Copper-polymer nanocomposite: An efficient catalyst for green Huisgen click synthesis

Article abstract of DOI:10.1016/j.tetlet.2018.03.028

A new method for Huisgen [3+2] cycloaddition synthesis of 1,4- and 1,4,5-substituted-1H-1,2,3-triazoles was reported. The reaction was catalyzed by the product of thermolysis of copper (II) poly-5-vinyltetrazolate. Heterogeneous catalyst includes copper nanoparticles which supported on polymeric matrix. It presents recovered and recycled catalyst and the catalyzed reaction proceeds in aerobic conditions at room temperature in aqueous media.

Full text of DOI:10.1016/j.tetlet.2018.03.028

Accepted Manuscript
Copper-polymer nanocomposite: an efficient catalyst for green Huisgen click
synthesis
Alexander V. Zuraev, Yuri V. Grigoriev, Vladislav A. Budevich, Oleg A.
Ivashkevich
PII:
S0040-4039(18)30325-3
https://doi.org/10.1016/j.tetlet.2018.03.028
TETL 49797
DOI:
Reference:
Tetrahedron Letters
To appear in:
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Revised Date:
Accepted Date:
31 January 2018
4 March 2018
11 March 2018
Please cite this article as: Zuraev, A.V., Grigoriev, Y.V., Budevich, V.A., Ivashkevich, O.A., Copper-polymer
nanocomposite: an efficient catalyst for green Huisgen click synthesis, Tetrahedron Letters (2018), doi: https://
doi.org/10.1016/j.tetlet.2018.03.028
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A new method for Huisgen [3+2] cycloaddition synthesis of
Copper-polymer nanocomposite: an efficient
catalyst for green Huisgen click synthesis
1,4- and 1,4,5-substituted-1H-1,2,3-triazoles was reported.
The reaction was catalyzed by the product of thermolysis of
copper (II) poly-5-vinyltetrazolate. Heterogeneous catalyst
includes copper nanoparticles which supported on polymeric
matrix. It presents recovered and recycled catalyst and the
catalyzed reaction proceeds in aerobic conditions at room
temperature in aqueous media.
Alexander. V. Zuraev*,
Yuri. V. Grigoriev,
Vladislav A. Budevich,
Oleg. A. Ivashkevich*

1
Tetrahedron Letters
journal homepage: www.els evier.com
Copper-polymer nanocomposite: an efficient catalyst for green Huisgen click
synthesis
Alexander V. Zuraeva, b, ∗, Yuri V. Grigorieva, Vladislav A. Budevichb and Oleg A. Ivashkevichb
aResearch Institute for Physical Chemical Problems of Belarusian State University, Leningradskaya 14, 220006 Minsk, Belarus
bBelarusian State University, Nezalezhnastsi avenue 4, 220050 Minsk, Belarus
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
A new method for Huisgen [3+2] cycloaddition synthesis of 1,4- and 1,4,5-substituted-1H-1,2,3-
triazoles was reported. The reaction was catalyzed by the product of thermolysis of copper (II)
poly-5-vinyltetrazolate. Heterogeneous catalyst includes copper nanoparticles which supported
on polymeric matrix. It presents recovered and recycled catalyst and the catalyzed reaction
proceeds in aerobic conditions at room temperature in aqueous media.
Available online
2018 Elsevier Ltd. All rights reserved.
Keywords:
1,2,3-1H-Triazoles
Copper nanoparticles
Poly-5-vinyltetrazole
Huisgen-click reaction
Alkynes
1,2,3-Triazoles are basically five-membered nitrogen
heterocyclic compounds. They have tremendous application in
various research fields, including material chemistry,1 polymer
chemistry,1 synthetic organic chemistry,2 medicinal chemistry3
and pharmaceutical synthesis4. In addition, 1,2,3-triazoles are
important privileged scaffolds with a wide range of biological
activities, such as anti-viral, hypoallergic and anti-cancer.4 The
classical method for synthesis of 1,2,3-triazole derivatives is the
Huisgen [3+2] cycloaddition reaction between the terminal
alkynes and azides.5-7 In 2002, the first copper(I)-catalyzed azide-
alkyne cycloaddition (CuAAC) was discovered independently by
the groups of Sharpless8 and Meldal,9 by whom 1,4-disubstituted-
1H-1,2,3-triazoles were prepared regioselectively under mild
conditions.10 Until now, a number of CuAAC procedures have
been developed including the use of Cu(II) complexes11-13, Cu(I)
complexes,14 and Pd-containing complexes15. Above mentioned
catalytic systems are highly efficient, but sometimes these
reagents are far more expensive. However, the use of such
catalyst entailes some drawbacks such as the need for high
temperature, and in some cases the lack of recyclability of the
catalyst. Therefore, although many effective catalysts for
Huisgen [3+2] cycloaddition reaction are already known, the
search for alternative, recyclable and less expensive catalysts
remain relevant.
The present work is devoted to catalytic Huisgen [3+2]
cycloaddition synthesis of 1,4- and 1,4,5-substituted-1H-1,2,3-
triazoles. To date, many catalytic systems have been proposed for
Huisgen [3+2] cycloaddition reaction, however most of them are
not reusable and quite expensive. Taking into account these
circumstances, herein we focused our attention on the catalytic
synthesis of 1,4- and 1,4,5-substituted-1H-1,2,3-triazoles using
our nanocopper-based heterogeneous catalyst. The possibility to
be reusable makes the heterogeneous catalyst even cheaper.
As the catalyst for 1,3-dipolar cycloaddition reaction between the
terminal alkynes, sodium azide and benzyl chloride (Scheme 1a)
(hereinafter referred to as Pathway 1) and for the reaction
between alkynes and aryl azide (Scheme 1b) (hereinafter referred
to as Pathway 2), we used the product of thermolysis of
copper(II) poly-5-vinyltetrazolate (hereinafter referred to as Cu-
Pol) (Scheme 1).
According to our previous work, the Cu-Pol catalyst was
obtained by thermolysis of copper(II) poly-5-vinyltetrazolate
with copper content equal to 53.57 wt.%.16
Noteworthy, that copper nanoparticles (hereinafter referred to
as Cu NPs), supported on polymer matrix, are resistant to
oxidation on air and water action. Hence, polymer matrix
increases the stability of the particles by altering their inherent
sensitivity to oxygen and water.16
———
∗ Corresponding author. Tel.: +375-44-534-23-76; e-mail: zuraev@bsu.by

2
Tetrahedron
In case of pathways 1 and 2 (Scheme 1) high catalytic activity
of Cu–Pol nanocomposite is explained by its high dispersity in
water and interaction of organic reactants with Cu NPs attached
to polymeric matrix. During the reaction, the hydrophobic nature
of polymeric matrix surface allows the phenylacetylene and
benzyl azide (it is formed at the interface) to interact on the
surface of polymeric matrix thereby increasing the yields of (1a)
(Scheme 2). 16
Next, the model reaction was performed at room temperature
catalyzed by different amounts of Cu-Pol nanocomposite. As
shown in Table 2 (Entries 1–4), the model reaction could still
finish in 3 h, when catalyzed by 5-11 mol-% Cu-Pol with almost
the same yields as that when catalyzed by 18 mol-%. However, a
further decrease of the loading of Cu-Pol nanocomposite (Entries
5-9) led to a long reaction time.
Table 2. Different amounts of Cu–Pol nanocomposite catalyst
in synthesis of (1a)a by pathway 1
Catalyst loading Synthesis
Isolated yield
of 1a /%
Entry
/mol-%
duration /h
Scheme 1. a) Synthesis of 1-benzyl-4-aryl-1H-1,2,3-triazoles and 1-
benzyl-4-aryl-5-(arylethynyl)-1H-1,2,3-triazoles (Pathway 1); b)
Synthesis of 1,4-diaryl-1H-1,2,3-triazoles (Pathway 2).
1
2
3
4
5
6
7
8
9
18
11
8
3
95
95
94
96
92
90
91
92
89
3
3
The obtained Cu-Pol nanocomposite was investigated as a
catalyst in Huisgen cycloaddition reaction (Scheme 1). At the
initial stage of our investigation, we effort to optimize the
catalytic reaction on the one-pot three-component cycloaddition.
We chose the reaction of synthesis of 1-benzyl-4-phenyl-1H-
1,2,3-triazole as a model (Scheme 2).
5
3
3
5
1
16
20
24
25
0.5
0.3
0.2
aUnder the conditions of Ref. 19
Scheme 2. The model reaction for catalytic activities investigation.
Our model experiments, concerned with the synthesis of (1a)
by using Cu–Pol nanocomposite catalyst, show that it can be
used as a reusable heterogeneous catalyst. Table 3 demonstrates
changes in its catalyst efficiency for eight successive cycles of
the use.
Different solvents were scanned to find their effects on the
catalytic activity of Cu-Pol in the model reaction (Table 1).
Table 1. Effects of solvents on the catalytic activity of
Cu-Pola
Table 3. Reusability of Cu–Pol nanocomposite catalyst in
synthesis of (1a)a by pathway 1
Isolated yield of 1a
/%
No. Solvent
Time/h
Cycle number
Isolated yield (%)
1
2
3
4
PhMe
THF
24
15
4.5
3
35
47
87
96
1
2
3
4
5
6
7
8
96
94
95
92
91
93
90
86
EtOH
H2O
aUnder the conditions of Ref. 19
Product (1a) was obtained in excellent yields in all protonic
solvents (Entries 3, 4) and the best result was obtained for water.
It is important that, the water belongs to green solvents. It should
been noted that by using homogeneous catalysts11-14 in Huisgen
click reactions the best results were obtained also for green
solvents (scCO2, ionic liquids, and water). Therefore, Cu-Pol
nanocomposite is highly effective catalyst for cycloaddition
reaction which proceed in preferred and suitable green solvent
like water at room temperature.
a
After completion of a previous cycle, the catalyst was recovered by a
procedure, described in Experimental Section (Ref. 20), and then used again
in the next cycle.

3
If to be limited to 90% yield of (1a) as acceptable for the
practical use, the catalytic system can be reused seven times
without considerable loss in the catalytic activity. After seven
cycles, the catalytic activity of Cu–Pol nanocomposite begins to
decrease more noticeably. We believe that the decrease in
catalytic activity is caused by the loss of copper particles from
the polymeric matrix surface, which can take place as a result of
recovery procedure as well as during liquid phase cycloaddition
synthesis. After seven cycles, copper content of nanocomposite is
about 40 wt.%.
Reusability of the catalyst is possibly due to stabilization of
catalytically active copper particles by polymeric matrix. It
should be noted that longer reaction time is practically not
required when recycled catalyst is used. Thus, the optimized
reaction conditions established, the scope of this reaction was
then evaluated with respect to various substituted terminal
alkynes. As shown in Table 4, these transformations displayed
high functional group tolerance and proved to be a general
method for the synthesis of 1,4- and 1,4,5-substituted-1H-1,2,3-
triazoles using pathways 1 or 2 respectively (Scheme 1, Figure
1). Terminal aryl or heteroaryl alkynes gave the corresponding
1,2,3-triazoles in good to excellent yields. Cu–Pol nanocomposite
heterogeneous catalyst, prepared in the present work, exhibits
certain advantages compared to early proposed catalysts for
synthesis of 1,4- and 1,4,5-substituted 1H-1,2,3-triazols. First of
all, it should be noted that most catalytic systems are
homogeneous.10-15 As a result, these catalysts despite their
effectiveness are not recyclable, that makes the synthesis more
expensive. Therefore, Cu–Pol nanocomposite is highly effective,
recyclable and inexpensive catalyst, used at low catalytic loading,
and allowing the reaction to proceed at room temperature in
water.
Figure 1. Synthesised of 1,4- and 1,4,5-substituted 1H-1,2,3-triazols.
Table 4. Synthesis of 1,4- and 1,4,5-substituted-1H-1,2,3-triazoles
Duration
of
synthesis
Isolated
yield
(%)
Entry
Alkyne
Product
/h
1a
1b
1c
1d
1e
1f
Phenylacetylene
m-Tolylacetylene
1,4-Diethynylbenzene
3-Ethynylpyridine
Phenylacetylene
m-Tolylacetylene
Phenylacetylene
m-Tolylacetylene
1-Benzyl-4-phenyl-1H-1,2,3-triazole
3
96
96
98
64
79
85
92
90
1-Benzyl-4-(m-tolyl)-1H-1,2,3-triazole
2.5
2
1-Benzyl-4-(4-ethynylphenyl)-1H-1,2,3-triazole
3-(1-Benzyl-1H-1,2,3-triazol-4-yl)pyridine
1-Benzyl-4-phenyl-5-(phenylethynyl)-1H-1,2,3-triazole
1-Benzyl-4-(m-tolyl)-5-(m-tolylethynyl)-1H-1,2,3-triazole
4-Phenyl-1-tosyl-1H-1,2,3-triazole
6
4
3.5
0.5
0.5
1g
1h
4-(m-Tolyl)-1-tosyl-1H-1,2,3-triazole
aUnder the conditions of Ref. 18 and 19
catalytic activity; b) low catalytic loading; c) easily recoverable
for further usage; d) cheapness; e) resistance to oxidation on air
and water action. By using this catalyst, Huisgen cycloaddition
reaction proceeds in aerobic conditions and without any ligands
at room temperature in water with relatively short reaction time.
Such a method is interesting as it avoids not only the use of
stabilizers, additional ligands and supports, but also the
production of harmful substances.
Conclusions
In summary, we obtained a new catalyst for synthesis of 1,4-
and 1,4,5-substituted-1H-triazoles. The catalyst presents copper
nanoparticles, supported on nitrogen-containing polymer matrix.
It demonstrated valuable catalyst qualities such as: a) high

4
Tetrahedron
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Bioorganic Chemistry NAS Belarus, Minsk) and I. P.
Edimicheva (Belarusian State University, Minsk) for the structure
verification of 1,4- and 1,4,5-substituted-1H-1,2,3-triazoles.
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wt %). The resulting solution of sodium poly-5-vinyltetrazolate
was added to aqueous solution of copper (II) nitrate (100 mL, 25
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h. After that the solution was filtered through the cellulose
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vinyltetrazolate was washed with water and ethanol, and dried in a
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water (3.0 mL). The resulting mixture was stirred at room
temperature and the reaction was monitored by gas
chromatography-mass spectrometry (GC-MS) until the starting
reagents disappeared. After the completion of the reaction, the
mixture was filtered, and the mother solution was extracted with
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Alkyne (1.0 mmol), sodium azide (1.2 mmol), benzyl chloride (1.0
mmol) and Cu–Pol nanocomposite (4.7 mg, 0.5 mol-%) were
suspended in deionized water (3.0 mL). The resulting mixture was
stirred at room temperature and the reaction was monitored by gas
chromatography-mass spectrometry (GC-MS) until the starting
reagents disappeared. After the completion of the reaction, the
mixture was filtered, and the mother solution was extracted with
ethyl acetate. The organic layer was dried with anhydrous sodium
sulfate, and the solvent was evaporated to give the corresponding
triazoles, which were purified by column chromatography
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5
• A new method for Huisgen [3+2]
cycloaddition synthesis of 1,4- and
1,4,5-substituted-1H-1,2,3-triazoles
was reported.
• Heterogeneous catalyst includes
copper nanoparticles which supported
on polymeric matrix was obtained.
• Structures were elucidated on the
basis of NMR and GC-MS analysis.