblica emulsion for zinc oxide nanoparticles: Characteristics and photocatalysis
  73. Assessment of antimicrobial activity and methyl orange dye removal by Klebsiella pneumoniae-mediated silver nanoparticles
  74. Influential eradication of resistant Salmonella Typhimurium using bioactive nanocomposites from chitosan and radish seed-synthesized nanoselenium
  75. Antimicrobial activities and neuroprotective potential for Alzheimer’s disease of pure, Mn, Co, and Al-doped ZnO ultra-small nanoparticles
  76. Green synthesis of silver nanoparticles from Bauhinia variegata and their biological applications
  77. Synthesis and optimization of long-chain fatty acids via the oxidation of long-chain fatty alcohols
  78. Eminent Red Sea water hydrogen generation via a Pb(ii)-iodide/poly(1H-pyrrole) nanocomposite photocathode
  79. Green synthesis and effective genistein production by fungal β-glucosidase immobilized on Al2O3 nanocrystals synthesized in Cajanus cajan L. (Millsp.) leaf extracts
  80. Green stability-indicating RP-HPTLC technique for determining croconazole hydrochloride
  81. Green synthesis of La2O3–LaPO4 nanocomposites using Charybdis natator for DNA binding, cytotoxic, catalytic, and luminescence applications
  82. Eco-friendly drugs induce cellular changes in colistin-resistant bacteria
  83. Tangerine fruit peel extract mediated biogenic synthesized silver nanoparticles and their potential antimicrobial, antioxidant, and cytotoxic assessments
  84. Green synthesis on performance characteristics of a direct injection diesel engine using sandbox seed oil
  85. A highly sensitive β-AKBA-Ag-based fluorescent “turn off” chemosensor for rapid detection of abamectin in tomatoes
  86. Green synthesis and physical characterization of zinc oxide nanoparticles (ZnO NPs) derived from the methanol extract of Euphorbia dracunculoides Lam. (Euphorbiaceae) with enhanced biosafe applications
  87. Detection of morphine and data processing using surface plasmon resonance imaging sensor
  88. Effects of nanoparticles on the anaerobic digestion properties of sulfamethoxazole-containing chicken manure and analysis of bio-enzymes
  89. Bromic acid-thiourea synergistic leaching of sulfide gold ore
  90. Green chemistry approach to synthesize titanium dioxide nanoparticles using Fagonia Cretica extract, novel strategy for developing antimicrobial and antidiabetic therapies
  91. Green synthesis and effective utilization of biogenic Al2O3-nanocoupled fungal lipase in the resolution of active homochiral 2-octanol and its immobilization via aluminium oxide nanoparticles
  92. Eco-friendly RP-HPLC approach for simultaneously estimating the promising combination of pentoxifylline and simvastatin in therapeutic potential for breast cancer: Appraisal of greenness, whiteness, and Box–Behnken design
  93. Use of a humidity adsorbent derived from cockleshell waste in Thai fried fish crackers (Keropok)
  94. One-pot green synthesis, biological evaluation, and in silico study of pyrazole derivatives obtained from chalcones
  95. Bio-sorption of methylene blue and production of biofuel by brown alga Cystoseira sp. collected from Neom region, Kingdom of Saudi Arabia
  96. Synthesis of motexafin gadolinium: A promising radiosensitizer and imaging agent for cancer therapy
  97. The impact of varying sizes of silver nanoparticles on the induction of cellular damage in Klebsiella pneumoniae involving diverse mechanisms
  98. Microwave-assisted green synthesis, characterization, and in vitro antibacterial activity of NiO nanoparticles obtained from lemon peel extract
  99. Rhus microphylla-mediated biosynthesis of copper oxide nanoparticles for enhanced antibacterial and antibiofilm efficacy
  100. Harnessing trichalcogenide–molybdenum(vi) sulfide and molybdenum(vi) oxide within poly(1-amino-2-mercaptobenzene) frameworks as a photocathode for sustainable green hydrogen production from seawater without sacrificial agents
  101. Magnetically recyclable Fe3O4@SiO2 supported phosphonium ionic liquids for efficient and sustainable transformation of CO2 into oxazolidinones
  102. A comparative study of Fagonia arabica fabricated silver sulfide nanoparticles (Ag2S) and silver nanoparticles (AgNPs) with distinct antimicrobial, anticancer, and antioxidant properties
  103. Visible light photocatalytic degradation and biological activities of Aegle marmelos-mediated cerium oxide nanoparticles
  104. Physical intrinsic characteristics of spheroidal particles in coal gasification fine slag
  105. Exploring the effect of tea dust magnetic biochar on agricultural crops grown in polycyclic aromatic hydrocarbon contaminated soil
  106. Crosslinked chitosan-modified ultrafiltration membranes for efficient surface water treatment and enhanced anti-fouling performances
  107. Study on adsorption characteristics of biochars and their modified biochars for removal of organic dyes from aqueous solution
  108. Zein polymer nanocarrier for Ocimum basilicum var. purpurascens extract: Potential biomedical use
  109. Green synthesis, characterization, and in vitro and in vivo biological screening of iron oxide nanoparticles (Fe3O4) generated with hydroalcoholic extract of aerial parts of Euphorbia milii
  110. Novel microwave-based green approach for the synthesis of dual-loaded cyclodextrin nanosponges: Characterization, pharmacodynamics, and pharmacokinetics evaluation
  111. Bi2O3–BiOCl/poly-m-methyl aniline nanocomposite thin film for broad-spectrum light-sensing
  112. Green synthesis and characterization of CuO/ZnO nanocomposite using Musa acuminata leaf extract for cytotoxic studies on colorectal cancer cells (HCC2998)
  113. Review Articles
  114. Materials-based drug delivery approaches: Recent advances and future perspectives
  115. A review of thermal treatment for bamboo and its composites
  116. An overview of the role of nanoherbicides in tackling challenges of weed management in wheat: A novel approach
  117. An updated review on carbon nanomaterials: Types, synthesis, functionalization and applications, degradation and toxicity
  118. Special Issue: Emerging green nanomaterials for sustainable waste management and biomedical applications
  119. Green synthesis of silver nanoparticles using mature-pseudostem extracts of Alpinia nigra and their bioactivities
  120. Special Issue: New insights into nanopythotechnology: current trends and future prospects
  121. Green synthesis of FeO nanoparticles from coffee and its application for antibacterial, antifungal, and anti-oxidation activity
  122. Dye degradation activity of biogenically synthesized Cu/Fe/Ag trimetallic nanoparticles
  123. Special Issue: Composites and green composites
  124. Recent trends and advancements in the utilization of green composites and polymeric nanocarriers for enhancing food quality and sustainable processing
  125. Retraction
  126. Retraction of “Biosynthesis and characterization of silver nanoparticles from Cedrela toona leaf extracts: An exploration into their antibacterial, anticancer, and antioxidant potential”
  127. Retraction of “Photocatalytic degradation of organic dyes and biological potentials of biogenic zinc oxide nanoparticles synthesized using the polar extract of Cyperus scariosus R.Br. (Cyperaceae)”
  128. Retraction to “Green synthesis on performance characteristics of a direct injection diesel engine using sandbox seed oil”
https://doi.org/10.1515/gps-2024-0014
Keywords for this article
phosphonates; aminolysis; phosphonic amides; alcoholysis; microwaves; green synthesis; chlorine-free synthesis
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BY 4.0

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  39. Optimization of biomass durian peel as a heterogeneous catalyst in biodiesel production using microwave irradiation
  40. Thermal treatment impact on the evolution of active phases in layered double hydroxide-based ZnCr photocatalysts: Photodegradation and antibacterial performance
  41. Preparation of silymarin-loaded zein polysaccharide core–shell nanostructures and evaluation of their biological potentials
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  51. Biosynthesis and characterization of silver nanoparticles from Cedrela toona leaf extracts: An exploration into their antibacterial, anticancer, and antioxidant potential
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  59. Chlorine-free synthesis of phosphinic derivatives by change in the P-function
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  66. Nature of serpentinite interactions with low-concentration sulfuric acid solutions
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  68. Microwave-assisted extraction of acetosolv lignin from sugarcane bagasse and electrospinning of lignin/PEO nanofibres for carbon fibre production
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  73. Assessment of antimicrobial activity and methyl orange dye removal by Klebsiella pneumoniae-mediated silver nanoparticles
  74. Influential eradication of resistant Salmonella Typhimurium using bioactive nanocomposites from chitosan and radish seed-synthesized nanoselenium
  75. Antimicrobial activities and neuroprotective potential for Alzheimer’s disease of pure, Mn, Co, and Al-doped ZnO ultra-small nanoparticles
  76. Green synthesis of silver nanoparticles from Bauhinia variegata and their biological applications
  77. Synthesis and optimization of long-chain fatty acids via the oxidation of long-chain fatty alcohols
  78. Eminent Red Sea water hydrogen generation via a Pb(ii)-iodide/poly(1H-pyrrole) nanocomposite photocathode
  79. Green synthesis and effective genistein production by fungal β-glucosidase immobilized on Al2O3 nanocrystals synthesized in Cajanus cajan L. (Millsp.) leaf extracts
  80. Green stability-indicating RP-HPTLC technique for determining croconazole hydrochloride
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  89. Bromic acid-thiourea synergistic leaching of sulfide gold ore
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  91. Green synthesis and effective utilization of biogenic Al2O3-nanocoupled fungal lipase in the resolution of active homochiral 2-octanol and its immobilization via aluminium oxide nanoparticles
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  94. One-pot green synthesis, biological evaluation, and in silico study of pyrazole derivatives obtained from chalcones
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  96. Synthesis of motexafin gadolinium: A promising radiosensitizer and imaging agent for cancer therapy
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  99. Rhus microphylla-mediated biosynthesis of copper oxide nanoparticles for enhanced antibacterial and antibiofilm efficacy
  100. Harnessing trichalcogenide–molybdenum(vi) sulfide and molybdenum(vi) oxide within poly(1-amino-2-mercaptobenzene) frameworks as a photocathode for sustainable green hydrogen production from seawater without sacrificial agents
  101. Magnetically recyclable Fe3O4@SiO2 supported phosphonium ionic liquids for efficient and sustainable transformation of CO2 into oxazolidinones
  102. A comparative study of Fagonia arabica fabricated silver sulfide nanoparticles (Ag2S) and silver nanoparticles (AgNPs) with distinct antimicrobial, anticancer, and antioxidant properties
  103. Visible light photocatalytic degradation and biological activities of Aegle marmelos-mediated cerium oxide nanoparticles
  104. Physical intrinsic characteristics of spheroidal particles in coal gasification fine slag
  105. Exploring the effect of tea dust magnetic biochar on agricultural crops grown in polycyclic aromatic hydrocarbon contaminated soil
  106. Crosslinked chitosan-modified ultrafiltration membranes for efficient surface water treatment and enhanced anti-fouling performances
  107. Study on adsorption characteristics of biochars and their modified biochars for removal of organic dyes from aqueous solution
  108. Zein polymer nanocarrier for Ocimum basilicum var. purpurascens extract: Potential biomedical use
  109. Green synthesis, characterization, and in vitro and in vivo biological screening of iron oxide nanoparticles (Fe3O4) generated with hydroalcoholic extract of aerial parts of Euphorbia milii
  110. Novel microwave-based green approach for the synthesis of dual-loaded cyclodextrin nanosponges: Characterization, pharmacodynamics, and pharmacokinetics evaluation
  111. Bi2O3–BiOCl/poly-m-methyl aniline nanocomposite thin film for broad-spectrum light-sensing
  112. Green synthesis and characterization of CuO/ZnO nanocomposite using Musa acuminata leaf extract for cytotoxic studies on colorectal cancer cells (HCC2998)
  113. Review Articles
  114. Materials-based drug delivery approaches: Recent advances and future perspectives
  115. A review of thermal treatment for bamboo and its composites
  116. An overview of the role of nanoherbicides in tackling challenges of weed management in wheat: A novel approach
  117. An updated review on carbon nanomaterials: Types, synthesis, functionalization and applications, degradation and toxicity
  118. Special Issue: Emerging green nanomaterials for sustainable waste management and biomedical applications
  119. Green synthesis of silver nanoparticles using mature-pseudostem extracts of Alpinia nigra and their bioactivities
  120. Special Issue: New insights into nanopythotechnology: current trends and future prospects
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  125. Retraction
  126. Retraction of “Biosynthesis and characterization of silver nanoparticles from Cedrela toona leaf extracts: An exploration into their antibacterial, anticancer, and antioxidant potential”
  127. Retraction of “Photocatalytic degradation of organic dyes and biological potentials of biogenic zinc oxide nanoparticles synthesized using the polar extract of Cyperus scariosus R.Br. (Cyperaceae)”
  128. Retraction to “Green synthesis on performance characteristics of a direct injection diesel engine using sandbox seed oil”
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