Synthesis, characterization and catalytic properties of a copper complex containing decavanadate nanocluster, Na2[Cu(H2O)6]2{V10O28}·4H2O

Article abstract of DOI:10.1016/j.inoche.2017.02.001

A copper complex containing decavanadate nanocluster, Na₂[Cu(H₂O)₆]₂{V₁₀O₂₈}·4H₂O, was prepared by reaction of Cu(NO₃)₂·4H₂O and NH₄VO₃ in an aqueous solution at pH = 4 and its structure was characterized using IR, CV and X-ray crystallography. It was found to be a highly efficient and effective catalyst for the azide alkyne cycloaddition and one-pot three-component (A³) coupling of aldehydes, amines, and alkynes to produce 1,2,3-triazoles and propargylamines respectively in high yields without any co-catalyst or activator.

Full text of DOI:10.1016/j.inoche.2017.02.001

Accepted Manuscript
Synthesis, characterization and catalytic properties of a copper
complex
containing
decavanadate
nanocluster,
Na2[Cu(H2O)6]2{V10O28}·4H2O
Mojtaba Amini, Mohammad Nikkhoo, Sajjad Bahadori
Tekantappeh, S. Morteza F. Farnia, Ghodrat Mahmoudi, Orhan
Büyükgüngör
PII:
S1387-7003(17)30047-3
doi: 10.1016/j.inoche.2017.02.001
INOCHE 6550
DOI:
Reference:
To appear in:
Inorganic Chemistry Communications
Received date:
Revised date:
Accepted date:
12 January 2017
6 February 2017
9 February 2017
Please cite this article as: Mojtaba Amini, Mohammad Nikkhoo, Sajjad Bahadori
Tekantappeh, S. Morteza F. Farnia, Ghodrat Mahmoudi, Orhan Büyükgüngör , Synthesis,
characterization and catalytic properties of a copper complex containing decavanadate
nanocluster, Na2[Cu(H2O)6]2{V10O28}·4H2O. The address for the corresponding
author was captured as affiliation for all authors. Please check if appropriate.
Inoche(2017), doi: 10.1016/j.inoche.2017.02.001
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ACCEPTED MANUSCRIPT
Synthesis, characterization and catalytic properties of a copper complex
containing decavanadate nanocluster, Na [Cu(H O) ] {V O }∙4H O
2
2
6 2
10 28
2
a
a,b
a
*b
Mojtaba Amini, Mohammad Nikkhoo, Sajjad Bahadori Tekantappeh, S. Morteza F. Farnia,
a
c
Ghodrat Mahmoudi, Orhan Büyükgüngör
a
Department of Chemistry, Faculty of Science, University of Maragheh, Maragheh, Iran.
b
Department of Chemistry, University of Tehran, Tehran, Iran
c
Department of Physics, Faculty of Arts and Sciences, OndokuzMayis University, 55139 Kurupelit,
Samsun, Turkey
Abstract
A copper complex containing decavanadate nanocluster, Na [Cu(H O) ] {V O }∙4H O, was
2
2
6 2
10 28
2
prepared by reaction of Cu(NO ) ∙4H O and NH VO in an aqueous solution at pH=4 and its
3
2
2
4
3
structure was characterized using IR, CV and X-ray crystallography. It was found to be a highly
efficient and effective catalyst for the azide alkyne cycloaddition and one-pot three-component
3
(
A ) coupling of aldehydes, amines, and alkynes to produce 1,2,3-triazoles and propargylamines
respectively in high yields without any co-catalyst or activator.
3
Keywords: Nanocluster; Decavanadate; Copper; azide- alkyne cycloaddition; A - coupling
Polyoxovanadates (POVs) have been attracting considerable attention due to their applications in
medicine, biology, materials science and catalysis [1-6]. Among the different polyoxovanadates,
6
-
the decavanadate anion {V O } is one of the widely studied species which has been isolated
1
0
28
and characterized with numerous cations for antibacterial, antidiabetes and catalytic activities [7-
7].
1
The 1,2,3-triazoles and propargylamines are heterocyclic molecules that have attracted interest
due to their various applications in different fields of polymer & material science for the
*
Corresponding authors; Tel.: +98 41 37278900; Fax: +98 41 37276066. Email address: mamini@maragheh.ac.ir
1

ACCEPTED MANUSCRIPT
development of new drugs, biodegradable polymers, energetic binders and biomedical
compounds [18-23]. The copper-catalyzed azide alkyne cycloaddition reaction and three-
component coupling of aldehydes, amines, and alkynes is one of the most important reactions for
the preparation of 1,2,3-triazoles and propargylamines [23-27].
Herein we report synthesis and characterization of a novel copper complex containing
decavanadate cluster, Na [Cu(H O) ] {V O }∙4H O [28] as a highly-efficient catalyst for the
2
2
6 2
10 28
2
3
cycloaddition reaction of azides with alkynes [29] and A - coupling of aldehydes, amines, and
alkynes [30] without the need of an additional co-catalyst or reducing agent.
Copper complex containing decavanadate cluster, Na [Cu(H O) ] {V O }∙4H O (1), was
2
2
6 2
10 28
2
characterized by elemental analysis and IR spectroscopy. Crystallographic data and structural
refinements for crystals of Na [Cu(H O) ] {V O }∙4H O are summarized in Table 1. The
2
2
6 2
10 28
2
single crystal X-ray diffraction analysis shows that the asymmetric unit of 1 consists of one
-6
2+
crystallographically independent decavanadate anion{V O } , two [Cu(H O) ] cations, two
1
0
28
2
4
Na+ ions and four H O molecules. As shown in Fig. 1, the decavanadate anion consists of ten
2
edge-sharing {VO6}octahedra generated from a closed-packed aggregation of 10 vanadium and
2
8 oxygen atoms, in which the oxygen atoms exhibit terminal, μ , μ and μ coordination modes
2 3 6
with the bond lengths and angles identical to those found in the literature. Negative charge of the
-6
+
2+
decavanadate anion {V O } is neutralized by Na and [Cu(H O) ] cations. Both the
1
0
28
2
4
decavanadate anion and copper complex cations lie on inversion centers. The cationic
2
+
[
Cu(H O) ] complex possesses a typical ‘‘the Jahn-Teller distorted octahedral, four short bonds
2 6
of the water molecules (the average value dCu−O = 1.075(3)-1.090(3) Å) and two long bonds of
the water molecules (dCu−O= 1.095(3)-2.126(3) Å). The unit cell content in the crystal structure of
Na [Cu(H O) ] {V O }∙4H O, along the c-axis is shown in Fig. 2.
2
2
6 2
10 28
2
2

ACCEPTED MANUSCRIPT
Fig. 1 Ball-and-stick representation the crystals Na [Cu(H O) ] {V O }∙4H O showing the
2
2
6 2
10 28
2
atom labeling scheme.
3

ACCEPTED MANUSCRIPT
Fig. 2 View of the unit cell content in the crystal structure of Na [Cu(H O) ] {V O }∙4H O,
2
2
6 2
10 28
2
along the c-axis (yellow= Mo, purple= Cu, green= Na, red= O and gray= H).
Table 1. Crystal data and structure refinement for Na [Cu(H O) ] {V O }∙4H O
2
2
6 2
10 28
2
1
Empirical formula
Formula weight (g/mol)
Cu2 H32 Na2 O44 V10
1418.74
Temperature (K)
Wavelength(Å)
Crystal system
296
CuKα (λ = 0.71073)
triclinic
Space group
P -1
Unit cell dimensions(Å/°)
a= 8.8563(16, b= 10.9036(19, c=11.1370(18)
α= 64.781(5), β= 74.971(5), γ= 70.830(6)
3
Volume(Å )
910.0(3)
1
2.589
11.958
3000.0
Z
3
Density (calculated) (g/cm )
Absorption coefficient (mm )
F(000)
-
1
3
Crystal size (mm )
Theta range for data
0.199 × 0.105 × 0.066
6.19 to 152.182
4

ACCEPTED MANUSCRIPT
collection
Index ranges
-16 ≤ h ≤ 12, -28 ≤ k ≤ 26, -22 ≤ l ≤ 23
50075
Reflections collected
Independent reflections
Refinement method
11267 [Rint = 0.0991, Rsigma = 0.0945]
2
Full-matrix least-squares on F
Data / restraints / parameters
11267/24/694
2
1.040
Goodness-of-fit on F
Final R indices [I>2sigma(I)]
R indices (all data)
R1 = 0.0779, wR2 = 0.1974
R1 = 0.1169, wR2 = 0.2433
-
-3
Largest diff. peak and hole(Å
1.67/-1.03e Å
3
)
-1
The study of the electrochemical response of 1 (0.5 mM L ) was carried out in the range of -0.6
to +1.0 V at room temperature with a Ag/AgCl as the reference electrode in the presence of 0.2
M electrolyte Na SO -H SO . By comparison of the redox properties of the two nanoclusters
2
4
2
4
Na [Cu(H O) ] {V O }∙4H O and Na {V O }, the redox peak I-I' can be attributable to the
2
2
6 2
10 28
2
6
10 28
2
+
redox of Cu (Fig. 3a) [31]. Fig. 3b shows cyclic voltammograms of 1 at different times. It was
clearly seen that due to absorption of the copper on the electrode with increasing time, the redox
2
+
peaks of Cu increased.
Fig. 3 CV of a) nanoclusters Na [Cu(H O) ] {V O }∙4H O and Na {V O } in H O at a scan
2
2
6 2
10 28
2
6
10 28
2
-1
rate of 50 mV s ; b) nanocluster Na [Cu(H O) ] {V O }∙4H O at different times
2
2
6 2
10 28
2
The catalytic performance of the copper complex containing decavanadate cluster,
Na [Cu(H O) ] {V O }∙4H O was investigated for the 1,3‐dipolar cycloaddition reaction.
2
2
6 2
10 28
2
Phenylacetylene, benzyl chloride and NaN was selected as the model substrates for optimization
3
of reaction conditions (Table 2).
The 1,3‐dipolar cycloaddition reaction between
5

ACCEPTED MANUSCRIPT
phenylacetylene, benzyl chloride and NaN did not work in the absence of catalyst (entry 1).
3
First, the catalyst loading was screened and 0.42 mol% loading had the highest yield (97%) after
1
2 h of stirring (entries 2, 3). Noteworthy, the catalytic activity of the system reduced
significantly when 1 was replaced by Na {V O }, Cu(NO ) ∙4H O and mixture of Na {V O }
6
10 28
3 2
2
6
10 28
and Cu(NO ) ∙4H O and the product was respectively obtained in 0%, 74% and 70% yields.
3
2
2
Different solvents were then screened and it was found that H O was the most suitable solvent
2
for cycloaddition reaction. The reaction had poor yields by using acetonitrile, toluene, acetone,
ethanol or methanol as a solvent due to the the poor solubility of NaN (entries 3–8). As shown
3
in Table 2, a higher yield of 1,4‐diphenyl triazole product is obtained with increasing the reaction
temperature to 70°C (entries 9, 10) and increasing reaction time to 12 hours (entries 11−13).
Table 2.The effect of various conditions on the azide–alkyne cycloaddition
Entry
Catalyst amount
Solvent Temperature Time Yield
a
(
Mol %)
(°C)
70
70
70
70
70
70
70
70
r.t.
50
70
70
70
(h)
12
12
12
12
12
12
12
12
12
12
2
(%)
0
78
98
-
-
3
6
8
30
94
7
55
98
1
2
3
4
5
6
7
8
9
-
H O
2
0.14
0.42
0.42
0.42
0.42
0.42
0.42
0.42
0.42
0.42
0.42
0.42
H O
2
H O
2
CH CN
3
toluene
acetone
C H OH
2
5
CH OH
3
H O
2
1
1
1
1
0
1
2
3
H O
2
H O
2
H O
8
12
2
H O
2
a
Isolated yield.
Next, the CuAAC click reactions between various bezyl halides and alkynes were explored under
the optimal conditions (Table 3). Cycloaddition of phenylacetylene with benzyl halides showed
the highest reactivity than other alkynes 2-methyl-3-butyn-2-ol and 4-tert-butylphenylacetylene
and their corresponding triazoles were obtained in 89−97% yields (entries 1-4 and 7).
Noteworthy is that the catalytic activity is not greatly influenced by the presence of an electron
donating or electron withdrawing groups on the phenyl ring of the benzylhalides (entries 2-4).
Benzyl bromide also showed excellent reactivity in cycloaddition with phenylacetylene and 4-
tert-butylphenylacetylene, giving 97% and 91% yields respectively (entries 7 and 8).
6

ACCEPTED MANUSCRIPT
Table 3. Cycloaddition of benzyl halides with terminal alkynes in the presence of
Na [Cu(H O) ] {V O }∙4H O
2
2
6 2
10 28
2
Entry
1
Benzyl halide
Alkyne
Yield (%)
98
Cl
2
3
97
91
Cl
Cl
NO2
4
5
6
7
8
Cl
89
72
86
97
91
O N
2
Cl
Cl
HO
Br
Br
3
The catalytic potential of Na [Cu(H O) ] {V O }∙4H O was also studied for A - coupling of
2
2
6 2
10 28
2
aldehydes, secondary amines and terminal alkynes to afford the corresponding propargylamines.
To study the optimized reaction conditions, a model reaction of benzaldehyde, piperidine and
phenylacetylene was performed using 0.005g of 1 in the presence of various solvents at 100 °C
to afford the corresponding propargylamines as shown in Table 4. In the presence of organic
solvents such as CHCl , CH CN and propanol, the product was obtained in 54−75% yields
3
3
(
entries 3−5). A trace amount of product was formed in water or ethanol as a solvent (entries 6,
), but in the presence of toluene, the desired product was obtained in 81% yield (entry 2). The
effect of temperature, reaction time and amount of catalyst on the product yield was also studied
7
(entries 8−11). The results revealed that the usage of 0.7 Mol
%
of
7

ACCEPTED MANUSCRIPT
Na [Cu(H O) ] {V O }∙4H O at 100 °C for 12 h was the best condition to obtain the
2
2
6 2
10 28
2
tetrasubstituted propargylamine in 81% yield (entry 2).
3
Table 4.The effect of various conditions on the A coupling of aldehyde, alkyne and amine
Entry
Catalyst amount
Solvent Temperature Time Yield
a
(
Mol %)
(°C)
100
100
reflux
reflux
reflux
reflux
reflux
100
(h)
12
12
12
12
12
12
12
12
12
12
12
(%)
0
1
2
3
4
5
6
7
8
9
-
toluene
toluene
CHCl3
0.7
0.7
0.7
0.7
0.7
0.7
0.42
1.0
0.7
0.7
81
75
64
54
21
10
59
75
16
19
CH CN
3
propanol
H O
2
C H OH
2
5
toluene
toluene
toluene
toluene
100
r.t
50
1
1
0
1
a
Isolated yield.
The general versatility of catalyst was studied for the synthesis of tetrasubstituted
propargylamines from the reaction among various aldehydes such as benzaldehyde, pyrrole-2-
carboxaldehyde, furfural and secondary amines including piperidine, morpholine and alkynes
such as phenylacetylene and propargyl alcohol under optimized reaction conditions (Table 5).
Almost all screened substrates underwent the three-component coupling reactions smoothly to
afford the corresponding products in 42−90% yields as summarized in Table 2. However, the
reaction proceeded slowly in the coupling of morpholine with pyrrole-2-carboxaldehyde and
furfural (entries 6, 7). In the coupling with aliphatic alkyne, propargyl alcohol, piperidine gave
lower yield than morpholine (entry 8, 9).
3
Table 5. Synthesis of propargylamines by the A coupling of aldehyde, alkyne and amine
NR R4
3
catalyst
3
R NHR4
2
R1
+
R CHO +
o
toluene, 100 C, 12 h
R2
R1
Entry
Aldehyde
Amine
Alkyne
Yield
8

ACCEPTED MANUSCRIPT
1
2
81
76
CHO
N
H
H
N
CHO
N
H
3
4
O
80
90
CHO
CHO
N
H
O
N
H
O
5
6
H
N
60
60
CHO
N
H
O
O
CHO
CHO
N
H
7
8
42
80
OH
OH
N
H
O
CHO
N
H
We report successful preparation of a novel copper complex containing decavanadate cluster,
Na [Cu(H O) ] {V O }∙4H O by simple reaction of Cu(NO ) ∙4H O and NH VO in an
2
2
6 2
10 28
2
3 2
2
4
3
aqueous solution at pH=4. A new approach to the azide alkyne cycloaddition and one-pot three-
3
component (A ) coupling of aldehydes, amines, and alkynes was developed using
Na [Cu(H O) ] {V O }∙4H O as a catalyst. Various kinds of substrates were successfully
2
2
6 2
10 28
2
reacted to their corresponding 1,2,3-triazoles and propargylamines in a timely manner.
The advantage of the present method is the use of a chemically stable catalyst, highly efficient
3
azide alkyne cycloaddition and A -coupling reactions in good to excellent yields and lack of co-
catalyst and reducing agents in the reactions.
9

ACCEPTED MANUSCRIPT
Supplementary Data
The CIF file of crystal structure nanocluster, Na [Cu(H O) ] {V O }∙4H O has been deposited
2
2
6 2
10 28
2
with the CCDC, No. 1510169. This data can be obtained free of charge via
http://www.ccdc.cam.ac.uk/conts/retrieving.html, or from the Cambridge Crystallographic Data
Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail:
deposit@ccdc.cam.ac.uk
Acknowledgments
Partial funding support was provided by the Research Council of University of Maragheh (M.A.)
and Tehran University (S.M.F.). Also the authors acknowledge Scientific and Technological
Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker
D8 QUEST diffractometer.
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28] Preparation of nanocluster Na [Cu(H O) ] {V O }∙4H O (1): Cu(NO ) ∙4H O
2
2
6 2
10 28
2
3 2
2
(
4 mmol) was added to an aqueous solution (20 mL) of NH VO (1 mmol) with stirring
4 3
to form a homogenous mixture. The pH of the solution was adjusted to 4 by a 5M
aqueous HCl solution, and the stirring was continued for 1 h, giving a stable green color
solution, which was left standing under air in a beaker at room temperature to form green
crystals.
[
29]
General procedure for the azide–alkyne cycloaddition: Alkyne (0.5mmol), the
organic halide (0.55mmol) and NaN (0.55mmol) were added to a solution of
3
Na [Cu(H O) ] {V O }∙2H O in 2 mL of H O. The reaction mixture was warmed to 70
2
2
6 2
10 28
2
2
°
C and monitored by TLC until total conversion of the starting materials. After addition
of 5 mL of water, the resulting mixture was extracted with EtOAc (2× 10 mL). The
collected organic phase was dried with anhydrous CaCl and the solvent was removed to
2
give the corresponding triazoles, without requirement of further purification.
3
[
30]
General procedure for the A - coupling reaction: The aldehyde (0.5 mmol), amine
(
0.5 mmol), alkyne (0.55 mmol), 2 mL of toluene and Na [Cu(H O) ] {V O }∙4H O
2
2
6 2
10 28
2
catalyst (0.7 Mol%) were stirred at 100 °C for 12 h. After completion of the reaction,
with addition of 5 mL of water, the resulting mixture was extracted with EtOAc (2× 10
mL). The collected organic solvent was removed using a rotary evaporator to give the
corresponding propargylamines, without further purification.
[
31]
B. Keita, E. Abdeljalil, L. Nadjo, R. Contant, R. Belghiche, Langmuir 2006, 22,
0416-10425.
1
1
2

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Graphical abstract
3
The azide alkyne cycloaddition and one-pot three-component (A ) coupling of aldehydes,
amines, and alkynes to produce 1,2,3-triazoles and propargylamines respectively were conducted
by a novel copper complex containing decavanadate cluster, Na [Cu(H O) ] {V O }∙4H O.
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10 28
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ACCEPTED MANUSCRIPT
Highlights
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. A novel copper complex containing decavanadate cluster, Na [Cu(H O) ] {V O }∙4H O is
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6 2 10 28
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synthesized.
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. The polyoxovanadate is applied for the azide–alkyne cycloaddition and A -coupling reactions.
. Excellent yield has been achieved.
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