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lable at ScienceDirect
C. R. Chimie 20 (2017) 765e772Contents lists avaiComptes Rendus Chimie
www.sciencedirect.comFull paper/MemoireCopper(II) chelate-bonded magnetite nanoparticles: A new
magnetically retrievable catalyst for the synthesis of
propargylamines
Atefeh Shouli a, Saeid Menati b, Soheil Sayyahi a, *
a Department of Chemistry, Mahshahr Branch, Islamic Azad University, Mahshahr, Iran
b Department of Chemistry, Khorramabad Branch, Islamic Azad University, Khorramabad, Irana r t i c l e i n f o
Article history:
Received 15 January 2017
Accepted 27 March 2017
Available online 3 May 2017
Keywords:
Propargylamines
Magnetic copper-based nanoparticles
Solvent-free reactions* Corresponding author.
E-mail address: sayyahi.soheil@gmail.com (S. Sa
http://dx.doi.org/10.1016/j.crci.2017.03.010
1631-0748/© 2017 Académie des sciences. Publishea b s t r a c t
In this study, we document the use of a reusable magnetic nanoparticle (MNP)-supported
copper catalyst for the efficient synthesis of propargylamines via the A3 coupling of
benzaldehydes, phenylacetylene, and piperidine or morpholine. The new MNPs were
characterized by scanning electron microscopy, energy dispersive X-ray analysis, Fourier
transform infrared spectroscopy, thermogravimetric analysis, and vibrating sample
magnetometry. Notably, the activity and leaching test of the catalyst indicated that the
MNPs could be reused without loss to its catalytic activity or leaching of its copper ligands.
© 2017 Académie des sciences. Published by Elsevier Masson SAS. All rights reserved.1. Introduction
Magnetite [1] is a well-known material that possesses a
highly active surface for the immobilization and adsorption
of catalytic fragments, including organocatalysts, enzymes,
and metal catalysts (such as gold, palladium, platinum,
copper, nickel, cobalt, and iridium), which results in the
formation of remarkably sustainable catalysts. It has been
used as a versatile catalyst support in a wide variety of
reactions, including hydrogenation, reduction, oxidation,
cycloaddition, asymmetric synthesis, and the Suzuki, Heck,
Sonogashira, and Hiyama [2e4]. Recently, the application
of copper-based nanoparticles as a catalyst has generated
much interest. The possible modification of the chemical
and physical properties of the nanoparticles has been
largely responsible for the rapid growth of interest in these
nanomaterials and their applications in catalysis [5].yyahi).
d by Elsevier Masson SAS. APropargylamines are prominent components strike-
through as precursors for the synthesis of various nitrogen-
containing compounds (such as allylamines, pyrrolidines,
oxazoles, and pyrroles) or as intermediates in the prepa-
ration of a diverse range of natural products, biologically
active compounds, and pharmaceuticals (Scheme 1). In
addition, some propargylamines have been found to
possess interesting biological properties (e.g., as inhibitors)
and have even been tested as targets for multifunctional
drugs in the treatment of Alzheimer's and Parkinson's
diseases [6e9].
The catalytic coupling of the aldehydeealkyneeamine
(A3 coupling), the addition of alkyne nucleophiles to C]N
electrophiles, has shown great utility in the simple and
rapid preparation of propargylamines in broadly tolerant
and highly tunable reaction conditions [14]. In this regard,
several catalytic systems using transition metal catalysts
have been developed [15e18]. A review of the literature has
indicated that copper catalysts have played a noteworthy
role in the development of methods for propargylaminell rights reserved.
Scheme 1. Selected compounds with propargylamine skeleton [10e13].
A. Shouli et al. / C. R. Chimie 20 (2017) 765e772766synthesis [5,8,19e28]. In this study, we report the synthesis
and characterization of copper-based magnetic nano-
particles (MNPs) and document their catalytic application
in propargylamine synthesis.
2. Experimental section
2.1. General
All chemicals used in this study were purchased from
commercial sources and used without further purification.
The reaction was monitored by thin-layer chromatography
(TLC) on aluminum-backed silica gel 60 F254plates (0.2mm
thickness, Merck). Atomic absorption measurements were
performed using a Shimadzu AA-6300 spectrometer.
Scanning electron microscopy (SEM) and energy dispersive
X-ray (EDAX) analyseswere carried out using a Philips XL30
instrument for the elemental analysis of the nanoparticles.
The transmission electron microscopy (TEM) image wasScheme 2. Synthesis of copper(II) chelaterecorded using a Zeiss-EM10C at 80 kV. Magnetism analysis
was performed using a vibrating sample magnetometer
(4 in., DaghighMeghnatis Kashan Company, Kashan, Iran) at
room temperature. The Fourier transform infrared (FT-IR)
spectra were acquired on a BOMEM MB-Series 1998 FT-IR
spectrometer using KBr pellets.2.2. Synthesis of Cueimine ligand@SiO2@Fe3O4
To introduce a linker, SiO2@Fe3O4 (2 g) was dispersed in
dry toluene (10 mL) and sonicated for 15 min in an ultra-
sonic bath. After this, (3-aminopropyl) triethoxysilane
(2 mL) was added to the mixture, which was then refluxed
for 72 h under nitrogen. The resultant particles were sepa-
rated magnetically, washed thoroughly with ethanol, and
dried under reduced pressure to obtain Am-SiO2@Fe3O4.
The surface was subsequently modified by adding Am-
SiO2@Fe3O4 (1 g) to a solution of 2-hydroxybenzaldehyde
(1 mmol, 0.122 g) in ethanol (10 mL), and the mixture was
then stirred under reflux conditions for 12 h. The resultant
MNPs were removed using an external magnet, washed
repeatedly with ethanol, and dried to generate imine
ligand@Am-SiO2@Fe3O4. Finally, to synthesize copper(II)
chelate-bonded Fe3O4 nanoparticles, a mixture of Azo
ligand@Am-SiO2@Fe3O4 (2.0 g) in ethanol (10 mL) was
sonicated for 15 min. Then, copper(II) chloride (1 mmol,
0.134 g) was added, and the resulting mixture was refluxed
for 24 h. After the particles were magnetically removed, the
nanocomposites were washed with water and dried under
vacuum.2.3. General procedure for the synthesis of propargylamines
In a test tube, a mixture of aldehyde (1 mmol), phe-
nylacetylene (1.3 mmol), and piperidine or morpholine
(1.3 mmol) was reacted in the presence of copper(II)eimine
ligand@SiO2@Fe3O4 (0.1 g) under solvent-free conditions at
80 C. After the reaction was complete (as monitored by
TLC), the reaction mixture was allowed to cool to room
temperature and diluted with DCM (10 mL). The MNPs-bonded magnetite nanoparticles.
Fig. 1. SEM/EDAX elemental analysis and TEM image of Cueimine
ligand@SiO2@Fe3O4.
A. Shouli et al. / C. R. Chimie 20 (2017) 765e772 767were then separated magnetically, and the organic phase
was washed with water, dried over Na2SO4, and concen-
trated under reduced pressure. The final product was then
subjected to column chromatography (1:4 v/v ethyl ace-
tate/hexane) for further purification.
3. Results and discussions
Our strategy for immobilizing a copper(II)eimine com-
plex onto silica-coated magnetite was based on our previ-
ous work (Scheme 2) [29e31]. The synthetic method
commenced with the surface modification of SiO2@Fe3O4
with (3-aminopropyl) triethoxysilane, which was subse-
quently reacted with salicylaldehyde. We assumed that
these treatments in addition to forming an active site of
imine and hydroxyl groups for chelatewith copper enhance
the lipophilicity of the nanoparticles.
The resulting MNPs were analyzed and characterized by
analytical techniques including SEM, EDAX, FT-IR, ther-
mogravimetric and derivative thermogravimetric (TG-DTG)
analyses, and vibrating sample magnetometry.
A particle size with about ~41e76 nm diameter with a
nearly spherical shape was observed in the SEM and TEM
images of the CuPs. The presence of the main elements
(iron, oxygen, silicon, nitrogen, carbon, copper, and chlo-
rine) was confirmed by EDAX analysis (Fig. 1). In addition,
the copper content was determined to be ~2.5 wt % by
atomic adsorption spectroscopy.
In the FT-IR spectrum of the copper nanoparticles
various peaks in the range of 400e4000 cm1 corre-
sponded to the magnetite and outer silica layers and to the
linker/ligand parts (Fig. 2). The band at ~586 cm1
belonged to FeeO stretching vibration, an intense band at
~1105 cm1 was because of SieOeSi antisymmetric
stretching vibrations, and the presence of a broad band at
~3350 cm1 was attributed to the SieOH group. Also, bands
at ~2850e2926 cm1, weak bands at ~1460e1487 cm1,
and a shoulder band at ~1617 cm1 were associated with
CeH, C]C, and C]N stretching vibration, respectively. In
addition, the band at ~1623 cm1 was attributed to the
water molecules that were adsorbed on the surface [32].
The thermal stability of the Cu(II)eimine ligand@-
SiO2@Fe3O4 was examined by TGA-DTG under nitrogen
atmosphere (Fig. 3). The TGA-DTG data indicate mass loss
corresponding to the removal of physically adsorbed water
up to ~150 C and another one between ~260 and 400 C
that can be attributed to the rapid thermal decomposition
of the linker and ligand moieties.
A vibrating sample magnetometer was used to measure
the magnetic property of the Cu NPs. It can be seen that the
magnetization curves appeared s-shaped over the applied
magnetic field. The samples exhibited typical super-
paramagnetic behavior by showing zero coercivity. This
means that they were related to an external magnetic field
but retained no residual magnetism once the external
magnetic field had been removed at room temperature
[33]. In comparison with the neat Fe3O4, the saturation
magnetization value of copper(II) chelate-bonded Fe3O4
decreased from ~60 to ~24 emu/g, which can be attributed
to the coating of nonmagnetic materials on the magnetite
particles (Fig. 4).It has been demonstrated that the use of solvent-free
conditions in heterocyclic synthesis generally leads to
similar or higher yields compared to the same reaction
performed in the presence of molecular solvents; the re-
action time is also reduced [34]. Accordingly, we performed
a screening of the reaction conditions from the viewpoint
of temperature, amount of reactant, and catalyst at the
outset of this work. As expected, the treatment of benzal-
dehyde, piperidine, and phenylacetylene without catalyst
showed no reaction even at a high temperature (100 C)
over the course of a lengthy reaction time (24 h). In
Fig. 2. FT-IR spectra of Am-SiO2@Fe3O4 and Cueimine ligand@SiO2@Fe3O4.
A. Shouli et al. / C. R. Chimie 20 (2017) 765e772768addition, yields decrease dramatically at lower reaction
temperatures. The scope of the reaction was then explored
under the optimized conditions using a variety of aromatic
aldehyde, phenylacetylene, piperidine and/or morpholine,
and MNPs as catalysts (Table 1).Fig. 3. TG-DTG analysis for CueiOne of themost disadvantages of the use of immobilized
homogeneous catalysts is that the valuable metal is contin-
uously leached and carried away with the products [35]. To
check this issue, a mixture of Cu NPs (1.0 g) in EtOAc (10mL)
was refluxed for 12 h, the nanoparticleswere then separatedmine ligand@SiO2@Fe3O4.
Fig. 4. The magnetic curves of Fe3O4 (upper) and Cueimine ligand@SiO2@Fe3O4 (lower).
A. Shouli et al. / C. R. Chimie 20 (2017) 765e772 769using an external magnet, and the residue was analyzed by
atomic adsorption spectroscopy. It was found that only a
negligible amount of copper (<1 ppm) was leaching.
The synthesis of 4g was selected as the model for
reusability test. It was performed for five consecutive runs.
On each run, the reaction was allowed to proceed to com-
plete conversion. The catalyst was carefully separated and
washed with EtOAc after the completion of reaction. Theresults showed that the reaction time increased with a
gentle slope from 8:150 to 8:450 h (Fig. 5).
In conclusion, we have developed an efficient method of
using a multicomponent reaction to synthesize propargyl-
amine derivatives with good to high yields. The reaction
was catalyzed by a novel magnetite-supported copper
nanoparticle under solvent-free conditions. The catalyst
was recovered from the reaction medium using an external
Table 1
Scope of the synthesis of propargylamines catalyzed by Cu(II)eimine ligand@SiO2@Fe3O4.
A. Shouli et al. / C. R. Chimie 20 (2017) 765e772770
Fig. 5. Reusability studies.
A. Shouli et al. / C. R. Chimie 20 (2017) 765e772 771magnet and reused for five runs with acceptable catalytic
activity.
Acknowledgments
We gratefully acknowledge the financial support of the
Mahshahr Branch, Islamic Azad University. We are also
grateful to Prof. Paula S. Branco of the New University of
Lisbon for her helpful comments.
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Copper(II) chelate-bonded magnetite nanoparticles: A new magnetically retrievable catalyst for the synthesis of propargylamines

Mohamed El Hafi

Mohammed Naas

Mohammed Loubidi

Jabrane Jouha

Youssef Ramli

Joel T. Mague

El Mokhtar Essassi

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Palladium-catalyzed regioselective direct CH arylation of pyrazolo[3,4-<i>d</i>]pyrimidines

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Amandine Baudry

Christian Bruneau

Thierry Renouard

First elaboration of an olefin metathesis catalytic membrane by grafting a Hoveyda–Grubbs precatalyst on zirconia membranes

Editorial Board - English

Ioana Fechete

Hermann Emil Fischer – The most outstanding chemist in history

Pascal Granger

Francine Agbossou

Marc J. Ledoux

C. R. Chimie 19 (2016) 1150e1151
lable at ScienceDirectContents lists avaiComptes Rendus Chimie
www.sciencedirect.comForeword/Avant-proposCatalysis: From academic research to industrial applicationsForeword
This thematic issue entitled Catalysis: From academic
research to industrial applications is a tribute to Edmond
Payen, Emeritus Professor at the National Graduate School
of Engineering Chemistry of Lille, founder and Director of
the Catalysis and Solid State Chemistry Laboratory of Lille
(UCCS) from 2006 to 2009.
As a matter of fact, this tribute includes two events. The
first one took place on 22 May 2015, with a special sci-
entific day gathering renowned researchers e Prof. Israel
Wachs, from Lehig University (USA), Prof. Krijn de Jong,
Utrecht University (The Netherlands), and Dr. Valerie
Briois, SOLEIL Synchrotron, Saclay (France) e, and
outstanding people coming from industry in close
connectionwith academiaeDr. Jean-Luc Dubois, Scientific
Director Arkema, Paris (France), Dr. Jean-Pierre Dath
(Raffinage-Chimie, “Direction strategie, developpement
recherche Total Feluy” (Belgium), and Dr. Antoine Daudin,
“IFP Energies nouvelles” (France). The scientific content of
that day tackled important academic and practical issues
reflecting the main concerns that governed the scientific
career of Edmond and are still a matter of interest today,
considering the gap between academia and industry. In
other words, this could be summarized through a key
question: how is it possible to implement fundamental
research methodologies in order to properly answer in-
dustrial practical issues?
Since the construction of the first industrial plant for
ammonia synthesis over iron-based catalysts at the
beginning of the 20th century, catalysis, and more partic-
ularly heterogeneous catalysis (but not only), has largely
contributed to the development of chemical processes,
becoming more efficient for the transformation of natural
resources and especially fossils for the production of fuels
and chemical intermediates.
Successful achievements were obtained through the
introduction of solid catalysts inside reactors capable of
working under severe operating conditions, sometimes at
very high pressure. Unfortunately, these successes
remained “enigmatic” for a long time, the catalytichttp://dx.doi.org/10.1016/j.crci.2016.08.004
1631-0748/© 2016 Académie des sciences. Published by Elsevier Masson SAS.
creativecommons.org/licenses/by-nc-nd/4.0/).reactor being usually considered as a black box, but
fortunately efficient. The understanding of the catalyst's
behaviour changed deeply with the emergence of new
theories and the development of new spectroscopic and
microscopic tools. At the end of the 1980s, the concerns of
academia and industry converged with the expectation
that a better description of catalysts and chemical pro-
cesses taking place at their surface could potentially help
in their optimization. Suddenly, industry was ready to
understand how a catalyst can run at nanoscales if po-
tential gain in activity, selectivity, and durability could be
envisioned.
It is clear that the introduction of novel characterization
techniques capable of probing the surface of catalysts at
different scales under working conditions, sometimes
mimicking those encountered in industrial catalytic pro-
cesses, largely contributes to get a deeper insight into the
nature of active sites at the surface, the nature of in-
termediates and elementary steps involved at the surface of
a solid catalyst. Nowadays, microscopic and spectroscopic
techniques allow a better description. However, a good
interpretation provided by the response given by these
techniques needs virtuosity sometimes, and one has to say
that in spite of the huge number of technological advances,
numerous challenges remain.
Today, we have to face the energy transition with the
use of carbon renewable sources: how to replace fossil re-
sources with more friendly ones to improve air quality,
especially by lowering the emission of greenhouse gases,
and to ameliorate the yields, thus minimizing the produc-
tion of wastes? New perspectives arise with the emergence
of biomass, but they imply smart catalytic formulations
more complex in their optimization.
It is clear that the UCCS deeply appreciated the dedi-
cated efforts of Edmond Payen to facilitate their entry into
this new era, anticipating and stimulating the development
of new methodologies to investigate the catalysts under
running conditions thanks to the utilization of spectro-
scopic tools of high technicality and convincing industry
that this can produce added values if they are enough
patient.This is an open access article under the CC BY-NC-ND license (http://
Foreword/Avant-propos / C. R. Chimie 19 (2016) 1150e1151 1151The second step of our tribute represents in fact a
continuation of the first one, but with the aim of offering
Edmond Payen a kind of a gift, andwewould like towarmly
thank the Editorial Committee of the journal Comptes
rendus Chimie, who supported our project with this the-
matic issue. The idea to make this a reality seemed obvious
at the end of the successful scientific day that was held in
Lille, gathering more than one hundred participants to this
friendship event, most of them coming from diverse loca-
tions in France and having developed and maintained
friendly and professional relationships with Edmond.
Based on that, there was a growing expectation to invite
Edmond's colleagues to contribute to this thematic issue,
especially those from abroad, who could not participate in
the scientific day. In the frame of these celebrations, we
conserved the same title, Catalysis: From academic research
to industrial applications.
Different topics have been selected (i) catalysis for en-
ergy, (ii) biomass conversion, (iii) environmental catalysis,
(iv) catalyst preparation and related characterization, and
(v) development of spectroscopic tools for in situ or oper-
ando investigations of catalytic reactions. Twenty papers
will have been published in this issue, coming from
Romania, Japan, Argentina, Brazil, Greece, India, Russia, and
of course France, dealing with the conversion of biomass
for the production of chemicals and biofuels, the synthesis
of catalysts for oxidative and hydrotreating reactions
including the use of heteropolyanions, environmental
catalysis with NOx removal and production of more friendlysulphur-free fossil fuels, as well as ex situ or in situ char-
acterization through resonance Raman spectroscopy, near-
ambient pressure XPS, and a quick EXAFS experiment.
Finally, an article dedicated to theoretical calculation
completes this series, covering an important topic earlier
developed at UCCS by Edmond Payen.
Wewould like towarmly thank all the contributors who
participated in the scientific day, and more specifically in
this special issue, through writing something for Edmond.
Pascal Granger*
Universite de Lille Sciences et Technologies, Unite de catalyse
et de chimie du solide, UMR 8181, bâtiment C3,
59650 Villeneuve-d'Ascq, France
Francine Agbossou
Ecole nationale superieure de chimie de Lille, Unite de
catalyse et de chimie du solide, UMR 8181, avenue
Mendeleïev, CS 90108, 59652 Villeneuve-d'Ascq cedex, France
Marc J. Ledoux
Institut de chimie et procedes pour l'energie, l'environnement
et la sante (ICPEES), ECPM, Universite de Strasbourg, 25, rue
Becquerel, 67087 Strasbourg cedex 2, France
 Corresponding author.
E-mail address: pascal.granger@univ-lille1.fr
Available online 17 September 2016


Catalysis: From academic research to industrial applications

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