Fe3O4-nanoparticles catalyzed an efficient synthesis of nitriles from aldehydes

Article abstract of DOI:10.1016/j.tetlet.2016.06.125

Fe₃O₄-CTAB NPs have been applied as a competent catalyst for one-pot synthesis of nitriles directly from aldehydes. The present investigation describes the synthesis of nitriles by combination of aromatic/aliphatic/heterocyclic aldehydes and hydroxylamine hydrochloride in the presence of iron oxide nanocatalyst in DMF under reflux condition. Fe₃O₄-CTAB NPs were prepared by reported method and characterized by FE-SEM, TEM, and XRD analysis. The amount of Fe in Fe₃O₄-CTAB was quantified by Atomic Absorption Spectroscopy (AAS). The protocol endow with excellent yield of products along with simple reaction set up and economically adept alternative approach.

Full text of DOI:10.1016/j.tetlet.2016.06.125

Accepted Manuscript
Fe O -nanoparticles catalyzed an efficient synthesis of nitriles from aldehydes
3
4
Pranab Ghosh, Bittu Saha, Gyan Chandra Pariyar, Abiral Tamang, Raju Subba
PII:
S0040-4039(16)30804-8
DOI:
http://dx.doi.org/10.1016/j.tetlet.2016.06.125
TETL 47852
Reference:
To appear in:
Tetrahedron Letters
Received Date:
Revised Date:
Accepted Date:
12 May 2016
26 June 2016
27 June 2016
Please cite this article as: Ghosh, P., Saha, B., Pariyar, G.C., Tamang, A., Subba, R., Fe O -nanoparticles catalyzed
3
4
an efficient synthesis of nitriles from aldehydes, Tetrahedron Letters (2016), doi: http://dx.doi.org/10.1016/j.tetlet.
016.06.125
2
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Fe
3
4
O -nanoparticles catalyzed an efficient synthesis of nitriles from aldehydes
a*
a
a
b
a
Pranab Ghosh , Bittu Saha , Gyan Chandra Pariyar , Abiral Tamang and Raju Subba
O
Fe O Nps
N
3
4
H
NH OH.HCl
DMF/Reflux
2
R
R

1
Tetrahedron Letters
Fe O -nanoparticles catalyzed an efficient synthesis of nitriles from aldehydes
3
4
a*
a
a
b
a
Pranab Ghosh , Bittu Saha , Gyan Chandra Pariyar , Abiral Tamang and Raju Subba
a
Department of Chemistry, University of North Bengal, District Darjeeling-734013, West Bengal, India.
Department of Physics, Jadavpur University, Jadavpur, Kolkata-700032, India.
b
Tel.: +91 (0353) 2776381; fax: +91 (0353) 2699001.
E-mail address: pizy12@yahoo.com (P. Ghosh).
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
3 4
Fe O -CTAB NPs have been applied as a competent catalyst for one-pot synthesis of nitriles
directly from aldehydes. The present investigation describes the synthesis of nitriles by
combination of aromatic/aliphatic/heterocyclic aldehydes and hydroxylamine hydrochloride in
the presence of iron oxide nanocatalyst in DMF under reflux condition. Fe
prepared by reported method and characterized by FE-SEM, TEM and XRD analysis. The
amount of Fe in Fe -CTAB was quantified by Atomic Absorption Spectroscopy (AAS). The
3 4
O -CTAB NPs were
Available online
3
O
4
Keywords:
Aldehydes
Nitriles
protocol endow with excellent yield of products along with simple reaction set up and
economically adept alternative approach.
Fe
DMF
3
O
4
-CTAB NPs
2
009 Elsevier Ltd. All rights reserved.
Reflux
Introduction
3 4
protocol, we have chosen Fe O -CTAB NPs catalyst for our
present investigation. We believe that our investigation will
definitely robust the synthetic approach and fulfil the paucity of
sustainable development.
Suitably design organonitrile derivatives are widely documented
as bioactive molecules (fig. 1). Nitriles are also regarded as
1
prominent intermediate for the production of various2
pharmaceuticals, agrochemicals, polymers, pigments and dyes.
It’s applications in heterocyclic compound synthesis and
functional group transformations are well established from the
CN
O
CN
MeO
MeO
N
N
N
3
MeO
MeO
NH2
long time. Classically adopted methods for nitrile synthesis are
O
N
4
5
OMe
Sandmeyer reaction, ammoxidation of aldehydes, Kolbe nitrile
6
7
synthesis, hydrocyanation of alkenes, and Rosenmund–von
Gallopamil
NO2
Alogliptin
8
Braun reaction. Moreover, various methodologies for single step
9
preparation of nitriles from the substrates like alcohols,
10
11
12
13
amines, amides, azides and oximes are known. The other
O
O
O
1
4
O
alternative approaches are olefinic bond cleavage of alkene,
cyanation of aryl halides, oxidative rearrangement of alkene,
O
O
S
15
16
HO
CN
N
CN
1
7
18
N
H
methyl arenes and benzyl or allyl halides. Preparation of
nitriles from aldehydes is one of the interesting and advantageous
approach because the number of carbon in reactant and final
product will remain same. The main features of one-pot
transformations are valuable strategic way in terms of economic
and environmental aspects. One-pot reactions usually consist of
two or more than two steps that has to be done in a single step
without isolation of intermediate, which in turn, substantially
help to reduces the energy consumption, solvent waste and
reaction time. Focusing on these advantages of one-pot synthesis,
we planned to accomplish single step transformation of
aldehydes into nitriles by means of minimum energy, chemicals
waste and small time outlay. The literature survey reveals that
diverse catalytic systems have been applied for one-pot
Nilvadipine
Febuxostat
Fig.1: Potent bioactive organonitrile derivatives
As iron oxide NPs are well documented in catalysis and
20
medicinal chemistry. The versatile catalytic activity, magnetic
recyclability, low toxicity and useful in medicinal chemistry
21
made it environmentally and economically advantageous. Easy
accessibility and relatively low toxicity made iron NPs a
desirable nanocatalysts in present time. In our endeavour to
develop efficient protocol for nitrile synthesis, we report herein,
Fe O -CTAB NPs catalyzed one-pot synthesis of organonitriles
3 4
from aldehydes and hydroxylamine hydrochloride in DMF under
19
reflux condition (Scheme 1).
transformation of aldehydes into nitriles but most of them are
suffers from various constrain such as harsh reaction conditions,
longer reaction time, low yield, work-up difficulties and waste of
toxic metal salt or solvents into the environment. In view of our
attempt to develop an efficient and environment friendly

2
Tetrahedron Letters
Result and discussion
In continuation of our work for one-pot nitrile synthesis from
2
2
aldehydes and hydroxylamine hydrochloride, we used Fe
CTAB NPs as catalyst for our present investigation. Fe
CTAB NPs were synthesized by reported method (see
supporting information). The synthesized Fe -CTAB NPs were
3
O
O
4
-
-
Fe O Nps-3.7 ppm and .116 AU
3 4
6
5
4
3
2
1
0
3
4
23
3 4
O
then characterized by Field Emission Scanning Electron
Microscope (FE-SEM, INSPECT F50, FEI), Transmission
Electron Microscope (TEM, JEOL, JEM 2100, 200 kV) and X-
ray Diffraction (XRD, Advance D8, Bruker) analysis. FE-SEM
images (fig. 2a) reveal that the Fe
which is further confirmed by the TEM images (fig.2b). TEM
images also reveal that the Fe NPs are in crystalline cubical
shape. XRD spectra shows the standard peaks of the Fe are
unhindered by the CTAB presence although peak broadening has
occurred due to the nano-size of the Fe . Moreover, we have
compared XRD pattern of freshly prepared Fe -CTAB NPs
fig.2c [B]) with literature XRD pattern of pure Fe magnetite
NPs (fig.2c [A]) and found exactly similar XRD pattern with
Fe magnetite NPs. X-ray diffraction pattern of Fe -CTAB
also confirm the purity of magnetite via the absence of other
phases of iron oxide such as maghemite or hematite in product.
3 4
The quantification of Fe in Fe O -CTAB has been evaluated by
Atomic Absorption Spectroscopy (AAS) using Fe standard
solution as supplied by Sigma Aldrich. Fig.2d depicts the plot of
3 4
O NPs are 20-35 nm in size
3 4
O
3 4
O
0
.00
0.05
0.10
0.15
0.20
Absorbance (AU)
3 4
O
3 4
O
Fig 2d: AAS plot of absorbance versus concentration
(
3 4
O
In an endeavor to begin our present investigation we have
taken vanillin as our model compound. The model reaction
comprising vanillin (0.5 mmol), hydroxylamine hydrochloride
3
O
4
3 4
O
(
3 4
0.75 mmol) and Fe O NPs (7.4 mol %) in dry DMF (5 ml). The
reactions were screened from room temperature to high
temperature (table 1). The excellent yield was found only at high
temperature (entry 6, table 1). The reaction at the temperature
range between 50-70 C furnish only oxime derivative and at 80-
0 C offered a mixture of oxime and nitriles derivatives.
absorbance versus concentration of Fe in Fe
concentration of Fe used during the calibration was 0, 2, 4, 6
ppm. The solution of Fe -CTAB NPs in water was prepared by
3 4
O -CTAB Nps. The
o
o
9
3 4
O
taking 5 mg of the sample in 100 ml water and the absorbance of
the sample were taken. From the absorbance data, the
concentration of Fe in Fe O -CTAB has been found to be 3.7
3 4
After reaching satisfactory result under reflux condition in
short reaction time (table 1), the catalytic potential of Fe O -
3 4
CTAB NPs was tested by reducing the amount of catalyst in
similar reaction condition (table 2). Finally we could be able to
optimize the reaction condition and isolate 96 % yield of nitrile
in minimum reaction time (entry 5, table 2). Further reduction of
amount of catalyst or changing the reaction time could not
produce a good result (entry 6-9, table 2). The % of yield
depends on both amount of catalyst and reaction temperature.
The combination of aldehyde (0.5 mmol), hydroxylamine
ppm (blue) and the percentage of Fe in Fe
found to be 74% by weight.
3 4
O -CTAB has been
3 4
hydrochloride (0.75 mmol) and Fe O NPs (1.8 mol %) in dry
DMF (5 ml) under reflux condition found to be optimized
reaction condition for desired transformation (entry 5, table 2).
For the generalization of our scheme, aldehydes 1-15 were
successfully converted into corresponding nitriles under
2
4
optimized condition (table 3).
3 4
Fig. 2a: FE-SEM images of Fe O -CTAB NPs
O
NH OH.HCl
2
N
H
Fe3O4 NPs (1.8 mol %)
DMF (5 ml), reflux
R
R
3 4
Scheme 1. Fe O NPs catalyzed synthesis of nitriles from aldehydes
3 4
Fig. 2b: TEM images of Fe O -CTAB NPs
Fig. 2c: Comparison of XRD pattern of Fe
XRD pattern of pure Fe NPs [A]
3 4
O -CTAB NPs [B] with literature
3
O
4

3
Table 1
a
Screening of catalytic activity of Fe O -CTAB NPs
3 4
b
o
c
Entry
Fe
3
O
4
-CTAB (mg)
Fe
3
O
4
(mol %)
Temp ( C)
Time (h)
Yield (%)
1
2
3
4
5
6
23.1
7.4
r.t
50
4
4
4
3
3
2
nil
-
-
-
-
-
-
-
-
-
-
-
70
-
80
25
36
97
90
reflux
a
Reaction of vanillin (0.5 mmol), hydroxylamine hydrochloride (0.75 mmol) and Fe
3
O
4
-CTAB NPs (23.1 mg,) in dry DMF (5 ml) at different temperature.
b
c
Amount of Fe
3
O
4
NPs in Fe
3
O
4
-CTAB quantified by AAS. Isolated yield.
Table 2
a
Optimization of catalyst
b
c
Entry
Fe
3
O
4
-CTAB (mg)
Fe
3
O
4
(mol %)
7.4
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
9
23.1
11.5
5.7
5.7
5.7
5.7
3.4
2.3
1.1
1.5
2
97
-
3.7
1.8
2
96
-
1.8
1.5
1
d
1.8
96
1.8
0.5
2.5
4
91
88
83
78
0.9
0.6
0.3
4
a
b
Reaction of vanillin (0.5 mmol), hydroxylamine hydrochloride (0.75mmol) and Fe
3
O
4
-CTAB NPs in dry DMF (5 ml) under reflux condition. Amount of Fe
3
O
4
c
d
3 4
NPs in Fe O -CTAB quantified by AAS. Isolated yield. Optimized reaction condition.
Table 3
Fe NPs catalyzed synthesis of nitriles
O
CN
3
O
4
9
H
1
1.5
2
96
86
91
93
91
87
76
HO
HO
b
Entry
1
Aldehydes
Time (h)
Products
Yield (%)
97
OCH3
OCH3
O
O
CN
CN
H
1
10
H
O
NO2
NO2
CN
H
2
1
93
O
CN
1
1
H
OMe
O
OMe
CN
H
3
4
5
6
1.5
1.5
1.5
1
94
92
86
89
OH
H
O
CN
OH
O
12
13
14
2
CN
CN
H
MeO
MeO
O
CN
CHO
H
H
2
Me2N
Me2N
O
CN
CN
O
O
O2N
HO
O N
CHO
1.5
2
CN
2
O
O
H
H
7
8
1.5
1
87
94
HO
1
5
CHO
CN
CN
OH
OCH3
OH
OCH3
b
Isolated yield.

4
Tetrahedron Letters
Plausible mechanism for Fe
synthesis of nitriles from aldehydes is shown in Sheme 2. Fe
CTAB NPs activate carbonyl carbon for nucleophilic attack by
hydroxylamine. Subsequent deprotonation followed by loss of
water molecule gives rise to the formation of oxime derivatives.
Finally, Fe O -CTAB NPs participate in expulsion of water
3 4
molecule from oxime to give desire product and itself get
regenerated at the end of reaction for consecutive cycle.
3
O
4
-CTAB NPs catalyzed one-pot
4.
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H2O
9
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5
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Conclusion
3 4
In conclusion, we have developed Fe O -CTAB NPs catalyzed an
1
1
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efficient protocol for one-pot conversion of aldehydes into
nitriles from aldehydes (0.5 mmol), hydroxylamine
hydrochloride (0.75 mmol) in dry DMF (5ml) under reflux
condition. Advantage of this protocol includes the use of
inexpensive and relatively less toxic nanocatalyst, excellent yield,
easy reaction setup and easy work-up process.
1
7094-7097.
1
1
8. Zhou, W.; Xu, J.; Zhang, L.; Jiao, N. Org. Lett. 2010, 12, 2888-
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2
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Acknowledgement
One of the authors (B.S) is thankful to BSR, UGC-New Delhi for
financial support.
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3
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Aldehyde (0.5 mmol) and hydroxylamine hydrochloride (0.75
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2
2
4
2
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mmol) were added successively to a solution of Fe
3 4
O -CTAB NPs
(5.7 mg) i.e Fe (1.8 mol%) in 5 ml dry DMF. The mixture was
3 4
O
reflux for appropriate time (table 3). The progress of the reaction
was monitored by TLC. After completion of the reaction, the
solution was poured into 100 ml water and extract with ethyl
acetate, washed several times with water. The combined organic
(i) Cohen, M. A.; Sawden, J. N.; Turner, J. Tetrahedron Lett.
1
2
990, 31, 7223-7226; (j) Bhattacharyya, S.; Pathak, U. Synthesis.
015, 3553-3560.

5
mixture was dried over anhydrous Na
residue was purified by column chromatography on silica gel 60-
20 mesh using petroleum ether/ethyl acetate (95:5) as eluent to
afford the pure nitrile. All the products were characterized by IR,
2 4
SO , concentrated and the
1
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H NMR and C NMR.
HIGHLIGHTS OF OUR WORK:
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. Easy reaction set up.
. Simple and easy workup procedure.
. Economically benefited.