Design and preparation of HPW-anchored magnetic carbon nitride nanosheets: an efficient and eco-friendly nanocomposite for one-pot synthesis of α-amino phosphonates

Article abstract of DOI:10.1007/s11164-021-04545-0

Heterogeneous catalysis is one of the fastest and greatest developing branches and longstanding challenges in academic researchers and the chemical industry. Carbon-based material with various functional groups, the most abundant elements, and the main component in natural products provide a unique platform for heterogeneous catalysis due to their excellent biocompatibility and high performance. Herein, we introduce a novel nanocomposite comprising of different acids anchored to magnetic mesoporous carbon nitrides through a grindstone method to enhance nanocomposite catalysts’ environmentally benign capability. As a result, the obtained porous magnetic catalysts show the highest possible activity and product selectivity for facile preparation of α-amino phosphonates derivatives in good to excellent yields at ambient temperature. This fast and straightforward methodology offers pot economy for the satisfactory reaction of various aldehyde, amine, and triaryl and trialkyl phosphite with a broad range of functional groups in a gram scale under mild reaction conditions.

Full text of DOI:10.1007/s11164-021-04545-0

Research on Chemical Intermediates
https://doi.org/10.1007/s11164-021-04545-0
Design and preparation of HPW‑anchored magnetic
carbon nitride nanosheets: an efcient and eco‑friendly
nanocomposite for one‑pot synthesis of α‑amino
phosphonates
Asieh Azhdari1 · Najmedin Azizi1,2
Received: 13 May 2021 / Accepted: 15 July 2021
© The Author(s), under exclusive licence to Springer Nature B.V. 2021
Abstract
Heterogeneous catalysis is one of the fastest and greatest developing branches and
longstanding challenges in academic researchers and the chemical industry. Carbon-
based material with various functional groups, the most abundant elements, and the
main component in natural products provide a unique platform for heterogeneous
catalysis due to their excellent biocompatibility and high performance. Herein, we
introduce a novel nanocomposite comprising of diferent acids anchored to magnetic
mesoporous carbon nitrides through a grindstone method to enhance nanocomposite
catalysts’ environmentally benign capability. As a result, the obtained porous mag-
netic catalysts show the highest possible activity and product selectivity for facile
preparation of α-amino phosphonates derivatives in good to excellent yields at ambi-
ent temperature. This fast and straightforward methodology ofers pot economy for
the satisfactory reaction of various aldehyde, amine, and triaryl and trialkyl phos-
phite with a broad range of functional groups in a gram scale under mild reaction
conditions.
Keywords α-Amino phosphonate · g-C3N4 · Phosphotungstic acid · Kabachnik–
felds condensation · Magnetic carbon nitride nanocomposite
Introduction
Structural varieties of carbon compounds, namely activated carbon, graphite, gra-
phene, nanotube, and carbon nitride, have outstanding physicochemical, thermal,
and electrical properties. Their various applications as supports or catalysts are
*
Najmedin Azizi
azizi@ccerci.ac.ir
1
2
Department of Chemistry, Islamic Azad University, Ahvaz Branch, Ahvaz, Iran
Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
Vol.:(0123456789)
1 3

A. Azhdari, N. Azizi
becoming more prominent, as evidenced by recent literature reports in this area
[1–3]. Graphitic carbon nitride (g-C3N4) are usually considered the most appeal-
ing and attractive carbon-based polymers, with unique physicochemical proper-
ties such as excellent chemical stability, controllable chemical composition, and
economic benefts [4–6]. Due to these unique properties, g-C3N4 porous polymers
have been widely used in the artifcial photosynthesis, adsorbents, sensors, and
visible photocatalysis feld in recent years [7–9]. However, a common issue in the
practical application of bulk g-C3N4 is their unsatisfactory catalytic activity due
to the insufcient functional groups on the polymer’s surface. On the other hand,
scalable and straightforward functionalization/modifcation strategy in the g-C3N4
surface because of the rigid template is difcult hardly possible [6, 10–15]. In this
context, tremendous research and extensive investigations have been reported on
the functional modifcations of g-C3N4 using exfoliation, doping, and hybridizing
to enhance catalytic performance [16–27]. On the other hand, there is no report
on the g-C3N4 nanocomposite preparation via mechanical grinding in the litera-
ture. Herein, we fabricated g-C3N4 nanocomposite with diferent Lewis and Bron-
sted acid in a more straightforward manner and were explored for the greener
production of α-amino phosphonates.
Phosphonates and phosphonic acids are highly stable phosphorus-containing
compounds and play an essential role in the cell’s physiological activity [28–30].
α-Aminophosphonates are privileged compounds in the design of pharmaceuti-
cally active compounds and valuable building blocks in constructing organophos-
phate pesticides, dyes, and functional materials [31]. Furthermore, α-amino phos-
phonates fnd extensive use as an anticancer, antibacterial, antitumor drug, plant
growth regulator, and enzyme inhibitor [32, 33].
Arbuzov discovered alkyl phosphonates in 1906 [34, 35], and subsequently,
Osipova made N-alkoxy α-amino phosphonates from the reaction of trimethyl
phosphite and oxime. Among diferent approaches to forming α-amino phos-
phonates, the Kabachnik–Fields and aza-Pudovik reactions have been accepted
as convenient and essential routes in the literature. The Kabachnik –Fields reac-
tion was the most extensively studied as an excellent mild method that afords
α-amino phosphonates in acceptable yields with the catalyst system’s proper
choice. In this context, many catalysts, including ionic liquids, nanocatalysts,
metal catalysts, commercial Bronsted, and Lewis acid, organic functionalized
polymers, have been devoted to promoting its reactions [36–39]. Among the
reported methods, the nucleophilic addition of dimethyl phosphite and trimethyl
phosphite to iminium salts or imines is more convenient. Imine formation was
very rapid and straightforward and usually activated both acidic and basic media.
However, in these approaches, the catalyst is used in over stoichiometric quanti-
ties. The procedures frequently requested a purifcation step and less satisfactory
from the perspective of chemical efciency and eco-friendliness. The substrate
scope is limited to a few raw materials, particularly trialkyl phosphites, typically
considered superior nucleophiles [40–42].
In recent years, our research has been interested in designing a new eco-friendly
system using environmentally friendly solvents and benign catalysts in organic trans-
formations [43–46]. Herein, we report a straightforward and fast preparation of aryl/
1 3

Design and preparation of HPW-anchored magnetic carbon nitride…
alkyl α-amino phosphonates by one-pot reaction of carbonyl compounds, amines,
and phosphite derivatives promoted by magnetic carbon nitride nanocomposite.
Experimental
Chemicals and reagents
All commercial reagents and solvents were supplied from Merck, Germany, and
1
used as received. The H and 13C NMR spectra were recorded by a Bruker Avance
1
(500 MHz for H and 125 MHz for 13C). H3PW12O40 was purchased from Aldrich.
Fe3O4 and g-C3N4 were synthesized according to our previous work [23]. Melting
points were recorded on a Buchi R-535 apparatus.
General procedure for the preparation of g‑C3N4
Bulk g-C3N4 was by a facile thermal treatment of melamine source [23]. In brief,
10 g of melamine was heated at 550 °C for 3 h at a ramp rate of 5 °C/min. The
g-C3N4 nanosheets were exfoliated from bulk g-C3N4 under air.
Fabrication of HPW@Fe3O4/g‑C3N4 nanocomposite
0.7 g C3N4 and 0.3 g Fe3O4 were ground in mortar for 3 min. After that, 0.3 g phos-
phor tungstic acid (H3PW12O40 =HPW) was added and ground by mortar until pro-
duced black powder of HPW@Fe3O4/g-C3N4.
General procedure for the preparations of α‑amino phosphonates
In a test tube with a mechanical stirrer, aniline (0.5 mmol), benzaldehyde
(0.5 mmol), triphenyl, or trialkyl phosphite (0.5 mmol), HPW@Fe3O4/g-C3N4
(10 mg), and ethanol (1 mL) were added. The mixture was stirred at room tempera-
ture for 60 min until completion (followed by TLC analysis of reaction aliquots)
then 10 mL of ethyl acetate was introduced. The magnetic nanocomposite was sepa-
rated with an external magnet and washed with ethyl acetate and applied for the
next runs. Recrystallization of the mother liquor to aford the α-amino phosphonates
derivatives as pure products.
Result and discussion
The HPW@Fe3O4/g-C3N4 nanocomposite has been successfully prepared in two
steps. This straightforward two-step process involves syntheses of the g-C3N4
nanosheet support and grafting Fe3O4 and HPW over the layers of g-C3N4, respec-
tively. The surface morphologies of the resulting HPW@Fe3O4/g-C3N4 nano-
composites were investigated by scanning electron microscope (SEM). The SEM
1 3

A. Azhdari, N. Azizi
analysis is depicted in Fig. 1. The SEM image of HPW@Fe3O4/g-C3N4 nanocom-
posite showed small sheet-like nanoparticles with holes on the g-C3N4. Further-
more, it can be observed that Fe3O4 and HPW nearly spherical or slightly irregular
structures with small particles attached to the sheet layer of g-C3N4.
The energy-dispersive X-ray spectra (EDS) of HPW@Fe3O4/g-C3N4 are pre-
sented in Fig. 2. It can be seen in Fig. 2 that the presence of P, W, O, C, and N
elements, implying that the HPW and Fe3O4 are uniformly coated on the g-C3N4
surfaces.
The Fourier transformed infrared spectroscopy (FTIR) also confrmed functional
groups of the HPW@Fe3O4/g-C3N4 nanocomposite (Fig. 3). The characteristic
peaks were shown at 1235.34, 1320.52, 1408.78, 1634, and 804.92 cm−1 for typical
vibrations of heptazine-based molecular units of C=N and C–N in g-C3N4. FT-IR
peaks at 3432 cm−1 correspond to the N–H and NH2 groups of g-C3N4 and the O–H
groups due to the adsorption of water from the environments. The peak was shown
HPW
HPW
Fe
3O4
N
g-C3
4
N
g-C3
4
Fe
3O4
HPW
N
g-C3
4
Fe
3O4
HPW
Fig. 1 SEM of HPW@Fe3O4/g-C3N4 nanocomposite
1 3

Design and preparation of HPW-anchored magnetic carbon nitride…
Fig. 2 EDX analysis of HPW@Fe3O4/g-C3N4 nanocomposite
80
80
79
78
77
76
75
582.47cm-1
805.88cm-1
3432.42cm-1
74
73
72
1634.54cm-1
1406.54cm-1
1319.98cm-1
1237.66cm-1
71
71
4000
3500
3000
2500
2000
1500
1000
500 400
cm-1
Fig. 3 FT-IR spectra of HPW@Fe3O4/g-C3N4 nanocomposite
at 582 cm−1 for Fe3O4. The peak was shown at 950 cm−1 cm for P–O and the peaks
were shown at 691 and 805 cm−1 for W–O in phosphotungstic acid.
To further analyze the surface composition and structure of HPW@Fe3O4/g-
C3N4, XRD analysis was carried out (Fig. 4).The XRD pattern of HPW@Fe3O4/
g-C3N4 conforms structure of the g-C3N4, phosphortungstic acid, and Fe3O4. As
shown in Fig. 4, six refections are observed in the XRD pattern of Fe3O4 31.19,
35.43, 44.7, 53.27, 57.03 and 62.6° that belong to the (2 2 0), (3 1 1), (4 0 0), (4 2 2),
(5 1 1) and (4 4 0) plane difractions of Fe3O4, in addition to the observed refections
1 3

A. Azhdari, N. Azizi
Fig. 4 The XRD spectra of HPW@Fe3O4/g-C3N4 nanocomposite
at 23.11, 24.85, 25.3 and 34.52 that belong to the (0 0 2), (0 2 0), (2 0 0) and (2 0 2)
plane difractions of WO3. Furthermore, seven six refections are observed in 29.39,
37.1, 40.6, 44.7, 47.88, 49.6 and 57.03° that belong to the (2 0 1), (1 0 5), (1 0 7),
(2 0 7), (2 0 6), (3 0 4) and (3 1 4) plane difractions of PO4. The two characteristic
peaks at 13.1 and 27.4° identifed the typical layered C–N structure of g-C3N4.
Figure 5 shows a typical magnetization curve of HPW@Fe3O4/g-C3N4 nanocom-
posite and Fe3O4 nanoparticles at room temperature. The magnetization of the com-
posite was entirely saturated at high felds and the saturation magnetizations of pure
Fe3O4 and HPW@Fe3O4/g-C3N4 were 42.5 and 24.6 emu/g, respectively. Due to the
functionalization by HPW and g-C3N4, the decrease in the saturation magnetization
of composite, compared with pure Fe3O4 was observed. The strong magnetization of
the composite can completely meet the requirement of the magnetic separation from
the reaction system with an external magnet.
The synthesized nanocomposite catalytic activity was evaluated by synthe-
sizing α-(phenylamino) benzyl phosphonates in the model system to adjust the
reaction parameters (Table 1). In the model system, aniline (0.5 mmol), benza-
ldehyde (0.5 mmol) and triphenyl phosphite (0.5 mmol), ethanol (1 mL), and
various kinds of g-C3N4-based catalyst were added. When the reaction was per-
formed in the absence of catalyst for 80 min at room temperature, it was found
that only 13% yield and the starting materials along with imine intermediate were
recovered. Subsequently, a broad diversity of g-C3N4 derivatives was synthesized
to study their activity in the preparation of α-(phenylamino) benzyl phospho-
nates. Among several kinds of g-C3N4 nanocomposites, HPW@Fe3O4/g-C3N4
(Table 1, entry 14) was the most efective catalyst since it resulted in the highest
1 3

Design and preparation of HPW-anchored magnetic carbon nitride…
Fig. 5 VSM result of Fe3O4 and HPW@Fe3O4/g-C3N4
transformation to the desired phosphonate 4a. The catalytic performance of nano-
composite elements, namely g-C3N4, Fe3O4, and HPW, was also examined. The
results showed that nanocomposite elements were able to promote the model
reaction in moderate yields (Table 1, entries 8–10 and 23–25). The results mani-
fested that 10 mg of the composite was suitable to catalyze the model reaction in
excellent yields (Table 1, entry 14) and a higher amount of composite (30, 50 mg)
did not have notable efect on the model reaction (Table 1, entry 15, 16). Vari-
ous protic and aprotic organic solvents were frst examined. The results showed
that ethanol was the most favorable media (Table 1, entries 14) among the tested
solvents (Table 1, entries 18–22). The model reaction was ultimately best carried
out using 0.5 mmol of aniline, 0.5 mmol of benzaldehyde, 0.5 mmol of triphenyl
phosphite, and 10 mg of nanocomposite in ethanol for 60 min at room tempera-
ture (Table 1, entry 14).
After determining the optimized condition, various reactions using aniline deriv-
atives and aliphatic/aromatic carbonyl compounds with trialkyl/triphenyl phosphite
in the presence of 10 mg of HPW@Fe3O4/g-C3N4 were performed to identify gener-
alities and limitations of the procedure (Table 2). The one-pot synthesis of α-amino
phosphonates derivatives was succeeded from the reaction of various aromatic
aldehydes, aniline derivatives, and phosphite sources in good to excellent yields.
The reactions proceeded under mild conditions with a low reusable catalyst load-
ing in a simpler manner. A range of aniline derivatives with electron-withdrawing
groups and electron-donating groups underwent a one-pot reaction with aromatic
aldehydes, afording various aryl and alkyl phosphonates at room temperature under
short reaction times (Table 2).
The survey of Table 2 was shown us when electron-withdrawing groups on ben-
zaldehyde (Table 2, entries 3, 5, and 7), the yield was increased and when electron-
donating groups on benzaldehyde (Table 2, entries 2 and 4), the yield was decreased.
1 3

A. Azhdari, N. Azizi
Table 1 Synthesis of α-(phenylamino) benzyl phosphonates in the model conditions
Entry Catalysts
Amount of
time (min) Solvent
Temp. (°C) Yield (%)
catalyst (mg)
1
2
3
4
5
6
7
8
Without catalyst
g-C3N4
–
80
80
80
80
80
80
80
80
80
80
80
80
80
80
80
80
60
60
60
60
60
60
60
60
60
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Methanol
Acetonitrile
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
60
25
25
13
28
14
47
42
53
61
31
73
64
79
78
80
94
85
82
94
82
78
76
74
79
20
28
45
30
30
30
30
30
30
30
30
30
H2SO4@g-C3N4
HCl@g-C3N4
NH2SO3H@g-C3N4
Basic Al2O3@g-C3N4
CF3COOH@g-C3N4
Fe3O4/g-C3N4
HPW/g-C3N4
HPW@Fe3O4
Fe3O4/ZnCl2@g-C3N4 30
Fe3O4/NiCl2@g-C3N4 30
Fe3O4/WCl6@g-C3N4
HPW@Fe3O4/g-C3N4
HPW@Fe3O4/g-C3N4
HPW@Fe3O4/g-C3N4
HPW@Fe3O4/g-C3N4
HPW@Fe3O4/g-C3N4
HPW@Fe3O4/g-C3N4
HPW@Fe3O4/g-C3N4
HPW@Fe3O4/g-C3N4
HPW@Fe3O4/g-C3N4
g-C3N4
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
30
10
30
50
10
10
10
10
10
10
10
10
10
Ethyl acetate 25
H2O
THF
Ethanol
Ethanol
Ethanol
25
25
25
25
25
Fe3O4
HPW
When cyclohexanone and acetophenone as carbonyl groups were investigated
in the model reaction, no conversion was observed (Table 2, entries 13, 14). To
ensure this inception, two competition reactions denoted: (1) reaction between
0.5 mmol benzaldehyde, 0.5 mmol cyclohexanone, 0.5 mmol anilines, and
0.5 mmol triphenyl phosphite, (2) reaction between 0.5 mmol benzaldehyde, 0.5
cyclohexanone, 1 mmol aniline, and 1 mmol triphenyl phosphite. The investiga-
tion in reaction results has shown that cyclohexanone would not react, and it is
related to the chemoselectivity of the reaction.
1 3

Design and preparation of HPW-anchored magnetic carbon nitride…
Table 2 Synthesis of α-(phenylamino) benzyl phosphonate derivatives by HPW@Fe3O4/g-C3N4 nano-
catalyst
Entry Benzaldehyde
Aniline
2a
Phosphite Yield (%) M.P Found Rep
References
[30]
1
2
1a
3a
3b
94
91
142–144;
144–14630
148–150:
[48]
150–15148
3
4
5
3a
3c
3b
93
91
95
160–162:
[30]
158–15930
125–126:
[48]
126–12748
133–135: 135–136 [34]
34
6
7
3b
3a
92
94
163–164:
[38]
[48]
164–16638
130–131:
130–13148
8
9
3c
92
93
66–67: 64–6531
[31]
3b
91–93:92.5–94.528 [28]
1 3

A. Azhdari, N. Azizi
Table 2 (continued)
Entry Benzaldehyde
10
Aniline
Phosphite Yield (%) M.P Found Rep
References
[38]
3c
87
129–130: 12838
11
12
3b
3c
90
69
90–92: 88–9038
[38]
[38]
122–124:
124–12638
13
14
3a
3a
Trace
Trace
–
–
Based on the above results, a plausible reaction mechanism of the Kabach-
nik–Fields reaction in the presence of HPW@Fe3O4/g-C3N4 nanocomposite is
shown in Fig. 6. Initially, the carbonyl group of the aldehyde is activated by the
nanocatalyst to react with the amine to form the imine product [1]. In the next
step, the phosphite nucleophile is added to the resultant activated imine by the
HPW supported on the g-C3N4 to give phosphonium intermediate [2] which then
undergoes reaction with water to give α-amino phosphonates (Fig. 6).
The reusability of HPW@Fe3O4/g-C3N4 for the synthesis of α-(phenylamino)
benzyl phosphonate was also investigated. After completing the reaction, the
magnetic catalyst was removed with an external magnetic feld and washed with
ethanol and ethyl acetate. Subsequently, the catalyst was dried at 60 °C under
vacuum and applied to the fve successive runs without any signifcant change
in the catalytic efciency (Fig. 7). The heterogeneity of the nanocomposite was
studied by XRD and EDS spectroscopy, representing that there is virtually no
HPW-leaching (Figs. 8, 9).
1 3

Design and preparation of HPW-anchored magnetic carbon nitride…
Fig. 6 The proposed mechanism of the Kabachnik–Fields reaction in the presence of HPW@Fe3O4/g-
C3N4 nanocomposite
Fig. 7 Recyclability of HPW@Fe3O4/g-C3N4 nanocatalyst for synthesis of α-(phenylamino) benzyl phos-
phonate
Conclusion
In summary, an environmentally friendly magnetic carbon nitride catalyst,
namely HPW@Fe3O4/g-C3N4 nanocomposite, was prepared by immobilization
of HPW and Fe3O4 onto the g-C3N4 by grinding methods. By using this mag-
netic nanocomposite, the high-yielding three-component Kabachnik–Fields reac-
tion was successfully achieved. This method provides notable advantages such as
1 3

A. Azhdari, N. Azizi
Fig. 8 FT-IR spectra of reused HPW@Fe3O4/g-C3N4 nanocomposite
90As32
700
600
500
400
300
200
100
0
4
10
20
30
40
50
60
70
2-Theta - Scale
Fig. 9 The XRD spectra of reused HPW@Fe3O4/g-C3N4 nanocomposite
easy product separation and purifcation, excellent yields, short reaction times, a
small amount of the catalyst. The magnetic catalyst could be separated easily and
reused without a noticeable loss of catalytic activity.
Acknowledgements Financial support of this work by the Chemistry and Chemical Engineering
Research Center of Iran is gratefully appreciated.
1 3

Design and preparation of HPW-anchored magnetic carbon nitride…
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