An efficient magnetic copper ferrite nanoparticle catalysed ligand and solvent free synthesis of N-aryl amide from aldoximes and iodobenzene

Article abstract of DOI:10.1039/c5ra22777a

A simple, efficient, and environmentally benign method has been reported for the synthesis of N-aryl amides using aldoximes and iodobenzene under ligand free and solvent free conditions and using magnetically separable copper ferrite nanoparticles as catalyst. The catalyst was characterised using XRD, FEG-SEM, EDAX, ICP-AES and TEM and tested for recyclability for up to five cycles.

Full text of DOI:10.1039/c5ra22777a

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DOI: 10.1039/C5RA22777A
Journal Name
ARTICLE
An efficient magnetic copper ferrite nanoparticle catalysed ligand
and solvent free synthesis of N-aryl amide from aldoximes and
iodobenzene.
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
a
Sachin A.Sarode Jeevan M. Bhojane and Jayashree M.Nagarkar
DOI: 10.1039/x0xx00000x
A simple, efficient, and environmentally benign method has been reported for the synthesis of N-aryl amides by using
Aldoximes and Iodobenzene under ligand free and solvent free conditions using magnetically separable copper ferrite
nanoparticles as catalyst. The catalyst was characterised by using XRD, FEG-SEM,EDAX,ICP-AES and TEM and tested for
recyclability up to five cycles.
www.rsc.org/
1
2
amines for the synthesis of N-aryl amides are also reported.
Most of the above reported reactions take place in solvent
Introduction
medium. However, the reaction in solvent free condition has
1
3
great importance in the area of green chemistry.
Magnetically separable nanoparticles as catalysts have
N-aryl amides are important moieties in the medicinal
14
attracted much attention in organic reactions.
These
Particularly, copper ferrite
chemistry which are the backbone of many pharmaceutical
1
nanoparticles have shown large surface to area ratio, good
and biologically active natural products.
The medicinal
15
activity and reusability.
nanoparticles possess good catalytic activity when employed in
chemistry database discovered that, the amide bond appears
1
6
in more than 25
% of known pharmaceutical active various organic transformations. Here, we propose the
2
ingredients. Additionally, amides are very useful building
blocks in organic synthesis, and are precursors for many
solvent and ligand free, magnetically separable copper ferrite
nanoparticles, as catalyst for the coupling reactions between
1
7
valuable compounds such as agrochemicals, polymers and
aldoximes and aryl halides to get N-arylated amides.
This
3
organic materials. Eventually, the amide bond formation
protocol overcomes the drawback of regioselectivity and
moreover, it is the first report, on the said reaction by using
heterogeneous catalyst.
reactions play an important role in achieving green chemistry
4
perspective in organic synthesis. However, traditional trans
amide formation reactions are usually carried out by using
coupling reactions between corresponding acids or acid
5
chlorides with amines. The rearrangement of ketoximes in
presence of strong acids, gives the straightforward product of
6
trans amide. Both the above traditional methods have some
drawbacks such as high temperature, strong acidic conditions,
7
and hazardous waste. There are various methods of synthesis
of N-aryl amide using the aryl halide (Scheme 1). Aldoximes on
sequential reaction of hydration and dehydration in presence
8
of transition metals, give primary amides. Recently ‘Panda et
al.’ reported copper catalysed homogeneous coupling reaction
9
of aldoximes and aryl halides to afford N-aryl amides directly.
There are many reports on formation of trans amide by using
coupling reaction between primary amides and aryl halides,
with various homogenous and heterogeneous catalytic
1
0
systems.
In situ hydration of benzonitrile and coupling
11
reactions with aryl halide was also reported. Green and
heterogeneous catalytic coupling reactions of amides and
a
Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai –
4
+
†
00019, India. E-mail: jm.nagarkar@ictmumbai.edu.in; Fax: +91 22 33611020; Tel:
91 22 33611111/2222
Footnotes relating to the title and/or authors should appear here.
Scheme 1: Various methods of N-aryl amide formation using aryl
halides
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
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Journal Name
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DOI: 10.1039/C5RA22777A
Experimental
Catalyst was prepared by using known simple co-precipitation
1
5b
followed by thermal decomposition method. Copper (II) nitrate
4.1 mmol) and iron (III) nitrate (8.2 mmol) were taken in
(
stoichiometric proportions and 100 mL of deionised water was
added to produce clear solution. 1M NaOH solution was added drop
wise under stirring to the above solution till the pH becomes
1
0.Reddish-black precipitate of copper ferrite was formed. The
reaction mixture was warmed to 90°C and stirred for 2h which on
cooling gave magnetic particles. The catalyst was then washed with
water and ethanol and separated by using a magnet. It was kept in
air oven at 80°C for 12 h. Then the catalyst was grinded in a mortar-
pestle and kept in a furnace at 700°C for 5 h. It was then cooled to
room temperature slowly to get the magnetic copper ferrite NPs.
Characterization of material
Synthesized catalyst was characterized by various techniques such
as X-ray diffraction (XRD), Field emission gun Scanning electron
microscopy (FEG-SEM) and Transmission electron microscopy
Figure 1: X-ray diffraction spectrum of fresh copper ferrite
nanoparticles (A) and after the fifth cycle (B)
(
TEM). The XRD analysis was performed on Shimadzu XRD 2400
instrument using Cu Kα radiation (λ= 1.5406 A°) with scanning rate
2
2
degree per minute. TEM analysis was performed over PHILIPS
200 instrument. FEG-SEM analysis was performed on 25 TESCAN
MIRA Instrument. The energy dispersive X-ray spectral analysis
EDS) image was recorded with an Oxford instrument at 10 kV.
(
Beam intensity was kept high to get good response by the detector.
GC analysis is performed over PerkinElmer Clarus 480 instrument.
GC-MS Spectra recorded over Shimadzu QP-2010 Instrument. 1H
spectra’s were recorded on Agilent 400MHz
Result and Discussion
XRD analysis showed peak at 2θ = 30.1, 35.14, 43.41, 54.601, 40
5
(
1
7.0671and 63.6651 which represent the Bragg reflections from the
220), (311), (400), (422), (511) and (440) planes respectively (Figure
A). XRD pattern of prepared copper ferrite nanoparticles shows
the tetragonal structure with good crystallinity (JCPDS card No. 034-
15
0
425). We found the same XRD pattern of the recycled copper
ferrite nanoparticles after the fifth cycle of reaction (Figure 1 B ).
Elemental analysis of nano CuFe O was confirmed by EDS ( Figure 2
2
4
E
E) and ICP-AES. Elemental analysis gave the copper – Iron ratio as
:2 approximately. ICP-AES study shows the 0.00026 mmol/g of
1
copper and 0.00056 mmol/g of iron in the catalyst. The particle size
of nano copper ferrite measured by using the TEM was found in
between 11-14 nm (Figure 2 B). FEG-SEM analysis shows the
crystalline nature of the copper ferrite nanoparticles. The FEG-SEM
analysis shows the same morphology of the nanoparticles after the
fifth cycle of the reaction (Figure 2 A-C). The FEG-SEM analysis of
the reaction mass clearly shows the homogenisation of the catalyst Figure 2: Scanning electron microscopy images of copper ferrite
(
Figure2 D).
nanoparticles before (A),after Five cycles (C) and after the reaction without
washing of organic compounds (D).Transmission electron microscopy of
cooper ferrite nanoparticles (B). EDAX of copper ferrite nanoparticles (E)
2
| J. Name., 2012, 00, 1-3
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Journal Name
We started the optimisation of reaction parameters by considering Reaction Conditions:
ARTICLE
A
mixture of iodobenzene (1mmol),
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the reaction between benzaldoxime and iodobenzene. It is treated benzaldoxime (2mmol.), 10 mol% catalyst anDdOIK: 21 C0O.1 03 3(92/Ce5qR.)A2a2t71775A0
b
as a model reaction. Initially we have carried out the reaction °C for 12 h. Isolated yield .
without using the catalyst which gave benzamide as the major
product instead of desired product (Table 2Entry 7). Various copper
a
Table 2 Optimisation of reaction conditions
and iron based catalysts were employed to get the best catalytic
system (Table 1). Copper ferrite NPs were found to be the most
effective catalyst for the model reaction in presence of K CO under
2
3
solvent free condition (Table 1 Entry 8). We also tried model
reaction with various bases. Triethylamine and Na-tert-butoxide did
not even initiate the reaction and starting materials remain
unchanged (Table2 Entry 2-3). The model reaction carried out by
using sodium carbonate, KOH and potassium phosphate afforded
moderate yield, where as K CO gave 88% yield of N-phenyl
2
3
b
benzamide (Table 2 Entry 4-6). Hence K CO was used as a base
Entry Solvent Base
Mol % Yield
2
3
throughout the optimisation of reaction conditions (Table 2 Entry
). The reaction was also carried out in various solvents, where in
1
more amount of benzamide was obtained decreasing the yield of
coupling product N-phenyl benzamide (Table 2 Entry 11-15). When
the reaction was carried out at 100 °C, it afforded only 40% yield.
The reaction carried out at 160°C did not show any significant
increase in the product yield. The optimised catalyst concentration
was found to be 10 mol %. The model reaction carried out by using
Neat
Neat
Neat
Neat
Neat
Neat
Neat
Neat
Neat
10
10
88
ND
ND
68
73
56
ND
48
65
90
1
2
3
4
5
6
7
8
9
1
1
1
1
1
K2CO3
TEA
5
and 7.5 mol% of the catalyst, offered 48% and 65% yield
Na-tertbutoxide 10
respectively whereas 12% catalyst loading did not show significant
increase in the product yield (Table 2 entry 7-9).
KOH
10
10
10
-
Table 1 Synthesis of N-aryl amides by using different Cu and Fe
based catalysts
a
2 3
Na CO
b
Entry Catalyst
Yield
K
K
K
K
3
2
2
2
PO
4
1
2
3
4
5
6
7
8
CuI
43
d
CO
3
CO
3
CO
3
CuO (Bulk)
CuSO4
45
5
ND
68
7.5
Cu O (Nano)
2
0
1
2
3
4
Neat
K
K
2
CO
3
3
12
10
FeCl .6H O
53
C
3
2
Toluene
2
CO
54
45
43
36
Fe O
3
55
4
C
DMF
NMP
K
K
K
2
CO
2
CO
2
CO
3
3
3
10
10
10
FeSO4
ND
C
C
Copper ferrite NPs 88
2
H O
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ARTICLE
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DOI: 10.1039/C5RA22777A
82
C
Ethanol
K
2
CO
3
10
30
15
5
a
Reaction Conditions: Iodobenzene (1mmol), benzaldoxime (2b
mmol.), copper ferrite NPs, base (2 eq.), Neat, 150 °C for 12 h.
6
83
73
C
d
Isolated yield. solvent as medium without catalyst
We applied these optimised reaction conditions to various
derivatives of the aldoximes and iodobenzene to explore and to
check the stability of functional group. We have used different
substrates having electron donating groups as well as bulkier
groups at various positions. We observed that the compound
containing electron donating group on aldoximes gave good yield of
the product (Table 3). The bulkier group also gave moderate yield of
the desired product (Table 3 entry 7). Aryl halides bearing flouride,
methyl, methoxy ,chloride, bromide and -CF3 groups gave
moderate to good yield of the respective products (Table 4). We
7
a
Reaction Conditions: Iodobenzene (1mmol),aldoxime (2mmol.),
b
copper ferrite NPs (10mol %), K CO (2 eq.) Neat, 150 °C for 12 h.
Isolated yield.
2
3
a
Table 4 Reactions of Aryl halides with benzaldoximes
observed
bromoiodobenzene gave the mixture of 2-phenyl benzaoxazole and
bromo-N-phenylbenzamide products (Table 4 Entry 10). Reaction
that
reaction
of
benzaldoximes
with
2-
2
of chlorobenzene and bromobenzene with the benzaldoximes did
not give the desired product under the present reaction conditions.
a
Table 3 Reactions of Aldoximes with Iodobenzene
b
Sr
no.
Aryl halide
R2
Product
Yield
1
85
b
Sr.N Aldoxime
o
Product
Yield
2
3
84
80
R1
1
88
2
3
4
76
86
84
4
5
73
79
4
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DOI: 10.1039/C5RA22777A
6
7
8
9
1
86
83
77
85
Figure 3: Plausible reaction mechanism.
In leaching test, it is very difficult to remove the catalyst from in
between the reaction to study the leaching of copper and iron. We
did the ICP-AES study of the filtrate of reaction mass after the
completion of reaction. ICP-AES study revealed leaching of 0.029
ppm copper and 0.021 ppm iron in the filtrate which is negligible It
confirms the heterogeneous nature of nanoparticles. At the end of
the reaction, the catalyst was seperated by using the magnet from
0
35
45
the crude reaction mixture, washed with ethyl acetate and water,
o
dried at 100 C, and reused as such for succeeding experiments (up
to fifth cycle) under similar reaction conditions. Slight decrease in
the product yield indicates that the catalyst can be reused up to five
cycles (Figure 4).
a
Reaction Conditions: Aryl halides (1mmol), benzaldoxime (2
mmol.), copper ferrite NPs catalyst (10mol %) and K CO (2 eq.)
2
3
b
neat, 150 °C for 12 h. Isolated yield
100
8
8
0
Based on literature reports and our present experimental results a
plausible reaction mechanism has been proposed. We carried out
the control reaction to check the mechanism. In absence of
iodobenzene and optimised reaction conditions the benzaldoximes
get converted to benzamide and benzonitrile. We carried out the
reaction with benzonitrile and iodobenzene under same reaction
conditions but we did not obtain the desired product. It was
confirmed that the dehydration and hydration of benzaldoxime
take place in presence of copper ferrite nanoparticles. Here, in situ
formed benzamide then coupled with iodobenzene on surface of
copper ferrite NPs to give N-arylated amides (Figure 3).
60
40
Yield
20
0
1
2
3
4
5
Figure 4: Recyclability study of copper ferrite NPs catalyst
Conclusions
In conclusion, we have developed the simple and green
protocol for the one pot synthesis of N-aryl amide by using
aldoxime and Iodobenzene as starting material and nano
copper ferrite as a catalyst. The protocol is applicable to
various substrates and afforded moderate to good yields.
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Journal Name
0 (a) C. Wolf, H. Xu Chem.Comm. 2009, 13, 1715.(b) S.N.
1
Solvent free reaction and reusable as well as magnetically
separable heterogeneous catalyst are the main advantages of
the protocol.
View Article Online
Murthy,
Y.V.D.
Nageswar,
K.
Swapna,
Eur.
DOI: 10.1039/C5RA22777A
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1
7 General procedure for N- Arylation of amide
2
An oven-dried Schlenk tube equipped with a magnetic
stirring bar was charged with benzaldoxime (2 mmol),
iodobenzene (1 mmol), Copper ferrite NPs (10mol%), and
K CO (2 mmol). Reaction mixture was heated in an oil bath
(
2
3
7
8
(a) P. D. Bailey, I. D. Collier and K. M. Morgan, in
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ed. A. R. Katritzky, O. Meth-Cohn and C. W. Rees,
2
3
at 150°C and was stirred for 12 h. The reaction was
monitored by GC and TLC. After completion of the reaction,
the reaction mixture was cooled to room temperature and
the reaction mass was diluted with ethyl acetate. Catalyst
separated by using magnet.The resulting filtrate was washed
with water and 20% brine solutions. The organic layer was
separated and dried over anhydrous sodium sulphate. The
solvent was removed under vacuum to get the crude
product, which was purified by column chromatography on
silica gel eluting with the mixture of pet ether / EtOAc (80:
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9
,
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identity of known products are conformed by H NMR and
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,1602–1605.
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RSC Advances
Graphical abstract:
An efficient magnetic copper ferrite nanoparticle catalysed ligand and solvent free synthesis of N-aryl amide from aldoximes and
iodobenzene.
a
Sachin A.Sarode ,Jeevan M. Bhojane and Jayashree M.Nagarkar
a
a
One pot dehydration, hydration and coupling reaction protocol for N-substituted amide formation.
I
O
OH
N
10% Copper ferrite NPs
eq K CO ,Neat
N
H
+
2
2
3
0
1
50 C 12 h