P-Dodecylbenzenesulfonic acid: A highly efficient catalyst for one-pot synthesis of α-aminophosphonates in aqueous media

Article abstract of DOI:10.1002/hc.21079

A highly efficient one-pot three-component reaction of aldehydes or ketones, amines, and trimethyl or triethyl phosphite catalyzed by p-dodecylbenzensulfonic acid is developed for the synthesis of α-aminophosphonates at room temperature in water.

Full text of DOI:10.1002/hc.21079

Heteroatom Chemistry
Volume 24, Number 3, 2013
P-Dodecylbenzenesulfonic Acid: A Highly
Efficient Catalyst for One-Pot Synthesis of
α-Aminophosphonates in Aqueous Media
Barahman Movassagh and Saba Alapour
Department of Chemistry, K. N. Toosi University of Technology, Tehran, Iran
Received 30 September 2012; revised 12 January 2013
well documented. In addition, in agrochemistry, a
ABSTRACT:
A highly efficient one-pot three-
number of α-aminophosphonates are used as fungi-
cidal [8], insecticidal [9], and herbicidal agents [10].
The usual synthesis of α-aminophosphonates,
the Kabachnik–Fields reaction, involves the nucle-
ophilic addition of phosphites to imines catalyzed
by Brønsted [11] or Lewis acids such as MgBr2
[12a], ZnCl2 [12a], BF3.OEt2 [12b,c], and SnCl4
[12b], etc. or by bases [13]. However, these meth-
ods have limitations, as many imines are mois-
ture sensitive and not stable enough for isolation.
Recently, one-pot three-component preparation has
been reported in organic solvents using BiCl3 [14],
SbCl3/Al2O3 [15], Cu(OTf)2 [16], InCl3 [17], ZrCl4
[18], GaI3 [19], In(OTf)3/MgSO4 [20], silica sulfu-
ric acid [21], Amberlyst-15 [22], and H-beta zeolite
[23]. More recently, methods employing ionic liq-
uids [24], water [25], neat conditions [26], as well
as microwave irradiation [27], and ultrasonic irradi-
ation [28] have been introduced. However, various
drawbacks, such as synthetic inconvenience, a long
reaction time, use of expensive or toxic reagents,
and a costly and moisture-sensitive catalyst, etc. en-
countered in the reported methodologies necessitate
the development of a more efficient and convenient
method.
component reaction of aldehydes or ketones, amines,
and trimethyl or triethyl phosphite catalyzed by
p-dodecylbenzensulfonic acid is developed for the syn-
thesis of α-aminophosphonates at room temperature
in water. 2013 Wiley Periodicals, Inc. Heteroatom
Chem. 24:174–178, 2013; View this article online at
wileyonlinelibrary.com. DOI 10.1002/hc.21079
ꢀC
INTRODUCTION
Multicomponent reactions constitute an especially
attractive synthetic strategy in which three or more
different starting materials react to a final product
in a one-pot procedure. Moreover, they are powerful
tools in the modern drug discovery process and allow
the rapid, automated, and high-throughput genera-
tion of organic compounds, by constructing several
new bonds in one pot [1].
The organic chemistry of phosphorus is a
wide and exciting field, with great opportunities
for research or applications development. The α-
aminophosphonates, amino acid analogues, have at-
tracted considerable attention during the past two
decades because of their wide range of biological and
medicinal properties [2]. The potential of α-amino
phosphonates as anti-HIV [3], antibiotic [4], anti-
cancer [5], antitumor [6], and antiviral agents [7] is
The organic reactions in aqueous media have
attracted considerable attention in recent years,
since they offer a powerful tool for minimizing
waste production and harmful organic solvent dis-
posal [29]. However, water is usually avoided as a
medium for organic reactions, because of the in-
solubility, and occasionally decomposition or de-
activation of many reactive substrates, reagents,
and catalysts by this solvent [30]. Surfactants are
Correspondence to: B. Movassagh; e-mail: bmovass1178@
yahoo.com
Contract grant sponsor: K. N. Toosi University of Technology
Research Council.
ꢀC
2013 Wiley Periodicals, Inc.
174

p-Dodecylbenzenesulfonic Acid Catalyst for Synthesis of Aminophosphonates 175
TABLE 1 Optimization of Reaction Conditions
ous aldehydes (aromatic, heteroatomatic, aliphatic)
or ketones (dialkyl, cyclic, aryl alkyl), amines
NHPh
(aromatic, aralkyl, cycloalkyl), and trimethyl- and
triethyl phosphite (Table 2). Although complete
conversions and high isolated yields were gener-
ally obtained for the reactions between a vari-
ety of aromatic/heteroaromatic/aliphatic aldehydes
with aromatic amines, the reaction of an aromatic
aldehyde (benzaldehyde) with cyclohexylamine was
slow with poor yield of the corresponding prod-
uct (Table 2, entry 11). The same observation was
found for cyclohexanone; while this ketone reacted
smoothly with aniline, affording the corresponding
α-aminophosphonate in high yield (Table 2, entry
26), its reaction with benzylamine took longer time
with very low yield (Table 2, entry 25). The reac-
tion of acetophenone with aniline resulted in poor
yield of the corresponding product (Table 2, entry
27) even after 14 h. Unfortunately, the reaction of
the conjugated aldehyde (cinamaldehyde) with ani-
line and trimethyl phosphite (Table 2, entry 16)
gave a mixture of products, which was difficult to
separate.
PhCHO + PhNH2
2a
+
P(OMe)3
P(OMe)2
O
Ph
3a
1a
4a
Entry Solvent Catalyst (mol%) Time (h) Yielda (%)
1
2
3
4
5
5
5
5
5
3
2
1
7
2
6
3
80
82
86
78
85
90
87
79
64
73
67
CH3CN
EtOH
CHCl3
H2O
3
5
0.5
1
6
7
H2O
H2O
1
1
1
1
8
9
H2O
H2O
10
11
H2O
H2O
10
15
1
aIsolated yields.
stable in water and can make organic materials
soluble or form colloidal dispersions [31], so they
can overcome the above drawbacks of the reactions
and can be used as good catalysts in water. There
are several reports in which a catalytic amount of
a Lewis acid-surfactant-combined catalyst, such as
scandium tris(dodecyl sulfate) [32a–d] or a Brønsted
acid-surfactant-combined catalyst, such as dodecyl-
benzenesulfunic acid (DBSA) [32e–h], was used.
From the mechanistic point of view, we believe
that the role of DBSA is to promote the formation of
an imine and to convert the same by protonation of
the more electrophilic iminium ion intermediate, to
facilitate the attack of the phosphite nucleophile.
CONCLUSIONS
RESULTS AND DISCUSSION
In conclusion, the new procedure described here ap-
pears to be highly competitive with other methods
reported in the literature and in some cases better
results are obtained, especially in terms of reaction
time and yields. It should be noted that these high
yields are obtained in water at room temperature
and high reaction rates. This process represents a
suitable option to existing methods.
Our continued interest in the development of
ecofriendly and green processes using water as a
solvent [33] prompted us to develop a highly sim-
ple, alternative procedure for the synthesis of α-
aminophosphonates by a one-pot three-component
reaction of an aldehyde/ketone, amine, and tri-
ethyl (trimethyl) phosphite utilizing DBSA in water
(Scheme 1).
To optimize the reaction conditions, the reac-
tion of benzaldehyde (1.0 mmol), aniline (1.0 mmol),
and trimethyl phosphite (1.2 mmol) was studied in
various conditions at room temperature (Table 1).
The best reaction condition resulted when DBSA
(3 mol%) in water was used at room temperature.
On the basis of the above findings, we further
desired to study the general reactivities of vari-
EXPERIMENTAL
General
1H and 13C NMR spectra were recorded with a
Bruker Avance AQS-300 spectrometer (Germany),
with CDCl3 as a solvent and the chemical shifts
are determined with reference to residual CHCl3
in CDCl3. DBSA, aldehydes, ketones, amines, and
dialkyl phosphites were purchased from Merck
(Germany) and Acros (France) companies and used
without further purification. Melting points were
recorded on a Bu¨chi B-540 (Switzerland) appara-
tus and are uncorrected. IR spectra were obtained
using an ABB FTLA 2000 instrument. MS was car-
ried out on a Hewlett–Packard 5973 (United States)
NHR3
O
O
DBSA (3 mol%)
+
R3NH2
+
P(OR4)3
P
H2O, r.t.
R2
OR4
R2
R1
R1
OR4
4
2
3
1
SCHEME 1 Kabachnik–Fields reaction using DBSA as a
catalyst in water.
Heteroatom Chemistry DOI 10.1002/hc

176 Movassagh and Alapour
TABLE 2 DBSA-Catalyzed Synthesis of α-Aminophosphonates from Various Aldehydes/Ketones, Amines, and Phosphites in
Water
Entry
Carbonyl Compound
R3
R4
Product
Time (min)
Yielda,b (%)
1
2
3
4
5
6
7
8
Benzaldehyde
2-Chlorobenzaldehyde
2,4-Dichlorobenzaldehyde
p-Anisaldehyde
Ph
Ph
Ph
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Et
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
4m
4n
4o
4p
4q
4r
30
20
7
5
45
10
45
20
180
30
720
60
120
240
30
40
150
50
8
45
120
40
60
90 [26]c
95 [21]
92 [21]
83 [26]c
C [26]c
96 [34]
90
4-NO2C6H4
Ph
Furfural
2-Naphthaldehyde
Thiophene-2-carbaldehyde
3-Nitrobenzaldehyde
p-Anisaldehyde
Isobutyraldehyde
Benzaldehyde
Cyclohexane carbaldehyde
p-Anisaldehyde
Salicylaldehyde
Thiophene-2-carbaldehyde
Cinnamaldehyde
2-Pyridinecarbaldehyde
4-Hydroxybenzaldehyde
Benzaldehyde
Ph
Ph
Ph
Ph
80 [35]
86 [26]c
86 [26]c
38 [27]c
92 [14]
82 [26]c
95 [14]
83 [26]c
C [26]c
64 [26]c
98 [26]c
96 [27]c
90 [35]
87 [27]c
93
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
Ph
c-C6H11
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Et
Et
Et
Me
Me
Me
Me
Me
Me
Me
Me
Et
4-ClC6H4
Ph
4-MeC6H4
Ph
Ph
Ph
PhCH2
Ph
Ph
4s
4t
p-Tolualdehyde
Benzaldehyde
N-(4-Formylphenyl) acetamide
p-Anisaldehyde
4u
4v
4w
4x
4y
4z
4aa
78 [26]c
93 [26]c
20 [26]c
88 [26]c
21 [26]c
Benzaldehyde
Cyclohexanone
Cyclohexanone
Acetophenone
90
Me
Me
Me
720
120
840
aIsolated yields.
bReferences are given for known compounds.
cA mixture of products was obtained.
spectrometer (EI, 70 eV). All compounds were char-
acterized by comparing their physical data with
those in the literature.
ther purification needed), mp 144◦C; IR (KBr): v
3307, 3024, 2947, 1607, 1504, 1237, 1062, 1027
cm−1
;
1H NMR (300 MHz, CDCl3): δ 3.17 (d, J =
10.5 Hz, 3H), 3.84 (d, J = 10.7 Hz, 3H), 5.19 (br
1
s, 1H), 5.72 (d, JP-H = 24.1 Hz, 1H), 6.59 (d,
General Procedure for Preparation of
DBSA-Catalyzed Synthesis of
α-Aminophosphonates
J = 7.8 Hz, 2H), 6.68 (t, J = 7.3 Hz, 1H), 7.06
(t, J = 7.4 Hz, 2H), 7.43–7.93 (m, 6H), 8.27 (d,
J = 8.5 Hz, 1H); 13C NMR (proton decoupled, 75
1
MHz, CDCl3): δ 51.1 (d, JP-C = 152.0 Hz, CH),
To a solution of DBSA (0.09 mmol, 3 mol%) in H2O
(15 mL), an amine (3 mmol), an aldehyde or ketone
(3 mmol), and dialkyl phosphite (3.6 mmol) were
added successively at 25◦C. After stirring at room
temperature for the period of time listed in Table
2, a saturated aqueous NaHCO3 solution (20 mL)
and brine (20 mL) were added, the mixture was ex-
tracted with EtOAc (25 mL), and the organic layer
was dried over anhydrous Na2SO4. The solvent was
evaporated under reduced pressure, and the crude
product was purified either by recrystallization or
by preparative TLC (silica gel). Spectral data for se-
lected products is presented below.
2
2
53.74 (d, JP-C = 6.8 Hz, OCH3), 53.76 (d, JP-C
=
6.7 Hz, OCH3), 113.64, 118.46, 122.64, 125.57,
125.65, 125.68, 125.76 (d, 3JP-C = 5.4 Hz, CH), 126.56,
128.70 (d, 3JP-C = 3.5 Hz, CH), 129.15, 129.26, 131.45,
133.88, 146.12 (d, 2JP-C = 14.2 Hz, C).
Dimethyl (3-nitrophenyl)(N-phenylamino) meth-
ylphosphonate (4h) [35]. Yellow crystals (EtOAc/n–
hexane), mp 131◦C; IR (KBr): v 3301, 3106, 2940,
1602, 1533, 1024 cm−1
;
1H NMR (300 MHz,
CDCl3): δ 3.62 (d, J = 10.7 Hz, 3H), 3.81 (d,
J = 10.7 Hz, 3H), 4.96 (d, 1JP-H = 25.0 Hz, 1H), 5.35
(br s, 1H), 6.59 (d, J = 7.8 Hz, 2H), 6.71(t, J = 7.3 Hz,
1H), 7.10 (t, J = 8.4 Hz, 2H), 7.49 (t, J = 7.9 Hz, 1H),
7.85 (d, J = 7.4 Hz, 1H), 8.11 (d, J = 8.1 Hz, 1H),
Dimethyl (2-naphthyl)(N-phenylamino) methyl-
phosphonate (4f) [26c]. White crystals (no fur-
Heteroatom Chemistry DOI 10.1002/hc

p-Dodecylbenzenesulfonic Acid Catalyst for Synthesis of Aminophosphonates 177
8.38 (d, J = 1.9 Hz, 1H); 13C NMR (proton decoupled,
JP-C = 5.5 Hz), 129.14, 146.36 (d, JP-C = 148 Hz),
159.28 (d, JP-C = 3.0 Hz).
2
75 MHz, CDCl3): δ 53.77 (d, JP-C = 6.8 Hz, OCH3),
2
1
54.26 (d, JP-C = 6.9 Hz, OCH3), 55.06 (d, JP-C
=
=
3
Dimethyl (4-methylphenyl)(N-phenylamino) me-
thylphosphonate (4t) [24e]. Greenish-white solid
(EtOAc–n-hexane), mp 130◦C; IR (KBr): v 3299,
150.3 Hz, CH), 113.81, 118.99, 122.75 (d, JP-C
5.3 Hz, CH),123.05, 129.33, 129.66, 133.94, 138.67,
145.61 (d, JP-C = 14.1 Hz, C), 148.51 (d, JP-C
2
3
=
1
2951, 2860, 1521, 1456, 1269, 1028 cm−1; H NMR
2.8 Hz, CH).
(300 MHz, CDCl3): δ 2.31 (s, 3H), 3.49 (d, J = 10.5 Hz,
1
3H), 3.76 (d, J = 10.6 Hz, 3H), 4.81 (d, JP-H
=
Dimethyl 2-methyl-1-(N-phenylamino) propyl-
phosphonate (4j) [26c]. Fade white solid (prep.
TLC, n-hexane–EtOAc, 4:1), mp 97◦C; IR (KBr): v
24.2 Hz, 1H), 4.86 (br s, 1H, NH), 6.62–6.72 (m,
3H), 7.08–7.16 (m, 4H), 7.39 (d, J = 6.8 Hz, 2H); 13C
NMR (proton decoupled, 75 MHz, CDCl3): δ 21.15,
53.72, 53.81, 55.35 (d, 1JP-C = 151.1 Hz, CH), 113.92,
118.43, 127.76 (d, JP-C = 5.6 Hz), 129.18, 129.46 (d,
JP-C = 2.6 Hz) 132.56 (d, JP-C = 2.5 Hz), 137.73 (d,
JP-C = 3.3 Hz), 146.28 (d, JP-C = 14.7 Hz).
3344, 2962, 1602, 1497, 1327, 1286, 1239, 1023 cm−1
;
1H NMR (300 MHz, CDCl3): δ 1.04 (d, J = 7.1 Hz, 3H),
1.07 (d, J = 7.1 Hz, 3H), 2.17–2.29 (m, 1H), 3.60–3.73
(m, 7H), 3.88 (m, CH, 1H), 6.64 (d, J = 8.0 Hz, 2H),
6.70 (t, J = 7.2 Hz, 1H), 7.16 (t, J = 8.4 Hz, 2H); 13C
NMR (proton decoupled, 75 MHz, CDCl3): δ 18.05 (d,
3JP-C = 4.7 Hz, CH3), 20.55 (d, 2JP-C = 12.2 Hz, CH),
29.89 (d, 3JP-C = 5.8 Hz, CH3), 52.34 (d, 2JP-C = 7.5 Hz,
Dimethyl (4-acetamidophenyl)(N-phenylamino)
methylphosphonate (4v). Greenish-white crystals
(EtOH–H2O), mp 181◦C; IR (KBr): v 3332, 3276,
3024, 2957, 1674, 1602, 1525, 1217, 1052, 1021, 749
2
OCH3), 53.34 (d, JP-C = 7.0 Hz, OCH3), 56.01 (d,
1JP-C = 150.7 Hz, CH), 113.19, 117.99,129.34, 147.44.
1
cm−1; H NMR (300 MHz, CDCl3): δ 2.14 (s, 3H),
3.51 (d, J = 10.6 Hz, 3H), 3.76 (d, J = 10.6 Hz, 3H),
4.70–4.83 (m, 2H), 6.58 (d, J = 7.9 Hz, 2H), 6.70 (t,
J = 7.3 Hz, 1H), 7.10 (t, J = 8.0 Hz, 2H), 7.35 (d,
J = 8.4 Hz, 2H), 7.48 (d, J = 8.4 Hz, 2H), 8.21 (s,
1H); 13C NMR (proton decoupled, 75 MHz, CDCl3):
Diethyl cyclohexyl(N-phenylamino) methylphos-
phonate (4l) [14]. Light yellow crystals (no further
purification needed), mp 87◦C; IR (KBr): v 3317,
2991, 2931, 2857, 1601, 1506, 1445, 1221, 1026 cm−1
;
2
δ 24.34, 53.87 (d, JP-C = 5.0 Hz, OCH3), 53.94 (d,
1H NMR (300 MHz, CDCl3): δ 1.07–1.38 (m, 11 H),
1.61–2.03 (m, 6H), 3.57–3.68 (m, 1H), 3.85–4.14 (m,
5H), 6.63 (d, J = 8.2 Hz, 2H), 6.69 (t, J = 7.3 Hz,
1H), 7.15 (t, J = 7.7 Hz, 2H); 13C NMR (proton de-
coupled, 75 MHz, CDCl3): δ 16.38 (d, 3JP-C = 5.6 Hz,
1
2JP-C = 5.1 Hz, OCH3), 54.07 (d, JP-C = 151.9 Hz,
CH), 113.95, 118.69, 120.09, 128.28 (d, JP-C = 5.6 Hz),
129.21, 130.48, 138.40, 145.95 (d, JP-C = 14.5 Hz),
168.98 ppm; Major mass peaks: m/z (%) = 348 (7.4),
279 (14.5), 239 (base peak, 100), 197 (47.7), 167
(43.8), 149 (91), 120 (15.6), 104 (28.9), 77 (32.8),
57 (27.7), 43 (44); Anal. calcd. For C17H21N2O4P
(348.34): C 58.62; H 6.08; N 8.04; found: C 58.87;
H 6.06; N 7.62.
3
CH3), 16.46 (d, JP-C = 5.3 Hz, CH3), 26.00, 26.17,
26.29, 28.27 (d, 3JP-C = 4.5 Hz, CH3), 30.96 (d, 2JP-C
=
=
3
1
11.4 Hz), 39.85 (d, JP-C = 5.6 Hz), 56.01 (d, JP-C
2
150.1 Hz), 61.81(d, JP-C = 7.4 Hz, OCH2), 62.63(d,
2JP-C = 7.1 Hz, OCH2), 113.16, 117.74, 129.26, 147.75
(d, 3JP-C = 5.5 Hz).
Dimethyl (1-phenylaminocyclohexyl) phospho-
nate (4z) [26c]. Brownish white solid (prep. TLC:
n–hexane–EtOAc), mp 80◦C; IR (KBr): v 3337, 2934,
Diethyl(4-methoxyphenyl)(N-phenylamino) meth-
ylphosphonate (4m) [26c]. White solid (prep. TLC,
n-hexane–EtOAc, 4:1), mp 106◦C; IR (KBr): v 3294,
1
2855, 1600, 1498, 1449, 1230, 1028 cm−1; H NMR
(300 MHz, CDCl3): δ 1.21–1.85 (m, 10H), 3.67 (d,
J = 10.2 Hz, 6H), 6.81 (t, J = 7.2 Hz, 1H), 7.02
(d, J = 8.2 Hz, 2H), 7.17 (t, J = 7.3 Hz, 2H); 13C
NMR (proton decoupled, 75 MHz, CDCl3): δ 19.94
1
2984, 1601,1509, 1310, 1233, 1021 cm−1; H NMR
(300 MHz, CDCl3): δ 1.14 (t, J = 7.04 Hz, 3H), 1.28
(t, J = 7.05 Hz, 3H), 3.66–3.74 (m, 1H), 3.76 (s, 3H),
3.91–3.99 (m, 1H), 4.04–4.18 (m, 2H), 4.67–4.82 (m,
2H), 6.59 (d, J = 8.0 Hz, 2H), 6.68 (t, J = 7.3 Hz, 1H),
6.86 (d, J = 8.5 Hz, 2H), 7.10 (t, J = 7.8 Hz, 2H), 7.39
(d, J = 8.6 Hz, 2H); 13C NMR (proton decoupled,
2
2
(d, JP-C = 11.1 Hz), 25.28, 30.27, 53.08 (d, JP-C
=
1
7.5 Hz, OCH3), 57.46 (d, JP-C = 159.7 Hz), 118.40,
119.52, 128.83, 145.65.
3
75 MHz, CDCl3): δ = 16.28 (d, JP-C = 5.7 Hz, CH3),
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Heteroatom Chemistry DOI 10.1002/hc