Application of Biosynthesized CuO Nanoparticles Using Rosa canina Fruit Extract as a Recyclable and Heterogeneous Nanocatalyst for Alkyne/Aldehyde/Amine A3 Coupling Reactions

Article abstract of DOI:10.1007/s10562-019-02833-4

Abstract: Copper oxide (CuO) nanoparticles (NPs) were prepared through a biological procedure where the Rosa canina fruit extract was used as a capper and reductant agent. For the three-component reaction of amines, aldehydes and alkynes (A³ coupling), these CuO NPs were used as an effective heterogeneous nanocatalyst. Various propargylamines were obtained in a good yield. Additionally, the reuse and separation of CuO NPs was extremely effective, economical and simple. Graphical Abstract: [Figure not available: see fulltext.].

Full text of DOI:10.1007/s10562-019-02833-4

Catalysis Letters
https://doi.org/10.1007/s10562-019-02833-4
Application of Biosynthesized CuO Nanoparticles Using Rosa canina
Fruit Extract as a Recyclable and Heterogeneous Nanocatalyst
for Alkyne/Aldehyde/Amine A3 Coupling Reactions
Malak Hekmati1
Received: 5 March 2019 / Accepted: 12 May 2019
© Springer Science+Business Media, LLC, part of Springer Nature 2019
Abstract
Copper oxide (CuO) nanoparticles (NPs) were prepared through a biological procedure where the Rosa canina fruit extract
was used as a capper and reductant agent. For the three-component reaction of amines, aldehydes and alkynes (A3 coupling),
these CuO NPs were used as an efective heterogeneous nanocatalyst. Various propargylamines were obtained in a good
yield. Additionally, the reuse and separation of CuO NPs was extremely efective, economical and simple.
Graphical Abstract
Keywords A3 coupling · Propargylamines · CuO NPs · Rosa canina
1 Introduction
to developing various synthetic approaches [6–8]. Though,
the most direct and efective technique for preparing propar-
gylamines is via transition-metal catalyzed three-component
coupling of an aldehyde, an amine and a terminal alkyne,
which is identifed as an A3 coupling reaction [9, 10]. Vari-
ous heterogeneous and homogeneous catalysts have recently
been used to synthesize propargylamine through A3-coupling
reaction based on transition metals such as Zr [11], Mn [12],
Re [13], Fe [14, 15], Ru [16, 17], Co [18], Ir [19, 20], Ni [21,
22], Pd [23] Cu [24–28], Ag [29–31], Au [32–35], Zn [36, 37],
Cd [38] and Hg [39]. Among the diferent transition metals,
copper has mostly been examined as it is cheap, abundant, high
reactive and nontoxic. Although many of the catalytic sys-
tems are homogeneous, their loss at the reaction end reduces
their efcacy, especially in industrial applications. Currently,
In most cases, propargylamines are used in organic chemistry
as useful construction blocks and precursors to prepare various
nitrogen-containing heterocyclic materials and main interme-
diates to synthesize natural products and biologically active
drugs [1–3]. Furthermore, a number of propargylamines have
been used to treat neuropsychiatric illnesses such as Parkin-
son’s and Alzheimer’s disease [4, 5]. Their importance leads
* Malak Hekmati
mhekmatik@yahoo.com
1
Department of Organic Chemistry, Faculty
of Pharmaceutical Chemistry, Tehran Medical Sciences,
Islamic Azad University, Tehran, Iran
Vol.:(0123456789)
1 3

M. Hekmati
metal NPs are regarded as heterogeneous catalysts with a high
surface-to-volume ratio. They could be appropriate substitute
for traditional catalysis owing to their higher selectivity and
activity [40–45].
of deinonized water, 10 g of the fruits were added and boiled
in a water bath for 15 min. This mixture was cooled of
and fltered using Whatman flter paper No. 1 to obtain an
aqueous extract. The extract was then stored at 4 °C in a
refrigerator for later use as a reducing and stabilizing agent.
A 10 mL extract quantity was added dropwise to 100 mL
of 1 mM aqueous Cu(OAc)2 solution refuxed at a tempera-
ture of 100 °C for 1 h to obtain the CuO NPs. Owing to the
heating process, the mixtures coloration slowly changed to
a dark brown hue over time. This issue is owing to the sur-
face plasmon resonance excitation signaling the antioxidant
phenolics hydrogen donation behavior and CuO NPs crea-
tion within the plant. Then, the obtained precipitation was
rinsed three times with chloroform and ethanol, respectively.
Afterward, it was air dried for 48 h at room temperature. The
concentration of copper oxide was 5.6 mmol/g, which was
determined by ICP-AES.
Diferent chemical transformations have recently been per-
formed under the heterogeneous catalysis. Among heterogene-
ous catalysts, metal NPs such as CuO have been extensively
used as efcient catalysts in organic reactions owing to their
great surface areas, small dimensions, simplicity, excellent
catalytic activity, benign character and recoverability [46–50].
Furthermore, copper oxide NPs and copper are cheap in com-
parison to Au, Ag, Pd, Pt, Ru and Rh, which have been exten-
sively applied as catalysts for organic transformations.
Various ways exist to synthesize CuO NPs like sonochemi-
cal [51], microwave irradiations [52], sol–gel method [53],
one step solid-state reaction technique at ambient temperature
[54], electrochemical approaches [55], precipitation–pyrolysis
[56], thermal decomposition of precursor [57] or by combin-
ing electro deposition and self-catalytic mechanism. Poison-
ous substances (e.g. hydrazine hydrate, sodium borohydride,
dimethylformamide, ethylene glycol and so on) in chemical
techniques are highly reactive with many biological and eco-
logical difculties. As a result, a challenge existed for fnding
a mild, harmless, suitable and a natural product to produce
metal/metal oxides in an aqueous environment. In diferent
natural materials used to construct NPs, herbs appear to be
the most appropriate candidates as the NPs made using herbs
are more stable and the synthesis speed is high. At present,
simplicity, inexpensiveness and environmentally-friendliness
of green synthesis of NPs have made it extremely important.
Several reports, including those of Aloe barbadensis Miller
[58, 59] and Gum Karaya [60] are available about biosynthesis
of CuO NPs using herbs.
2.2 General Procedure for the Synthesis
of Propargylamine Derivatives
The CuO NPs catalyst (10 mg) was poured to a mixture of
aldehyde (1 mmol), phenylacetylene (1.2 mmol) and amine
(1 mmol) in toluene (3 mL), and the mixture was agitated at
100 °C. The reaction development was controlled through
TLC. After converting the substrate fully, the mixture was
centrifuged after cooling down to ambient temperature. The
crude product was obtained after isolation of the catalyst
and evaporation of the solvent. For purifcation, silica gel
column chromatography (70:30, Hexane/EtOAc) was uti-
lized. Through melting points or spectral analysis, all the
compounds were identifed and their characterization was
carried out [75–88].
Indeed, green synthesis of NPs has been enhanced as a
novel nanobiotechnology to produce economical and eco-
friendly synthetic method for extremely stable NPs. For the
frst time, owing to our considerable interest in the biosyn-
thesis of metal NPs and heterogeneous catalysts [61–73],
we intend to report application of green synthesized CuO
NPs as an efective heterogeneous nanocatalyst for the three-
component reaction of amines, aldehydes and alkynes (A3
coupling) using Rosa canina fruit extract [74]. Moreover,
the CuO NPs can be recovered and recycled several times
without much activity loss.
3 Results and Discussion
The FESEM and TEM measurements were applied to verify
the nanostructure of green synthesized CuO NPs using Rosa
canina fruit extract that was synthesized again according our
previously report [74]. The FESEM image indicated that
the CuO nanoparticles were encapsulated by biopolymers
(Fig. 1a), and surface morphology of the CuO NPs had more
regular stacked structure. TEM image of CuO NPs showed
that this nanoparticle formed evenly dispersed nano-sized
encapsulated in membranous light gray biopolymers shells
(Fig. 1b). Most of these particles are in the 20–25 nm range.
The EDX showing the presence of C, N, O, and Cu in Fig. 1c
also confrmed the existence of biopolymers layers on the
surface of CuO NPs.
2 Experimental
2.1 CuO NPs Green Synthesis Using Rosa canina
Fruit Extract
The polyphenolic compounds have been demonstrated as
reducing agent during the biological extract mediated prepa-
ration of nanomaterials [48, 49]. The Rosa canina extract
After carefully cleaning and washing the fresh Rosa canina
fruits with double-distilled water several times, to 100 mL
1 3

Application of Biosynthesized CuO Nanoparticles Using Rosa canina Fruit Extract as a Recyclable…
Fig. 1 a FESEM, b TEM, and c EDX data of biosynthesized CuO NPs
is also a rich source of the polyphenolic compounds and
favonoidic groups. These entire polyphenolic compounds
may act as reducing agent for the reduction of Cu2+ ion.
Scheme 1 shows the schematic representation of probable
mechanism. In the frst step, when extract mixed with the
metal salt solution, the hydroxyl groups of the polyphenolic
compounds formed the complex with the Cu2+ and reduced
it into the Cu. Thus formed metallic copper atoms react with
the available atmospheric oxygen to form most stable oxide
i.e. CuO. In the next, formed CuO molecules come together
to nucleate followed by further growth which results the
formation of nanoparticles.
Using benzaldehyde, morpholine and phenylacetylene, pri-
mary tests were conducted to optimize diferent factors such
as time, temperature, solvents and catalyst loading. Table 1
presents the outcomes. In this regard, the efect of catalyst
was frst studied, and as expected, desired product was not
obtained without catalyst presenting the dispensable role
of CuO NPs in the reaction mechanism (Table 1, entry 1).
Using a 10 mg catalyst in toluene at 80 °C, the reaction
yield was obtained 85% (Table 1, entry 2). In addition, the
reaction quantitatively occurred using 10 mg of catalyst at
100 °C (Table 1, entry 3). By decreasing the catalyst level
to 7 and 5 mg, lower yields were achieved (Table 1, entries
4 and 5). However, using 10 mg of catalyst in other sol-
vents such as CH2Cl2, DMF, EtOH, H2O, CH3CN and neat,
resulted in lower reaction yields (Table 1, entries 6–11). As
a result, we opted toluene as the best solvent, 10 mg catalyst
and 100 °C reaction temperature as the most optimum and
Owing to our constant interest in the biosynthesis of
metal NPs and heterogeneous catalysts [61–73], after struc-
tural characterization of the prepared CuO NPs, their cata-
lytic activity was studied in the three-component coupling
reaction of amines, aldehydes and alkynes (A3 coupling).
1 3

M. Hekmati
Scheme 1 Probable mechanism
for formation of CuO NPs using
Rosa canina extract
Cu
OH
O
O
Cu2+
n
OH
100oC
O
O
R
R
R
n
n
n
+
Cu0
n
n
100oC
O2
wth
Gro
Nucleation
CuO
CuO NPs
Table 1 Optimization of various conditions in the model reaction using biosynthesized CuO NPs catalyst
O
CHO
+
N
CuO NPs
O
N
H
Entry
Catalyst (mg)
Solvent
T (°C)
Yield (%)a
1
2
3
4
5
6
7
8
–
Toluene
Toluene
Toluene
Toluene
Toluene
CH2Cl2
DMF
EtOH
H2O
CH3CN
–
80
80
100
100
100
70
100
80
100
70
–
10
10
7
85
96
65
50
30
65
60
50
60
35
5
10
10
10
10
10
10
9
10
11
100
Reaction conditions: Benzaldehyde (1.0 mmol), morpholine (1 mmol), phenylacetylene (1.2 mmol), CuO NPs, solvent (3.0 mL) for 10 h
aYields are based on 1H NMR
efective reaction conditions to study the scope of this A3
coupling.
demonstrate that aromatic aldehydes behavior such as func-
tional groups as –Cl, –Br, –OH, –Me, or –OMe can afect the
A3-coupling. Furthermore, minor electronic infuence was
found that is associated with reaction of aryl aldehydes with
electron-withdrawing groups (Table 2, entries 2–4) and gen-
eration of the relevant products in excellent yields, whereas
replacement of electron rich groups (Table 2, entries 5–7) on
the benzene ring lowered the performance and caused less
yields. Furthermore, reaction of challenging heterocyclic
Under optimal reaction conditions, other aldehydes
reacted with various phenylacetylene and aliphatic amines,
resulted in the A3 coupling product with good yield
(Table 2). At the primary study of the aldehyde substrate
scope, phenylacetylene and morpholine were used as model
substrates and various aldehydes were studied for the
A3-coupling reactions (Table 2, entries 1–14). The results
1 3

Application of Biosynthesized CuO Nanoparticles Using Rosa canina Fruit Extract as a Recyclable…
Table 2 The reactions of aldehydes, amines and alkynes in the presence of CuO NPs catalyst
R1
R3
R1CHO
CuO NPs
+
NR2
2
R3
R2 NH
2
Entry
R1
Amine
R3
Yield (%)a
Refs.b
1
2
3
4
5
6
7
8
Ph
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
Morpholine
Piperidine
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
96
90
95
92
88
90
85
92
90
90
80
92
90
0
[75]
[85]
[88]
[78]
[86]
[75]
[86]
[86]
[75]
[86]
[86]
[86]
[87]
[86]
4-ClC6H4
3-ClC6H4
4-BrC6H4
4-OHC6H4
4-MeC6H4
4-OMeC6H4
2-Thiophenyl
2-Furfuryl
Cyclohexyl
C3H7
9
10
11
12
13
14
Ph
Ph
Ph
Pyrrolidine
Aniline
Reaction conditions: Aldehyde (1.0 mmol), amine (1 mmol), alkyne (1.2 mmol), CuO NPs (10 mg) were stirred in toluene (3.0 mL) at 100 °C
for 10 h
aYields are based on 1H NMR
bEarlier reference of the corresponding product
compounds like thiophene-2-carbaldehyde or furan-2-car-
boxaldehyde with morpholine and phenylacetylene ef-
ciently proceeded, and the corresponding propargylamines
were obtained in good yields (Table 2, entries 8, 9). Moreo-
ver, under this optimum condition, the aliphatic aldehyde
(cyclohexanecarbaldehyde/butanaldehyde) indicated good
yields (Table 2, entries 10, 11). A mixture of benzaldehyde-
phenylacetylene-amine was selected to expand the scope
of amine substrates, and various amines were examined
(Table 2, entries 1 and 12–14). The results show that under
optimal reaction conditions, cyclic, heterocyclic (piperidine/
Fig. 2 Recycling of catalyst for the reaction of benzaldehyde, mor-
pyrrolidine/morpholine) provided high yields of products
pholine and phenylacetylene
(Table 2, entries 1 and 12, 13). However, no product was
achieved by using aniline as a substrate (Table 2, entry 14).
Recovery of heterogeneous new catalysts is particularly
essential in terms of economic and sustainable chemistry
views. As a result, we studied the recovery of the CuO NPs
catalyst for the reaction of benzaldehyde, morpholine and
phenylacetylene under optimum reaction conditions. For this
purpose, at the end of the reaction, through centrifugation
and rinsing with water and ethanol twice, the catalyst was
isolated from the reaction solution. Afterward, the catalyst
was recycled for seven times with observing no signifcant
change in the catalytic performance (Fig. 2). This reusabil-
ity demonstrates the excellent turnover and stability of the
catalyst under working conditions.
In addition, to stablish the catalyst heterogeneity, for the
reaction of benzaldehyde, morpholine and phenylacetylene,
a hot fltration examination was performed using CuO NPs
under the optimized conditions. After 5 h a 65% yield could
be achieved from the reaction, and subsequently the catalyst
was separated to be reapplied. No increase in yield of the
1 3

M. Hekmati
Table 3 Comparison efciency
of CuO NPs with some
Entry
Reaction conditions
Time (h)
Yield %
Refs.
reported methods for the A3
coupling reaction between
benzaldehyde and piperidine
with phenylacetylene
1
2
3
4
5
6
7
8
CuO NPs, toluene, 100 °C
AgI, H2O, 100 °C, N2
CuSBA-15, toluene, 90 °C
Au@PMO-IL, CHCl3, 60 °C
FeCl3, 70 °C
Ag NPs, PEG, 100 °C
Nano Co3O4, 130 °C
Fe3O4, toluene, 80 °C
Fe3O4@SBA-15, toluene, 110 °C
NiCl2, toluene, 111 °C
Ag-NaY, neat, 100 °C
Ag NPs/plant extract, PEG, 90 °C
MNP@Au/NNN-pincer, H2O, 85 °C
10
14
6
12
14
20
15
16
8
96
70
80
87
34
77
87
75
76
87
73
83
90
92
This work
[76]
[77]
[78]
[79]
[80]
[81]
[82]
[83]
[84]
[85]
[48, 49]
[86]
[87]
9
10
11
12
13
14
9
15
18
7
[CuCl{2,5-bis(2-thienyl)-1-phenylphosp-
5
hole}2], 100 °C
15
InBr3, toluene, 80 °C
6
80
[88]
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Table 3 presents a comparison of a number of chosen
procedures in the literature and current procedure, showing
that CuO NPs is similarly or more efective catalyst in terms
of yield and reaction time than previously-reported ones.
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In summary, a cost-efective, green, simple efective, tech-
nique was developed to synthesize CuO NPs with Rosa
canina fruit extract as a stabilizer and reductant. It was
determined that CuO NPs were an air stable, efective and
cost-efective catalyst to synthesize propargylamines using a
one-pot three-component A3-coupling reaction of aldehydes,
amines and alkynes. The products were obtained in good to
high yields, and the catalyst can be reutilized up to seven
cycles with almost no performance change.
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Acknowledgements We are thankful to Department of Organic Chem-
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Islamic Azad University, Tehran, Iran for fnancial supports.
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