Synthesis of acetamides via oxidative C–C bond cleavage of ketones catalyzed by Cu-immobilized magnetic nanoparticles

Article abstract of DOI:10.1002/aoc.5855

Copper supported on magnetite nanoparticles modified with environmentally friendly ligand tricine was devised for synthesis of acetamides via C–C oxidative cleavage of ketones with amines. The catalyst was characterized using different techniques, including Fourier transform infrared, X-ray diffraction, scannin electron microscopy, vibrating sample magnetometry, thermogravimetric analysis, and energy dispersive x-ray spectroscopy. The protocol showed relatively high yields of acetamide products. Furthermore, the magnetic recovery of the catalyst rendered the overall process fast and efficient. It was used in the reaction for six consecutive cycles with negligible loss of catalytic activity. This research is the first report of application of magnetic nanocatalysts for synthesis of acetamides from ketones of low activity through a C–C bond cleavage strategy.

Full text of DOI:10.1002/aoc.5855

Received: 17 January 2020
DOI: 10.1002/aoc.5855
Revised: 2 April 2020
Accepted: 20 April 2020
F U L L P A P E R
Synthesis of acetamides via oxidative C–C bond cleavage of
ketones catalyzed by Cu-immobilized magnetic
nanoparticles
Elahe Yazdani | Farzane Pazoki
| Arefe Salamatmanesh
|
Masoume Jadidi Nejad | Maryam Kazemi Miraki
| Akbar Heydari
Chemistry Department, Tarbiat Modares
Copper supported on magnetite nanoparticles modified with environmentally
friendly ligand tricine was devised for synthesis of acetamides via C–C
oxidative cleavage of ketones with amines. The catalyst was characterized
using different techniques, including Fourier transform infrared, X-ray
diffraction, scannin electron microscopy, vibrating sample magnetometry,
thermogravimetric analysis, and energy dispersive x-ray spectroscopy. The
protocol showed relatively high yields of acetamide products. Furthermore, the
magnetic recovery of the catalyst rendered the overall process fast and
efficient. It was used in the reaction for six consecutive cycles with negligible
loss of catalytic activity. This research is the first report of application of
magnetic nanocatalysts for synthesis of acetamides from ketones of low
activity through a C–C bond cleavage strategy.
University, Tehran, 14155-4838, Iran
Correspondence
Akbar Heydari, Chemistry Department,
Tarbiat Modares University, P.O. Box
14155-4838. Tehran, Iran.
Email: heydar_a@modares.ac.ir
K E Y W O R D S
amide, C–C oxidative cleavage, copper-immobilized magnetic nanoparticles, ketone
1 | INTRODUCTION
problems, a new protocol has emerged. Recently, oxida-
tive C–C bond cleavage has been explored,[18–22] but this
Amides are an important class of organic compounds.
They are widespread in natural products, pharmaceuti-
cals, and other industrial materials,[1] and are extensively
used as synthetic intermediates.[2,3] The antitumor,
antibacterial, and anti-inflammatory characteristics of
the amide functional group make it suitable for medici-
nal chemistry.[4–8] There are diverse methods for the syn-
thesis of the amide functional group, such as amination
of activated carboxylic acid derivatives,[9] direct acid and
amine coupling,[10] Beckman rearrangement,[11] oxida-
tive amidation,[12–15] and cross-coupling reactions.[16,17]
However, these synthetic procedures suffer from high
sensitivity to moisture, side reactions, not being economi-
cal, and harsh reaction conditions. To overcome these
strategy is rarely reported for synthesis of amides.
The pioneering work on synthesis of amides via oxidative
C–C bond cleavage was the unexpected findings of
Ballini et al. in 2003.[23] The concept explored further in
the following years, but there are several drawbacks
and limitations in the reported protocols such
as narrow scope, high activity of ketone substrate,
hazardous and expensive reagents, and use of radical
initiators.[24–29] Moreover, in spite of the application of
many homogeneous and heterogeneous catalysts
designed for this process, almost all of them could not
overcome the obstacle of inactivity of the simple ketones
in the procedure.[24–27]
Recently a novel protocol for synthesis of amides
from ketones taking advantage of the C–C bond
cleavage strategy has been devised which avoids
This article is dedicated to memory of Naser Shabani.
Appl Organomet Chem. 2020;e5855.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5855

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YAZDANI ET AL.
the drawbacks of previous ones.[30] However, this protocol
suffers from cumbersome separation of catalyst from the
reaction mixture, lack of recyclability, and relatively high
loadings of copper as the catalyst. To address these issues,
using of superparamagnetic nanoparticles was proposed.
Superparamagnetic nanoparticles are widely applicable
in different areas of science and technology.[31] Amongst
different types of magnetic nanoparticles, iron oxides
and especially magnetite (Fe3O4) are of considerable
interest due to their properties, such as high surface
area, ecofriendliness, thermal stability, and very high mag-
netic remanence.[32] Despite these useful properties,
bare magnetite nanoparticles are not active enough to cat-
alyze the reactions of interest. Furthermore, unmodified
magnetite nanoparticles are not sufficiently stable under
different chemical conditions. Modification of the sur-
face of magnetite nanoparticles is therefore necessary in
chemical processes. Fortunately, this is straightforward
because of there are many hydroxyl groups on the
external surface of nanoparticles.[33] In industry, there is
interest in simplifying the reagents, conditions, and
catalysts required for a specific operation. We therefore
chose one of the simplest ligands for surface modifica-
tion with easy linkage to the support as well as high che-
lating power to reduce leaching of copper ions to the
solvent. With this goal in mind, we modified the surface
of magnetite nanoparticles with a novel environmentally
favorable ligand, tricine. Tricine is an analog of glycine
(from which it gets its name) that has applications in
buffer solutions and electrophoresis.[34]
(λ = 1.78897 Å), 40 kV voltage, 40 mA current, and in
the range 10–90ꢀ (2θ) with a scan speed of 0.020ꢀs−1
.
Scanning electron microscopy (SEM; Philips XL
30 and S-4160, Netherlands) was used to study the
catalyst morphology and size. Magnetic saturation of the
catalyst
was
investigated
using
a
vibrating
magnetometer/alternating gradient force magnetometer
(MDK Co., Iran). Thermogravimetric analysis (TGA)
was conducted using a thermal analyzer with a heating
rate of 20ꢀC min−1 over a temperature range of
25–1,100ꢀC under flowing nitrogen. The hydrodynamic
diameter of the nanoparticles was measured using a
Zetasizer Nano MAL1001767 (Malvern Instruments,
Malvern, UK) by dynamic light scattering with the
nanoparticles sonicated in water before the measure-
ment. 1H NMR spectra were recorded with a Bruker
Avance (DRX 500 MHz, DRX 250 MHz, US) in pure
deuterated dimethylsulfoxide (DMSO) solvent with
tetramethylsilane as an internal standard.
2.2 | Preparation of copper-immobilized
tricine-modified magnetite nanoparticles
(MN-Tric-Cu)
2.2.1 | Preparation of tricine-modified
magnetite nanoparticles (MN-Tric)
Magnetite nanoparticles were prepared according to the
previously reported literature.[35] To a vigorously stirred
solution of 10 mmol FeCl3.6H2O, 5 mmol of FeCl2.4H2O,
3 mmol of tricine in 40 ml of deionized water at 80ꢀC,
and 10 ml of aqueous ammonia solution (25% w/w)
were added in small portions. After 6 hr, the resulting
black solid was magnetically filtered and washed several
times with water until it reached pH 7. Then the
nanoparticles were washed twice with ethanol and dried
at ambient temperature.
In our ongoing attempts to synthesize efficient
environmentally benign catalysts, we devised
a
novel heterogeneous catalytic strategy for C–C bond
cleavage synthesis of amides. The use of magnetite
nanoparticles as a catalyst bed enables easy separation
of catalyst from the reaction mixture with the aid of a
permanent magnet. This is the first report of such an
application in the C–C bond cleavage synthesis
of amides.
2 | EXPERIMENTAL
2.1 | General remarks
2.2.2 | Immobilization of copper acetate
on the surface of tricine-modified magnetic
nanoparticles (MN-Tric-Cu)
All chemicals and solvents were purchased from
commercial suppliers and used without further
purification. Fourier transform infrared (FT-IR) spectra
were obtained over the region 400–4,000 cm–1 with
a Nicolet IR100 FT-IR (US) with spectroscopic grade
KBr (Germany). X-ray diffraction (XRD) patterns
were obtained at room temperature with a qPhilips X-
pert 1,710 diffractometer (Netherlands) with Co Kα
First, 1 g of as-prepared tricine-modified magnetic
nanoparticles was dispersed in 40 ml of methanol and
3 mmol of copper acetate, then 1 mmol of KOH was
added. The resulting mixture was stirred under reflux
for 6 hr. Finally, the obtained nanoparticles were
separated using a magnet and washed several times
with water and acetone consecutively.

YAZDANI ET AL.
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2.3 | General procedure for synthesis of
amides
nanoparticles and also free hydroxyl groups of the tricine
ligand. The absorption peak at 1624 cm−1 is due to the
stretching vibration of the carbonyl compound of tricine,
which is slightly shifted downfield compared to free
tricine ligand (1650 cm–1).[36] The peak at 2900 cm−1 can
be assigned to C–H of tricine. Finally, the strong band at
590 cm−1 is due to stretching vibrations of F–O bonds,
which are characteristic of magnetite nanoparticles.
To confirm the complete formation of the spinel
structure, the XRD pattern of the nanoparticles was
obtained (Figure 2). The reported diffraction peaks
of Fe3O4 (JCPDS card no. 74–2,403) were seen at
2θ = 21.13, 34.85, 41.21, 50.30, 62.42, 66.43, and 73.68.
The magnetic properties of the prepared nanoparticles
were studied using VSM in the applied field of −1,000 to
+1,000 Oe (Figure 3). The magnetic saturation of
nanoparticles is 32 emu g−1, which confirms the super-
paramagnetic nature of nanoparticles. Moreover, the
superparamagnetic nanoparticles also have reversibility
and zero remanence.
First, 1 mmol of amine and 1 mmol of acetone were
charged in a round-bottomed flask and 4 ml of
DMSO/CHCl3 (3/1) mixture was added. The mixture was
heated at 120ꢀC for 24 hr. Reaction progress was
monitored using thin layer chromatography. The catalyst
was removed with a permanent magnet and the reaction
flask was flushed a few times with ethyl acetate and the
product extracted with dilute (10%) HCl solution. The
residual amine remained in the aqueous phase as
ammonium salt and a solution of amide product in ethyl
acetate was obtained. After the removal of the solvent
under reduced pressure, the resultant amide product was
obtained (details of amide characterization are provided
in Supporting Information Data S1).
3 | RESULTS AND DISCUSSION
The schematic pathway for the synthesis of the catalyst is
shown in Scheme 1.
The synthesized nanoparticles were characterized
using different spectroscopic and thermogravimetric
techniques, including FT-IR, XRD, VSM, TGA, SEM,
and energy dispersive X-ray spectroscopy. The FT-IR
spectrum of the catalyst (Figure 1) shows an absorption
peak at 3400 cm−1, which is attributed to the stretching
vibration of surface hydroxyl groups of magnetite
FIGURE 2 FT-IR spectra of MN-Tric-Cu
SCHEME 1 Pathway to synthesis of MN-Tric-Cu
FIGURE 1 XRD pattern of MN-Tric-Cu
FIGURE 3 VSM of MN-Tric-Cu

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YAZDANI ET AL.
loss under 200ꢀC) and almost 30% of the material consists
of organic moiety (weight loss between 200 and 600ꢀC).
SEM was applied to survey the morphology of the
nanoparticles (Figure 5). The SEM image shows that the
nanoparticles are spherical and of uniform size.
Successful immobilization of copper ions on the sur-
face of the nanoparticles was demonstrated by EDS
(energy dispersive X-ray spectroscopy) (Figure 6). The
EDS spectrum shows emission peaks for the constituent
elements of the ligand (N, C, O) and the magnetic
core (Fe). The copper content of the nanoparticles
was analyzed using ICP(Inductively coupled plasma)
analysis, which showed 0.4 mmol copper per gram of
nanoparticles.
FIGURE 4 TGA of MN-Tric-Cu
The thermal stability of nanoparticles and the amount
of organic part can be analyzed using thermogravimetric
analysis (TGA) (Figure. 4). The absorbed moisture of the
nanoparticles is about 21% according to the curve (weight
The prepared catalyst was used in the reaction of
amine with acetone. The best reaction conditions were
determined using the reaction of aniline as the model
reaction (Scheme 2). No product was obtained in the
absence of catalyst. When bare Fe3O4 was used, the
product did not form. The reaction was tested in various
conditions (Table 1). It was observed that reaction did
not proceed in any solvent except a little in DMSO. We
therefore examined mixtures of DMSO with other
solvents to find a way to promote the reaction. Using a
mixture of DMSO and CHCl3 resulted in higher yields.
The best ratio of DMSO and CHCl3 was 3/1. Different
amounts of catalyst were also used and a suitable amount
was chosen. Furthermore, the effect of different tempera-
tures on the reaction was surveyed (Table 2).
The reactivity of different amines was tested
under the optimized reaction conditions (Table 3). No
noticeable difference between electron-donating and -
withdrawing substituents was detected.
The reusability of the catalyst was tested using
the model reaction. After completion of the reaction, the
catalyst was removed using magnetic decantation. It was
then washed with ethanol, water, and ether and dried at
40ꢀC then reused for the next run of the reaction. This
process was repeated until a noticeable loss in reaction
yield occurred (five cycles). The results are shown in
Figure 7. The heterogeneity of the catalyst was confirmed
using the hot filtration test and ICP analysis of the
residual reaction mixture.
FIGURE 5 SEM image of MN-Tric-Cu
FIGURE 6 EDS analysis of MN-
Tric-Cu

YAZDANI ET AL.
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TABLE 2
and acetonea
Optimization of reaction temperature for aniline
Entry
Temperature (ꢀC)
Yield (%)b
1
2
3
4
5
6
7
8
9
10
25
–
40
–
SCHEME 2 Acetylation of aniline and acetone
60
–
80
–
100
120
130
140
150
160
70
90
90
92
92
92
TABLE 1
acetonea
Optimization of reaction conditions for aniline and
Entry
Catalyst (mg)
Solvent
Yield (%)b
1
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
40
-
CH2Cl2
–
–
2
CHCl3
3
CH3CN
–
aReaction conditions: amine (1 mmol), acetone (1 mmol), catalyst
(40 mg), DMSO/CHCl3 (each 1 ml), 24 hr.
bIsolated yield
4
EtOH
–
5
MeOH
–
cFe3O4 nanoparticles.
6
H2O
–
7
DMF
–
TABLE 3
acetone
MN-Tric-Cu catalyzed reaction of amines and
8
Toluene
–
9
THF
–
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
DMSO
3
DMSO/CH2Cl2(1/1)
DMSO/CHCl3(1/1)
DMSO/CH3CN
DMSO/EtOH
DMSO/MeOH
DMSO/H2O
DMSO/DMF
DMSO/Toluene
DMSO/THF
DMSO/CHCl3(2/1)
DMSO/CHCl3(3/1)
DMSO/CHCl3(4/1)
DMSO/CHCl3(5/1)
DMSO/CHCl3(3/1)
DMSO/CHCl3(3/1)
DMSO/CHCl3(3/1)
DMSO/CHCl3(3/1)
3
70
3
3
3
3
3
3
3
85
90
88
76
–
40c
80
40d
–
92
–
aNote. DMF, dimethylformamide; DMSO, dimethyl sulfoxide; THF,
tetrahydrofuran.
aReaction conditions: amine (1 mmol), acetone (1 mmol), catalyst
and solvent (each 1 ml), reflux (DMF, DMSO and DMSO mixture,
120ꢀC), 24 hr.
bIsolated yield.
cFe3O4 nanoparticles.
dCopper powder.
aReaction conditions: amine (1 mmol), acetone (1 mmol), catalyst
(40 mg), DMSO/CHCl3 (3/1, 4 ml), 120ꢀC, 24 hr.
bIsolated yield.

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YAZDANI ET AL.
The recycled catalyst was characterized after the sixth
run and showed no significant changes in its structure
(Figure 8).
A comparison between the efficiency of the reported
catalyst with other reports of amide formation from C–C
bond oxidative cleavage of ketones is shown in Table 4. It
is evident that the reported catalyst is more efficient than
the others for much lower copper catalyst loading. This
catalyst can also be recycled for six consecutive cycles,
which is a highly important characteristic in industrial
point of view.
A plausible mechanism for the reaction is represented
in Scheme 3.[30] First, amine and acetone react to form
enamine (step A). Evidence for the enamine intermediate
was confirmed experimentally. Enamine was formed and
isolated according to classical procedures (aniline and
acetone plus a few drops of concentrated sulfuric acid)
and underwent C–C oxidative cleavage reaction under
the optimized reaction conditions.[37] In addition, chloro-
form reacts to hydrochloric acid and dichlorocarbine in
reaction with DMSO (step B). In the next step, a carbine
complex of copper forms which in reaction with enamine
(step C) transfers the carbine moiety to enamine to
undergo cyclopropanation (step D). The copper atom
adds to the C–C bond of cyclopropane to form a copper
complex (steps E and F), which leads to a peroxy-copper
species after oxidation with dioxygen from air (step G).
Next the terminal oxygen of the peroxy complex
FIGURE 7 Reusability of MN-Tric-Cu in the reaction of aniline
and acetone
FIGURE 8 (a) FT-IR, (b) XRD, (c) VSM, (d) TGA, (e) SEM, and (f) EDS of recycled catalyst after the fifth run

YAZDANI ET AL.
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TABLE 4
Entry
Comparison of catalyst efficiency in the C–C oxidative cleavage synthesis of amidesa
Catalyst (mg)
Catalyst loading (mol%)
Yieldb (%)
1
2
MN-Tric-Cu
Cu (OAc)2
1.6
10
90
86
aReaction conditions: amine (1 mmol), acetone (1 mmol), catalyst (40 mg), DMSO/CHCl3 (3/1, 4 ml), 120ꢀC, 24 hr.
bIsolated yield.
SCHEME 3 Proposed
mechanism of the reaction
attacks the nitrogen of the imine intermediate and
dichloroethene forms as the side product (step H). Fol-
lowing attack by the acetate ion on the copper complex,
the initial active catalyst is recycled (step I). In the next
step (step J), after hydrogen exchange with released
hydrogen chloride (step B) and chloride ion attack, the
desired product, acetylated amine, is obtained (step K).
4 | CONCLUSION
We devised a novel heterogeneous copper nanocatalyst
for direct and efficient synthesis of acetamides from
amine and acetone. This synthetic strategy has the
advantage of easy separation of catalyst as well as high
reusability of the catalyst. Furthermore, no sensitive

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YAZDANI ET AL.
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ORCID
Farzane Pazoki https://orcid.org/0000-0001-8616-5591
Arefe Salamatmanesh https://orcid.org/0000-0002-
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Maryam Kazemi Miraki https://orcid.org/0000-0003-
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How to cite this article: Yazdani E, Pazoki F,
Salamatmanesh A, Nejad MJ, Miraki MK,
Heydari A. Synthesis of acetamides via oxidative
C–C bond cleavage of ketones catalyzed by Cu-
immobilized magnetic nanoparticles. Appl
Organomet Chem. 2020;e5855. https://doi.org/10.
1002/aoc.5855