Ultrasound assisted green synthesis of α-hydroxyphosphonates under solvent-free conditions

Article abstract of DOI:10.1007/s11164-015-2420-8

Abstract: A simple, efficient and environmentally benign method for the synthesis of α-hydroxyphosphonates by reaction of an aldehyde or a ketone, and trialkylphosphite is effectively accomplished under ultrasound irradiation and solvent-free and catalyst

Full text of DOI:10.1007/s11164-015-2420-8

Res Chem Intermed
DOI 10.1007/s11164-015-2420-8
Ultrasound assisted green synthesis of a-
hydroxyphosphonates under solvent-free conditions
Abdeslem Bouzina1 Nour-eddine Aouf1
•
•
Malika Berredjem1
Received: 17 October 2015 / Accepted: 31 December 2015
Ó Springer Science+Business Media Dordrecht 2016
Abstract A simple, efficient and environmentally benign method for the synthesis of
a-hydroxyphosphonates by reaction of an aldehyde or a ketone, and trialkylphosphite is
effectively accomplished under ultrasound irradiation and solvent-free and catalyst-free
conditions. This rapid method produces a-hydroxyphosphonates in high yields and short
reaction times.
Graphical Abstract
Electronic supplementary material The online version of this article (doi:10.1007/s11164-015-2420-8)
contains supplementary material, which is available to authorized users.
&
Malika Berredjem
mberredjem@yahoo.fr; malika.berredjem@univ-annaba.org
1
Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling
Group, Department of Chemistry, Sciences Faculty, Badji-Mokhtar - Annaba University,
Box 12, 23000 Annaba, Algeria
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A. Bouzina et al.
Keywords a-Hydroxyphosphonates Á Green chemistry Á Ultrasound irradiation Á
Solvent-free
Introduction
The synthesis of a-hydroxyphosphonates and their derivatives has attracted much
attention due to their potential biological activities with broad applications as
synthetic intermediates [1–8]. They exhibit a variety of interesting and useful
properties that make them attractive as herbicides [9], antibiotics [10], pesticides
[11], and antiviral [12] and anticancer agents [13].
Recently, various methodologies have been developed for the synthesis of a-
hydroxyphosphonates from aldehydes [14–17]. Most of them have reported the use of
expensive catalysts, strong acidic or basic conditions, higher temperatures, longer
reaction times and have required stoichiometric amount of reagents. These include
various bases such as sodium alkoxide [18], triethylamine [19], ethyl magnesium
bromide [20], potassium or cesium fluoride [21], LDA [22], MgO [23] etc., or acid
catalyst such as BF3 Et2O and AlCl3 or HCl [24], alumina [25], TFA or TfOH [26],
Ti(OiPr) [27], and other catalyst complexes such as chiral tethered bis (8-quinolinolato)
(TBOx) aluminum(III) [28], ambertlyst [29], lanthanide amides [(Me3Si)2N] 3Ln(l-
Cl)Li(THF)3 [6] and 1,4-dimethylpiperazine under ultrasonic irradiation [30].
One of the current major difficulties is to develop synthetic methods that are less
polluting, i.e., to design green chemical transformations and clean technology. In this
context, the use of ultrasonic irradiation to accelerate reactions has proven to be a
particularly important tool for meeting the green chemistry goals of minimization of
waste and reduction of energy requirements [31–36]. Applications have been found in
synthetic chemistry, in materials science, in life sciences, as well as in medicinal
chemistry [37, 38]. Improvement of chemical reactions by ultrasound is often
ascribed to the high temperature formed when cavitations formed by the ultrasound
collapse, sometimes leading to products different than those obtained without
sonication. Although the energy delivered through the cleansing bath is not that high,
there is still acoustic cavitation in the reaction flask. In heterogeneous systems, the
acoustic cavitation is known to vastly improve diffusion rates and accelerate the
reactions through micro jets formed from asymmetrical collapses of the bubbles, and
similar effects can be achieved with high speed mechanical stirring.
We report herein a highly efficient reaction for the synthesis of a-hydroxyphos-
phonates 1-13a, 1-2b and 1-3c under ultrasound irradiation and catalyst-free and
solvent-free conditions in high yields.
Experimental
General
All chemicals and solvents were purchased from common commercial sources and
were used as received without any further purification. All reactions were monitored
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Ultrasound assisted green synthesis of a…
by thin-layer chromatography (TLC) on silica Merck 60 F254 percolated aluminium
plates and were developed by spraying with ninhydrin solution. Column
chromatography was performed with Merck silica gel (230–400 mesh). Proton
nuclear magnetic resonance (1H NMR) spectra were recorded on a Bru¨cker
spectrometer at 250 or 400 MHz. Chemical shifts are reported in d units (ppm) with
TMS as reference (d 0.00). All coupling constants (J) are reported in Hertz.
Multiplicity is indicated by one or more of the following: s (singlet), d (doublet), t
(triplet), q (quartet), m (multiplet). Carbon nuclear magnetic resonance (13C NMR)
spectra were recorded on a Bru¨cker at 60 or 100 MHz. Phosphorus nuclear magnetic
resonance (31P NMR) spectra were recorded on a Bru¨cker at 60 or 100 MHz.
Chemical shifts are reported in d units (ppm) relative to CDCl3 (d 77.0). Infrared
spectra were recorded on a Perkin Elmer 600 spectrometer. Mass spectra were
recorded on a Shimadzu QP 1100 Ex mass spectrometer operating at an ionization
potential of 70 eV. Elemental analysis was recorded on a EURO E.A 3700. Melting
points were recorded on a Bu¨chi B-545 apparatus in open capillary tubes.
Ultrasound assisted reactions were carried out using a FUNGILAB ultrasonic bath
with a frequency of 40 kHz and a nominal power of 250 W. The reactions were
carried out in an open glass tube (diameter: 25 mm; thickness: 1 mm; volume:
20 mL) at room temperature.
Typical experimental procedure for the synthesis
of a-hydroxyphosphonates
In a glass tube (diameter: 25 mm; thickness: 1 mm; volume: 20 mL), a mixture of
aldehyde (1 mmol) and trialkylphosphite (1.2 mmol) was subjected to sonication
for appropriate time (Tables 1, 2, 3). After completion of the reaction, as indicated
by TLC, silica gel; dichloromethane:methanol (90:10) and a (6:4) mixture of diethyl
ether and n-hexane was added to the reaction mixture and pure product was
crystallized by cooling the solution to 6 °C overnight.
Diethyl (hydroxy(phenyl)methyl)phosphonate (1a, C11H17O4P)
Cristal; 94 % yield; 31P NMR (100 MHz, CDCl3): d = 21.44 ppm; 1H NMR
(400 MHz, CDCl3): d = 1.20 (t, J = 7.20 Hz, 3H, CH3-CH2O), 1.25 (t,
J = 6.93 Hz, 3H, CH3-CH2O), 3.90–3.96 (m, 2H, CH2-O), 3.97–4.07 (m, 2H,
CH2-O), 5.02 (d, J = 11.2 Hz, 1H, CH*), 7.25–7.37 (m, 3H, H-Ar), 7.46–7.49 (m,
2H, H-Ar). pm; 13C NMR (100 MHz, CDCl3): d = 16.53, 16.58, 63.26, 63.55,
70.22, 71.80, 127.27, 128.26, 128.44, 130.30, 136.80, 136.82 ppm; IR (KBr):
m = 3382.45, 1514.49, 1251.33, 1033.44 cm-1; MS: (m/z) = 245.1 (M ? 1); Anal.
Calc. for C11H17O4P: C, 54.10; H, 7.02; Found: C, 54.16; H, 7.03.
Diethyl (hydroxy(4-chlorophenyl)methyl)phosphonate (2a, C11H16ClO4P)
Cristal; 91 % yield; 31P NMR (100 MHz, CDCl3): d = 21.21 ppm; 1H NMR
(250 MHz, CDCl3): d = 1.16 (t, J = 7.16 Hz, 3H,CH3-CH2O), 1.23 (t,
J = 7.04 Hz, 3H, CH3-CH2O), 3.88 (m, 2H, CH2-O), 3.96 (m, 2H, CH2-O), 5.00
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A. Bouzina et al.
Table 1 Synthesis of a-hydroxyphosphonates from aldehydes
Entry
Aldehyde
Product
Time (min)
Yield %
1a
10
94
2a
3a
12
15
91
90
4a
5a
6a
7a
17
17
12
14
88
93
89
88
8a
13
10
92
94
9a
10a
10
15
92
90
11a
12a
13a
14
15
91
87
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Ultrasound assisted green synthesis of a…
Table 2 Synthesis of a-hydroxyphosphonates from isatin
Entry
isatin
Product
Time (min)
35
Yield %
85
1b
2b
37
86
Table 3 Synthesis of a-hydroxyphosphonates from ketones
Entry
Ketone
Product
Time (min)
27
Yield %
85
1c
35
25
84
85
2c
3c
(d, J = 10.13 Hz, 1H, CH*), 7.31–7.45 (m, 4H, H-Ar), ppm; 13C NMR (100 MHz,
CDCl3): d = 16.15, 16.51, 61.21, 62.35, 69.04, 70.75, 120.15, 125.17, 126.45,
132.45, 136.50 ppm; IR (KBr): m = 3249.69, 1491.85, 1234.20, 1029.13 cm-1
MS: (m/z) = 279 (M ? 1); Anal. Calc. for C11H16ClO4P: C, 47.41; H, 5.79; Found:
C, 47.37; H, 5.78.
;
Diethyl (hydroxy(2-chlorophenyl)methyl)phosphonate (3a, C11H16ClO4P)
Color powder; 90 % yield; 31P NMR (100 MHz, CDCl3): d = 21.45 ppm; 1H NMR
(250 MHz, CDCl3): d = 1.21 (t, J = 7.21 Hz, 3H,CH3-CH2O), 1.29 (t,
J = 7.06 Hz, 3H, CH3-CH2O), 3.91 (m, 2H, CH2-O), 4.02 (m, 2H, CH2-O), 5.08
(d, J = 10.81 Hz, 1H, CH*), 7.31–7.42 (m, 4H, H-Ar), ppm; 13C NMR (75 MHz,
CDCl3): d = 16.30, 16.75, 59.87, 60.20, 68.87, 69.25, 122.65, 124.39, 125.63,
133.15, 134.00 ppm; IR (KBr): m = 3319.75, 1614.61, 1254.76, 1056.29 cm-1
;
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A. Bouzina et al.
MS: (m/z) = 279 (M ? 1); Anal. Calc. for C11H16ClO4P: C, 47.41; H, 5.79; Found:
C, 47.42; H, 5.83.
Dimethyl (hydroxy(4-bromophenyl)methyl)phosphonate (4a, C9H12BrO4P)
White powder; 88 % yield; 31P NMR (100 MHz, CDCl3): d = 21.45 ppm; 1H
NMR (250 MHz, CDCl3): d = 3.91 (d, J = 9.61 Hz, 3H, CH3-O), 3.95 (d,
J = 10.12 Hz, 3H, CH3-O), 5.08 (d, J = 10.81 Hz, 1H, CH*), 7.15–7.40 (m, 4H,
H-Ar), ppm; 13C NMR (75 MHz, CDCl3): d = 53.17, 53.74, 72.61, 76.65, 127.08,
127.11, 127.65, 129.36, 137.97 ppm; IR (KBr): m = 3362.24, 1415.85, 1225.35,
1066.21 cm-1; MS: (m/z) = 293.9 (M ? 1); Anal. Calc. for C9H12BrO4P: C, 36.63;
H, 4.10; Found: C, 36.70; H, 4.13.
Dimethyl (hydroxy(4-methoxyphenyl)methyl)phosphonate (6a, C10H15O5P)
White powder; 89 % yield; 31P NMR (100 MHz, CDCl3): d = 21.61 ppm; 1H
NMR (250 MHz, CDCl3): d = 3.61 (d, J = 9.11 Hz, 3H,CH3-O), 3.79 (d,
J = 10.81 Hz, 3H, CH3-O), 3.82 (s, 3H, CH3-O), 5.02 (d, J = 14.81 Hz, 1H,
CH*), 7.01–7.35 (m, 2H, H-Ar), 7.37–7.48 (m, 2H, H-Ar) ppm; 13C NMR (75 MHz,
CDCl3): d = 53.82, 53.94, 55.40, 69.98, 71.54, 114.02, 120.40, 128.55, 128.64,
ppm; IR (KBr): m = 3319.75, 1479.54, 1235.79, 1066.29 cm-1; MS: (m/z) = 247
(M ? 1); Anal. Calc. for C10H15O5P: C, 48.78; H, 6.14; Found: C, 48.81; H, 6.09.
Diethyl (hydroxy(4-fluorophenyl)methyl)phosphonate (8a, C11H16FO4P)
White powder; 92 % yield; 31P NMR (100 MHz, CDCl3): d = 20.90 ppm; 1H
NMR (250 MHz, CDCl3): d = 1.17 (t, J = 7.07 Hz, 3H,CH3-CH2O), 1.23 (t,
J = 6.96 Hz, 3H, CH3-CH2O), 3.97 (m, 2H, CH2-O), 4.01 (m, 2H, CH2-O), 5.05 (d,
J = 10.78 Hz, 1H, CH*), 7.28–7.53 (m, 4H, H-Ar) ppm; 13C NMR (75 MHz,
CDCl3): d = 16.23, 16.71, 64.30, 65.70, 69.85, 70.61, 119.87, 121.20, 122.60,
126.55, 131.20, 134.51, 157.23 ppm; IR (KBr): m = 3273.39, 1416.56, 1239.88,
1066.06 cm-1; MS: (m/z) = 263 (M ? 1); Anal. Calc. for C11H16FO4P: C, 50.39;
H, 6.15; Found: C, 50.42; H, 6.13.
Diethyl (1-hydroxy-3-phenylpropyl)phosphonate (12a, C13H21O4P)
White powder; 91 % yield; 31P NMR (100 MHz, CDCl3): d = 20.20 ppm; 1H
NMR (250 MHz, CDCl3): d = 1.18 (t, J = 7.24 Hz, 3H,CH3-CH2O), 1.25 (t,
J = 6.99 Hz, 3H, CH3-CH2O), 1.75 (m, 2H, CH2-CH), 2.68 (m, 2H, CH2-Ar), 3.94
(m, 2H, CH2-O), 4.10 (m, 2H, CH2-O), 5.12 (d, J = 10.85 Hz, 1H, CH*), 7.31–7.39
(m, 3H, H-Ar), 7.43–7.46 (m, 2H, H-Ar) ppm; 13C NMR (100 MHz, CDCl3):
d = 16.53, 16.58, 25.30, 34.7, 63.26, 63.55, 70.22, 71.80, 127.27, 128.26, 128.44,
130.30, 136.80, 136.82 ppm; IR (KBr): m = 3325.97, 1514.29, 1250.96,
1034.85 cm-1; MS: (m/z) = 273.2 (M ? 1); Anal. Calc. for C13H21O4P: C,
57.35; H, 7.77; Found: C, 57.40; H, 7.81.
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Ultrasound assisted green synthesis of a…
Dimethyl (hydroxy(4-methylphenyl)methyl)phosphonate (13a, C10H15O5P)
White powder; 87 % yield; 31P NMR (100 MHz, CDCl3): d = 21.20 ppm; 1H
NMR (250 MHz, CDCl3): d = 2.35 (s, 3H, CH3-CAr), 3.63 (d, J = 9.05 Hz,
3H,CH3-O), 3.74 (d, J = 10.64 Hz, 3H, CH3-O), 5.01 (d, J = 14.78 Hz, 1H, CH*),
7.10–7.48 (m, 4H, H-Ar) ppm; 13C NMR (75 MHz, CDCl3): d = 25.13, 54.06,
54.59, 72.15, 73.50, 116.52, 121.64, 127.80, 129.90, 132.56 ppm; IR (KBr):
m = 3254.00, 1474.13, 1255.83, 1031.07 cm-1; MS: (m/z) = 231.1 (M ? 1); Anal.
Calc. for C10H15O5P: C, 52.18; H, 6.57; Found: C, 52.24; H, 6.62.
Dimethyl (3-hydroxy-2-oxoindolin-3-yl)phosphonate (1b, C10H12NO5P)
Color powder; 85 % yield; 31P NMR (100 MHz, CDCl3): d = 19.98 ppm; 1H NMR
(250 MHz, CDCl3): d = 3.73 (d, J = 7.32 Hz, 3H,CH3-O), 3.81 (d, J = 9.45 Hz,
3H, CH3-O), 7.13–7.23 (m, 2H, H-Ar), 7.26–7.35 (m, 2H, H-Ar) ppm; 13C NMR
(75 MHz, CDCl3): d = 54.22, 55.36, 108.10, 118.70, 119.23, 120.40, 128.55,
129.64, 134.15, 158.25 ppm; IR (KBr): m = 3321.20, 3180.63, 1690.34,
1237.75 cm-1; MS: (m/z) = 258 (M ? 1); Anal. Calc. for C10H12NO5P: C,
46.70; H, 4.70; N, 5.45; Found: C, 46.78; H, 4.75; N, 5.50.
Dimethyl (1-hydroxy-1-phenylethyl)phosphonate (2c, C10H15O4P)
Oil; 84 % yield; 31P NMR (100 MHz, CDCl3): d = 22.15 ppm; 1H NMR
(250 MHz, CDCl3): d = 1.64 (s, 3H, CH3-C), 3.63 (d, J = 8.40 Hz, 3H,CH3-O),
3.96 (d, J = 9.14 Hz, 3H, CH3-O), 7.15–7.40 (m, 5H, H-Ar) ppm; 13C NMR
(75 MHz, CDCl3): d = 15.20, 54.40, 55.25, 101.02, 119.10, 122.58, 128.57,
129.71, ppm; IR (KBr): m = 3315.05, 1510.21, 1251.08, 1025.20 cm-1; MS: (m/
z) = 231 (M ? 1); Anal. Calc. for C10H15O4P: C, 58.18; H, 6.57; Found: C, 58.14;
H, 6.59.
Results and discussion
As part of our research program focused towards the development of highly opportune
methods for the synthesis of diverse phosphonate derivatives [39–44], we have
developed a simple and very efficient method for the preparation of a-hydroxyphos-
phonates under green chemical conditions.
We report here the application of ultrasound irradiation in the synthesis of
a-hydroxyphosphonates under catalyst-free and solvent-free conditions. This reaction
involves the condensation of aromatic aldehydes or ketones and trialkylphosphite.
The process was promoted by directly immersing of reaction vessels into the
ultrasonic cleaning bath, which provides a fairly even distribution of energy into the
reaction medium. The reaction was completed within 10–37 min, with a substantial
increase in the yield of product. The collapse of cavitation bubbles results in the
formation of very reactive chemical species having short lifetimes, facilitating the
rapid synthesis of a-functionalized phosphonates derivatives. This is an efficient and
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A. Bouzina et al.
Scheme 1 Ultrasound assisted synthesis of a-hydroxyphosphonates from aldehydes
environmentally benign methodology for the synthesis of a-hydroxyphosphonates at
ambient temperature (Scheme 1).
The results are summarized in (Table 1, Entry 1a–13a). This is an efficient and
eco-sustainable methodology for the synthesis of a-hydroxyphosphonates at
ambient temperatures. The reaction is easily scalable and products are obtained in
excellent yields.
For the resulting compounds, IR spectra showed a band at 1220–1260 cm-1
(P=O) of phosphonate moiety, and a band at 3250–3350 cm-1 (OH) of hydroxyl
group. In 1H-NMR spectra, the structure of a-hydroxyphosphonates was confirmed
by a signal at 5.0–5.2 ppm, corresponding to *CH.
To explore the scope and limitations of this procedure, we extended our study of
isatin derivative. The isolated yields of products (Table 2, Entry 1b–2b) were in the
range of 85–86 % after 35–37 min of reaction (Scheme 2).
Encouraged by the preliminary results and to increase the scope of this reaction,
we examined this method to ketones (Scheme 3). The reaction gave good yields
Scheme 2 Ultrasound assisted synthesis of a-hydroxyphosphonates from isatin
Scheme 3 Ultrasound assisted synthesis of a-hydroxyphosphonates from ketones
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Ultrasound assisted green synthesis of a…
(84–85 %) after (25–35 min). The results are summarized in (Table 3, Entry
1c–3c).
The structures of the synthesized compounds are confirmed by elemental analysis
1
as well as by IR and H, 13C, 31P NMR spectral data and MS.
Conclusions
In conclusion, a green, efficient, and environmentally benign methodology towards
the synthesis of a-hydroxyphosponate has been reported. a-hydroxyphosphonates
were synthesized by the addition of trialkylphosphite to a variety of arylaldehydes
or ketone under neat conditions by simple grinding process; this has proven to be an
excellent method. The effect of ultrasound has mostly been shown by the increasing
yields of reactions, and in some cases, the ratio of formed products.
Acknowledgments This work was supported financially by The General Directorate for Scientific
Research and Technological Development (DG-RSDT), Algerian Ministry of Scientific Research,
Applied Organic Chemistry Laboratory (FNR 2000). We also thank Pr. Jacques Lebreton from the
University of Nantes and Dr. Zouhair Bouaziz and Pr. Marc Le Borgne from the University Claude
Bernard Lyon for their help in the identification for all products in NMR and MS.
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