Transamidation of primary carboxamides, phthalimide, urea and thiourea with amines using Fe(OH)3@Fe3O4 magnetic nanoparticles as an efficient recyclable catalyst

Article abstract of DOI:10.1039/c5ra27680b

The highly efficient transamidation of primary amides, phthalimide, urea and thiourea with amines catalyzed by magnetic Fe(OH)₃@Fe₃O₄ nanoparticles is described. This magnetic nanocomposite is able to catalyze transamidation reactions of a wide range of the above-mentioned substrates with amines, generating a new amide bond in moderate to good yields. The catalyst exhibited very good recyclability and reusability up to five runs without significant loss of its catalytic activity.

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Transamidation of primary carboxamides, phthalimide, urea and
thiourea with amines using Fe(OH)3@Fe3O4 magnetic
nanoparticles as an efficient recyclable catalyst†
Received 00th January 20xx,
Accepted 00th January 20xx
Marzban Arefi and Akbar Heydari*
DOI: 10.1039/x0xx00000x
The highly efficient transamidation of primary amides, phthalimide, urea and thiourea with amines catalyzed by magnetic
Fe(OH)3@Fe3O4 nanoparticles is described. This magnetic nanocomposite is able to catalyze transamidation reaction of
wide range of above-mentioned substrates with amines, generating new amide bond in moderate to good yields. The
catalyst exhibited very good recyclability and reusability up to five runs without significant loss of its catalytic activity.
www.rsc.org/
economy and possess potential environmental problems due
to produce a significant amount of waste.
Recently, heterogeneous catalysts such as CeO2,11 Fe3+-
Introduction
The amide bond formation is an important functional group in
chemistry and nature due to its presence in polymers, dyes,
peptides, and protein structures.1 Consequently, the
construction of amide bonds has been one of the most studied
transformation in organic synthesis. Conventional way to make
an amide bond involves the use of either carboxylic acid (or
derivatives) or coupling reagents in stoichiometric quantities,2
resulting in poor atom-efficiency and formation of a significant
amount of chemical waste. To circumvent these drawbacks,
numerous alternative amide formation protocols have been
explored.3 Among them, transamidation of amides with
amines is potentially an attractive alternative method for
exchanging the constituents of two different amide groups.
Due to the high reaction temperatures required to break the
amide bond, transamidation under thermal conditions4 is
considered as an unfavorable method for amide formation.
Alternatively, enzyme mediated transamidation reactions have
been reported,5 whereas they have limited scope and require
development of task specific enzyme as well as long reaction
time. In order to overcome these drawbacks, new
homogeneous and heterogeneous catalysts have recently
been reported.
exchanged montmorillonite (Fe-mont),12 mesoporous niobium
oxide spheres (MNOS)13 and sulfated tungstate14 have been
deployed in transamidation reactions.
Although, these heterogeneous-catalytic systems for
transamidation, promote the drawbacks existing with the
homogeneous-catalytic systems, the efficiency and easy
separation of the product and catalysts from the reaction
mixture can be challenging in these catalytic methodologies.
Due to the high stability and easy separation of the catalyst
from the reaction mixture by using an external magnet,
magnetic nanoparticles-supported catalysts have been
successfully deployed in
a variety of important organic
reactions.15 As part of our continuing interests in using
magnetic nanoparticles as catalyst support in organic
reactions, we have recently reported the results obtained for
the tandem oxidative amidation of alcohols with amine
hydrochloride salts using superparamagnetic Fe(OH)3@Fe3O4
nanoparticles catalyst.16 To further establish other organic
transformations with our catalyst, herein, we describe an
inexpensive, magnetically recoverable and environmentally
friendly catalytic system (Fe(OH)3@Fe3O4) for the
transamidation of primary carboxamides, phthalimide, urea
and thiourea with amines (Scheme 1).
Stahl,6 Myers,7 Beller,8 Williams,9 and other groups10
reported elegant methods for transamidation by employing
homogeneous catalytic systems. Yet, despite the advances
achieved, these homogeneous catalysts suffer from difficulty
in recovery and recycling of the catalyst, resulting in poor atom
Chemistry Department, Tarbiat Modares University, P.O. Box 14155-4838, Tehran,
Iran. E-mail: heydar_a@modares.ac.ir; Fax: (+98)-21-82883455; Tel: (+98)-21-
82883444
†
Electronic
DOI: 10.1039/x0xx00000x
Supplementary
Information
(ESI)
available:
See
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Scheme 1. Fe(OH)3@Fe3O4 catalyzed transamidation of
primary carboxamides, phthalimide, urea and thiourea with
amines.
Figure 1. XRD pattern of Fe3O4 and Fe(OH)3@Fe3O4.
Results and discussion
As can be seen in Scheme 2, the Fe(OH)3@Fe3O4 catalyst was
prepared through
a simple pathway (for details see
Experimental section).
Scheme 2. Preparation of Magnetic Fe(OH)3@Fe3O4 Nanoparticles.
The prepared catalyst was characterized using some
instrumental techniques, such as XRD, SEM, TEM, TGA, and
VSM. The XRD pattern of this catalyst is shown in Figure 1. In
particular, seven characteristic peaks at 2θ equal 21.5°, 35.4°,
41.7°, 50.9°, 63.7°, 68.0°, and 75.1°, which correspond to the
Miller indices values {hkl} of {111}, {220}, {311}, {400}, {422},
{511}, and {440}, respectively. The XRD pattern resembles that
of Fe3O4 nanoparticles and no signal is observed from the
Fe(OH)3 phase, indicating that the Fe(OH)3 compound is
amorphous. Nanoparticles morphology was evaluated by TEM
(Figure 2) and SEM (Figure 3) images. Core−shell structure and
spherical in shape with a smooth surface morphology of the
particles are clearly seen in these images. On the other hand,
the particle size distribution, obtained from the generated
histogram using TEM image, revealed the Fe(OH)3@Fe3O4
MNPs with a mean size of 18 nm (Figure 4). TGA recorded
under nitrogen atmosphere for Fe3O4 (Figure 5A) and
Fe(OH)3@Fe3O4 MNPs (Figure 5B) determining this catalyst
consisting 9.4 wt% of Fe(OH)3 and 90.6 wt % of Fe3O4. The
magnetic feature of the catalyst was confirmed by vibrating
sample magnetometry (VSM). Magnetizing (emu/g) as a
function of applied field (Oe) is depicted in Figure 6. The
magnetization curve demonstrates that these Fe(OH)3@Fe3O4
nanoparticles (Possessed magnetic saturation(Ms) about 40.0
emu/g) have superparamagnetic properties which accounts for
easy recovery of this catalyst.
Figure 2. TEM image of the catalyst.
Figure 3. SEM image of the catalyst.
2 | J. Name., 2012, 00, 1-3
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product, N-benzylformamide 3a, was formed in just 16% yield
(Table 1, entry 1). To increase the yield of the product, a series
of experiments were carried out to screen the effect of various
reaction parameters and these results are summarized in Table
1. Screening organic solvents (CH3CN, Toluene, p-xylene, THF,
EtOH, and DMSO) indicated that p-xylene is the best (Table 1,
entries 1-7). Further study showed that the catalyst is essential
for this transamidation reaction. In the absence of the catalyst,
transamidation did not happen (Table 1, entry 8). Finally, the
effect of catalyst loading on efficiency was studied and 30 mg
per 1.0 mmol of benzylamine was the best (Table 1, entries 9-
11). Furthermore, the low efficiency of the reaction in the
presence of Fe3O4 nanoparticles showed that iron (III)
hydroxides, coated on the magnetic nanoparticles, plays a
major role as catalyst (Table 1, entry 12). Therefore, the
optimum conditions were obtained when we performed the
reaction by using 30 mg of Fe(OH)3@Fe3O4 at 135 °C with the
respective p-xylene as the solvent (Table 1, entry 4).
Figure 4. Histograms generated from the sizes of the catalyst using
the TEM images.
Table 1. Optimization of the reaction conditions.a
Entry
1
Cat. (mg)
30
Solvent
H2O
Yield (%)b
16
2
30
CH3CN
toluene
p-xylene
THF
58
3
30
81
4
30
92
5
30
53
6
30
EtOH
66
7
30
DMSOc
p-xylene
p-xylene
p-xylene
p-xylene
p-xylene
28
8
---
---
9
20
68
Figure 5. TGA results of Fe3O4 and Fe(OH)3@Fe3O4.
10
11
12
25
74
35
30d
92
31
aReaction conditions: Benzylamine (1.0 mmol), Formamide (1.0
b
mmol), solvent (1.0 mL) under Ar atmosphere, 10 h. Yield of
the isolated product is based on the amine. cReaction
performed at 140 °C. d30 mg of Fe3O4 nanoparticles were used.
The above optimized catalytic system was extended to the
transamidation reaction. So, a wide range of amines with
amides, urea, thiourea and phthalimide were subjected to the
reaction conditions and the corresponding transamidation
products were obtained in moderate to good yields (Table 2).
Subsequently, we have applied the optimized reaction
conditions for different amides, where acetamide, formamide,
and N,N-dimethylformamide could be successfully converted
to the corresponding products when reacted with different
amines.
Figure 6. Magnetization curve of Fe3O4 and the catalyst.
Transamidation of benzylamine with formamide using
Fe(OH)3@Fe3O4 magnetic nanoparticles as catalyst was chosen
as
a model reaction under the following conditions:
benzylamine 1a (1.0 mmol), formamide 2a (1.0 mmol), H2O
(1.0 mL), under Ar atmosphere at reflux conditions.
Unfortunately, after 10 h of reaction time, the corresponding
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Table 2. Fe3O4@Fe(OH)3 catalyzed transamidation of primary amine
amides, phthalimide, urea and thiourea with amines.a,b
2 to the amide (Scheme 2, intermediate (II)).
Subsequently, this generated intermediate can undergo
reversible proton exchange to form intermediate (III). Finally,
the catalytic cycle ends with removal of amine
3 and the
dissociation of amide 4 from Fe(OH)3@Fe3O4 catalyst.
O
H
O
H
N
H
N
H
N
H
Ph
N
H
H
O
H
O
3a, 92% (87%)
3b, 88% (81%)
3c, 82% (80%)
3d, 91% (84%)
F
H
H
H
N
H
N
N
H
N
H
H
H
O
O
O
O
O
Br
O2N
3e, 89% (88%)
O
3f, 80% (75%)
3g, 78% (72%)
O
3h, <10%
H
N
H
N
N
H
Ph
N
H
O
O
3i, 87%
3k, 67%
3j, 70%
3l, 77%
H
H
H
N
H
N
N
N
O
O
3n, 64%
O
O
Br
3m, 79%
3o, 64% C
H
H
O
O
N
N
Ph
N
N
Ph
Ph
N
N
Ph
O
H
H
H
H
C
C
C
3p, 71%
3q, 85%
S
3r, 82%
H
N
H
N
H
N
H
N
Scheme 2. Proposed mechanism for the Fe(OH)3@Fe3O4
Ph
N
N
Ph
H
H
S
O
C
catalyzed transamidation reaction.
O
O
O
O
3t, 49% C
3u, 54% C
3s, 58%
O
O
O
S
After establishing the activity and versatility of the
Fe(OH)3@Fe3O4 catalyst for transamidation, its recyclability
was examined in the preparation of compound 3a under the
optimized reaction conditions. For this, after completion of the
reaction, the catalyst was easily removed from the reaction
mixture by using an external magnet, washed with ethanol,
dried at ambient temperature and subjected for the next cycle.
The Fe(OH)3@Fe3O4 catalyst could be reused up to five cycles
without any significant loss of its catalytic activity (Figure 7).
Ph
Ph
N
N
N
Ph
N
N
H
H
Ph
C
3v, 58%
3w, 70%
3x, 52%
3y, 68%
O
O
O
aReaction conditions: amine (1.0 mmol), amide (1.0 mmol), p-
xylene (1.0 mL) under Ar atmosphere, 10 h. bIsolated yields;
the yields of the transamidation of N,N-dimethylformamide
with amines are given in parentheses. cAmine (2.0 mmol),
amide (1.0 mmol).
Generally speaking, anilines bearing electron-donating
groups such as methyl or methoxy, were better than those
which bearing electron with-drawing groups, such as fluoro,
bromo, or nitro (Table 2, 3d, 3e vs 3f-h). Worthy of note is that
transamidation of formamide or N,N-dimethylformamide with
amines gave the corresponding N-formylated products in
excellent yields (Table 2, entries 3a-g). To further extend the
scope of this methodology, the Fe(OH)3@Fe3O4 catalyzed
transamidations of urea and thiourea were examined with
amines and the corresponding target products obtained in
moderate to good yields (Table 2, entries 3o-v). Finally, our
study was focused on the transamidation of phthalimide with
several primary amines such as aniline, benzylamine, and 4-
methylaniline and the corresponding N-substituted
phthalimides were obtained in good yields (Table 2, entries
Figure 7. Recyclability study of the catalyst in the preparation
of compound 3a
.
3w-y).
10a, 17
Based on the results and literature reports,6d,
we
To compare the efficiency of the Fe(OH)3@Fe3O4 catalyst with
the previously reported ones, we have tabulated the
corresponding data for promotion of N-benzylformamide
(product 3a) (Table 3). It is obvious that our catalyst worked
remarkably well to give the desired product in 92% yield in
shorter reaction time.
propose a plausible mechanism for this transformation as
shown in Scheme 2. In proposed mechanism, Fe(OH)3 shell
played a double role: (i) hydrogen bond donor by H-bonds
formation with the nitrogen atom of amide 1: (ii) lewis acid at
the iron atom by coordination to the oxygen atom of the
amide. This double activation would be followed by addition of
4 | J. Name., 2012, 00, 1-3
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Table 3. Comparison of different catalysts in the formation of N-
benzylformamide.
Conclusions
Entry
Catalyst
Condition
Time
(h)
30
36
16
16
36
10
Yield
(%)
93
83
81
86
94
92
Ref.
In conclusion we have demonstrated an environment friendly,
inexpensive and magnetically separable Fe(OH)3@Fe3O4
catalytic system for transamidation. This catalyst exhibited
high catalytic activity for transamidation of amines with
amides, urea, thiourea and phthalimide. By using this catalytic
system, all corresponding target products were obtained in
moderate to good yields. Due to its straightforward
preparation, facial separation from the reaction medium and
recyclability, the Fe(OH)3@Fe3O4 catalytic system described
18
19
1
2
3
4
5
6
Fe(NO3)3.9H2O
Chitosan
B(OH)3
H2NOH.HCl
L-Proline
Toluene/reflux
Neat/150 °C
H2O/100 °C
Toluene/reflux
Neat/150 °C
p-xylene/reflux
10a
9a
20
Fe(OH)3@Fe3O4
---
Experimental
here, represents
reported protocols.
a good compliment to the previously
All experiments were carried out under argon. All chemicals
and solvents were purchased from commercial suppliers and
used without further purification. FT-IR spectra were obtained
over the region 400−4000 cm−1 with a Nicolet IR100 FT-IR with
Acknowledgements
spectroscopic grade KBr. H NMR and 13C NMR spectra were
1
We acknowledge Tarbiat Modares University for partial
support of this work.
recorded on a Bruker Avance (DRX 400 MHz and DRX 500 MHz)
in pure deuterated CDCl3, and DMSO-d6 solvents with
tetramethylsilane (TMS) as internal standard.
Notes and references
Preparation of Fe(OH)3@Fe3O4 Catalyst. The synthesis of the
Fe(OH)3@Fe3O4 catalyst was conducted according to the
procedure previously reported.16 In a typical preparation
procedure, the mixture of FeCl3·6H2O (4.0 mmol) and
FeCl2·4H2O (2.0 mmol) salts in deionized water (40.0 mL) was
placed in a two-necked flask under vigorous stirring. An
ammonia solution (25% (w/w)) was added in dropwise manner
over 5 min to the stirring mixture to maintain the reaction pH
about 11. The resulting black dispersion was stirred vigorously
for 1h at room temperature and then was refluxed for 1h.
Fe3O4 nanoparticles were magnetically gathered and the
residue was repeatedly washed with water and ethanol.
Subsequently, as-prepared Fe3O4 nanoparticles and 15.0 mmol
of FeCl3·6H2O were ultrasonically dispersed into 10.0 mL of
ethanol. After totally dissolution and dispersion, the
nanoparticles were separated from the ethanol solution by
magnetic decantation and dried at 80 °C for 4h.
Fe(OH)3@Fe3O4 nanoparticles were obtained by dropwise
addition of aqueous ammonia (25% (w/w), 5 mL) to the dried
brown nanoparticles under vigorous stirring. Finally, the
products of Fe(OH)3@Fe3O4 were magnetically separated,
washed with water, and dried in an oven at 373 K overnight for
further usage.
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General Procedure for the synthesis of products 3a-y. To a
mixture of catalyst (30.0 mg, 2.6 mol%) and amine (1.0 mmol)
in p-xylene (1.0 mL) was added amide (1.0 mmol) under argon
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removed under vacuum, and the resulting residue was purified
by column chromatography on silica gel to afford the desired
product.
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For Table of Contents Use Only
Transamidation of primary carboxamides, phthalimide, urea and
thiourea with amines using Fe(OH)3@Fe3O4 magnetic
nanoparticles as an efficient recyclable catalyst
Marzban Arefi † and Akbar Heydari †*
O
O
+ H N R
NH
R N
2
O
O
O(S)
O
+
Fe(OH)3@Fe3O4
p-xylene, reflux
10 h
R
R
R1
N
N
H
NH2
H
R2
R3
N
H
(S)
O
O
R2
H2N
NH2
R1
N
+
R3
H2N R
6 | J. Name., 2012, 00, 1-3
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