Preparation of aryl azides of aryl boronic acids and one-pot synthesis of 1,4-diaryl-1,2,3-triazoles by a magnetic cysteine functionalized GO–CuI/II nanocomposite

Article abstract of DOI:10.1002/aoc.5789

A mixed Cu^I/Cu^IIcatalyst based on magnetic cysteine functionalized graphene oxide (Cu^I/II@Cys-MGO) was prepared and used for the azidonation reaction of aryl boronic acids and one-pot synthesis of 1,4-diaryl ?1,2,3-triazoles. Aryl azides were obtained in good yields and short reaction times via cross-coupling of aryl boronic acids with sodium azide in the presence of Cu^II catalytic species in this catalytic system. The azide-alkyne cycloaddition reaction was catalyzed by CuI catalytic species in Cu^I/^II@Cys-MGO nanocomposite.

Full text of DOI:10.1002/aoc.5789

Received: 17 January 2020
DOI: 10.1002/aoc.5789
Revised: 23 March 2020
Accepted: 19 April 2020
F U L L P A P E R
Preparation of aryl azides of aryl boronic acids and one-pot
synthesis of 1,4-diaryl-1,2,3-triazoles by a magnetic cysteine
functionalized GO–CuI/II nanocomposite
Fatemeh Rafiee
| Parvaneh Khavari
Department of Chemistry, Faculty of
physic-chemistry, Alzahra University,
Vanak, Tehran, Iran
A mixed CuI/CuIIcatalyst based on magnetic cysteine functionalized graphene
oxide (CuI/II@Cys-MGO) was prepared and used for the azidonation reaction
of aryl boronic acids and one-pot synthesis of 1,4-diaryl −1,2,3-triazoles. Aryl
azides were obtained in good yields and short reaction times via cross-coupling
of aryl boronic acids with sodium azide in the presence of CuII catalytic species
in this catalytic system. The azide-alkyne cycloaddition reaction was catalyzed
by CuI catalytic species in CuI/II@Cys-MGO nanocomposite.
Correspondence
Fatemeh Rafiee, Department of
Chemistry, Faculty of physic-chemistry,
Alzahra University, Vanak. Tehran, Iran,
P.O. Box: 1993893973.
Email: f.rafiee@alzahra.ac.ir
K E Y W O R D S
aryl azide, copper-catalyzed cross-coupling, functionalized graphene oxide, magnetic catalyst,
triazole
1 | INTRODUCTION
terminal alkynes.[24–26] However, this method requires
high temperature, an inert gas atmosphere, and a long
Organic azides have received considerable interest in
materials science,[1] supramolecular chemistry,[2] drug
discovery,[3] and as a photoaffinity labeling agent for
biomolecules in biochemistry.[4] They have also been
recognized as the synthetic precursors for accessing
various functional groups, such as amines,[5] amides,[6]
carbamates,[7] and aziridines,[8] and for the synthesis
of substituted 1,2,3-triazoles via azide alkyne Huisgen
cycloaddition.[9–12] The 1,2,3-triazole moiety has
attracted considerable attention because of its potential
utility in various fields. Substituted 1,2,3-triazoles
have shown wide range of biological properties
such as antibacterial,[13] antifungal,[14] antiviral,[15]
antiallergic,[16] and antitubercular.[17] Other useful
applications include pharmaceutical agents such as
tazobactam,[18] agrochemicals as plant growth retar-
dants and protection fungicides,[19] bioorthogonal
reaction time due to the slow azidonation of aryl
halides. The copper-catalyzed coupling of commercially
available arylboronic acids with azide sources have
been developed as an environmentallt friendly process
for the preparation of aryl azide derivatives.[27–31] This
method is compatible with the conditions of the
copper(I)-catalyzed
azide–alkyne
cycloaddition
(CuAAC) reaction, thus it can lead to two consecutive
reactions in the one pot. The first coupling is
done under a copper(II) catalytic cycle while the
CuAAC reaction is facilated with a copper(I) cata-
lyst.[32] At the completion of the boronic acid–azide
coupling, the addition of an alkyne and a reducing
agent such as sodium ascorbate results in a efficient
CuAAC reaction.[33] Here, we report a mixed Cu(I)/
Cu(II) composite based on magnetic cysteine
functionalized graphene oxide that efficiently catalyzes
the conversion of aryl boronic acids to aryl azides and
one-pot synthesis of 1,4-diaryl-1,2,3-triazoles.
chemistry,[20]
dyes,[21]
corrosion
inhibitors,[22]
photostabilizers, and photographic materials.[23]
The common procedure for the synthesis of
1,2,3-triazoles is copper-catalyzed in situ generation of
aryl azides from aryl halides and then reaction with
The immobilization of metal catalytic species on car-
bon base supports such as graphene and modified deriva-
tives with high surface-to-volume ratio leads to the
Appl Organomet Chem. 2020;e5789.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5789

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RAFIEE AND KHAVARI
enhancment of stability, activity and reusability, and so
reduces the overall cost of the process. Also, the interac-
tion between graphene and aromatic reactants may make
them accessible to the active sites of metal active species
and leads to acceleration in the chemical
conversion.[34,35]
2.2 | Preparation of CuI/II@Cys-MGO
nanocomposite
The CuI/II@Cys-MGO nanocomposite was prepared
according to our previous work.[36]
2.3 | General procedure for the coupling
reaction of aryl boronic acids with NaN3
2 | EXPERIMENTAL
Aryl boronic acid (0.5 mmol), NaN3 (0.6 mmol),
and CuI/II@Cys-MGO nanocatalyst (0.005 g) were added
to a round-bottomed flask containing 3 ml of EtOH:H2O
(1:1). The mixture was stirred at 60ꢀC for the time indi-
cated in Table 2. The mixture was stirred continuously
during the reaction and monitored by both TLC (n-hex-
ane–EtOAc, 7:3) and gas chromatography (GC). When
the reaction was completed, the mixture was cooled and
the catalyst separated by a magnet and the final product
purified by plate chromatography.
2.1 | Characterization techniques and
reagents
Commercial materials were purchased from Merck
(Darmstadt, Germany), Aldrich (Germany), Alfa-aeser
(Massachusetts, USA), and Exir (Austria) as analytical
grade and used without further purification. Fourier
transform infrared (FT-IR) spectra were recorded
as KBr pellets using a Bruker Tensor 27 spectrometer
in the 400–4000 cm−1 range. 1H NMR spectra were
recorded with
a
Brucker Avance 500 MHz
machine using CDCl3 as solvent and TMS as standard
sample. X-ray photoelectron spectroscopy (XPS)
analysis was done by a Thermo Scientific, ESCALAB
250 Xi Mg X-ray resource. The development of the
coupling reactions was reported using thin-layer chro-
matography (TLC) with commercial aluminum-backed
plates of silica gel 60 F254 under UV light and
an Agilent 6890 GC and GC–MS model Agilent
Series 5973.
2.4 | General procedure for the one-pot
synthesis of 1,4-diaryl-1,2,3-triazoles
To a round-bottomed flask containing aryl boronic acid
(0.5 mmol) and NaN3 (0.6 mmol) in EtOH:H2O (1:1)
(3.0 ml) was added CuI/II@Cys-MGO nanocatalyst
(0.005 g) and the mixture stirred at 60ꢀC. At completion
of the azidonation reaction, phenyl acetylene (0.55 mmol)
was added to the reaction mixture reaction and it was
FIGURE 1 XPS spectra of
CuI/II@Cys-MGO nanocatalyst

RAFIEE AND KHAVARI
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stirred at same temperature. After the reaction was com-
pleted, the catalyst was separated by an external magnet.
The residue was concentrated under reduced pressure
and purified by plate chromatography.
3 | RESULTS AND DISCUSSION
In continuation of our research on metal immobilization
on various modified supports for catalytic purposes, we
SCHEME 1 The preparation of
aryl azides and 1,4-diaryl-1,2,3-triazoles
using CuI/II@Cys-MGO nanocatalyst
TABLE 1
Optimization of reaction conditions in azidonation of 2-methoxy phenyl boronic acida
Entry
1
Solvent
Temperature (ꢀC)
Catalyst (g)
0.005
0.005
0.005
0.005
0.005
0.005
–
Time (min)
Conversion (%)
H2O
r.t.
60
r.t.
60
r.t.
60
60
60
60
60
60
60
r.t.
60
r.t.
60
r.t.
60
60
60
60
60
180
180
180
70
–
2
H2O
–
3
EtOH
50
90
80
95
–
4
EtOH
5
H2O/EtOH
H2O/EtOH
H2O/EtOH
H2O/EtOH
H2O/EtOH
H2O/EtOH
H2O/EtOH
MeOH
300
20
6
7
40
8
0.001
0.004
0.006
0.007
0.005
0.005
0.005
0.005
0.005
0.005
0.005
0.005
0.005
0.005
0.005
40
–
9
40
70
95
95
50
80
90
30
50
50
90
95
95
95
75
10
11
12
13
14
15
16
17
18
19b
20c
21d
22e
20
20
50
MeOH/H2O
MeOH/H2O
CH3CN
180
50
300
100
300
60
CH3CN
H2O/CH3CN
H2O/CH3CN
H2O/EtOH
H2O/EtOH
H2O/EtOH
H2O/EtOH
40
45
30
60
Note. r.t., room temperature.
aReaction conditions: ArB (OH)2 (0.5 mmol), NaN3 (1 mmol), nanocatalyst (g), solvent (3 ml).
bN-amidinoglycine was used as bioligand instead of cysteine.
cHystidine was used as bioligand instead of cysteine.
dTyrosine was used as bioligand instead of cysteine.
eCuI@Cys-MGO nanocomposite was used as catalyst.

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RAFIEE AND KHAVARI
TABLE 2
Cross-coupling reaction of aryl boronic acids with NaN3 catalyzed by CuI/II@Cys-MGO nanocompositea
Entry
ArB (OH)2
Product
Time (min)
Conversion (%)
Ref.
[30]
1
20
95
[30]
2
3
150
70
90
85
[37]
[38]
4
5
120
85
90
[39]
90
[40]
6
7
150
75
95
[41]
90
[42]
[30]
8
9
90
50
90
95
aReaction conditions: ArB (OH)2 (0.5 mmol), NaN3 (1 mmol), CuI/II@Cys-MGO nanocomposite (0.005 g), H2O:EtOH (1:1) (3 ml), 60ꢀC.

RAFIEE AND KHAVARI
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have found that immobilized copper ions on the surface
of cysteine functionalized magnetic graphene oxide act as
an efficient nanocatalyst in A3-coupling reactions for
propargylamines synthesis.[36]
To study the scope of the CuI/II@Cys-MGO-catalyzed
azidonation reaction, the coupling reaction of various
aryl boronic acids with sodium azide was tested under
optimized reaction conditions. The results are listed in
Table 2. Aryl boronic acids with both electron-
withdrawing and electron-donating substituents afforded
the corresponding aryl azides in good yields.
In
the
preparation
of
CuI/II@Cys-MGO
nanocomposite, magnetic graphene oxide was obtained
via chemical oxidation of the graphite powder, exfoliation
under ultrasonic waves, and magnetization in the pres-
ence of ion salts. The magnetic graphene oxide was modi-
fied with cysteine and used as an efficient support for the
immobilization of copper ions. The prepared
nanocomposite was characterized using FT-IR, Transmis-
sion electron microscope (TEM), energy-dispersive X-ray
(EDX), X-ray powder detection (XRD), vibrating sample
magnetometer (VSM), X-ray photoelectron spectroscopy
(XPS), and quantitative inductively coupled plasma-
optical emission spectroscopy (ICP-OES) analysis. The
oxidation state of copper ions was confirmed by XPS
(Figure 1). XPS analysis of Cu 2P proved that copper ions
are present in two oxidation states. The bands at binding
energies of 934.6, 938.5–944.7 (shake-up’ satellite peaks),
and 955.1 eV are related to CuII 2p3/2 and CuII 2p1/2 and
the peaks at 932.8 and 952.5 eV were assigned to CuI
2p3/2 and CuI 2p1/2, respectively. In the nanocatalyst pro-
duction process, some CuII ions are reduced to CuI due to
the partial oxidation of cysteine to cystine.
The peaks at binding energies of 399.2 and 400.8 eV
in the N 1 s XPS spectrum are assigned to N–C and N–
C=O bonds. In the C 1 s core-level spectrum, a peak for
the nonoxygenated ring C=C is seen at 284.1, for C in C–
OH bonds at 285.3, and for the carbonyl group (C=O) at
287.4 eV. The disappearance of the HO–C=O peak at
~289 in the C 1 s spectrum and the appearance of N–C
and N–C=O peaks in the N 1 s spectrum confirmed
the successful covalent functionalization of cysteine
onto graphene oxide surface through amide bond
formation.
The reusability of CuI/II@Cys-MGO nanocatalyst was
examined in the azidonation reaction of 2-methoxy phe-
nyl boronic acid under the optimized reaction conditions.
The catalyst was separated magnetically after the comple-
tion of the first cycle, washed with ethanol and water,
and dried for use in the next run. A new reaction was car-
ried out with fresh reactants and solvent using recycled
catalyst under the same conditions. As shown in
Figure 2, this catalytic system retained its activity quite
well up to eight times without an obvious reduction in
yield.
A hot filtration test was done to investigate the pres-
ence of the homogeneous copper species in the reaction
mixture due to the leaching process during the coupling
reaction. In a typical reaction, a mixture of 0.005 g of the
catalyst in 2 ml of solvent (EtOH:H2O) was prepared and
stirred at 60ꢀC for 20 min, and then the nanocatalyst was
magnetically removed from the hot reaction mixture and
2-methoxy phenyl boronic acid and sodium azide were
added to the solution and stirred for 20 min. The filtrate
showed no catalytic activity in the azidonation reaction
under the optimized conditions.
After the effective azidonation reaction of aryl
boronic acids using CuI/II@Cys-MGO nanocatalyst, we
next investigated the efficiency of this catalytic system in
the one-pot synthesis of 1,4-diaryl-1,2,3-triazoles via the
coupling reaction of aryl boronic acids with NaN3 and
then phenylacetylene addition without the isolation of
aryl azides (Table 3). The one-pot three coupling reaction
of aryl boronic acids, NaN3, and phenylacetylene was
performed and good results were obtained. However, the
We have now extended CuI/II@Cys-MGO efficiency
in the preparation of aryl azides of aryl boronic acids and
also the synthesis of 1,4-diaryl-1,2,3-triazoles through
one-pot azidonation of arylboronic acids followed by
click cyclization with phenyl acetylene (Scheme 1).
Initially, we investigated the coupling reaction of
2-methoxy-phenyl boronic acid with sodium azide as a
model reaction to explore the optimized reaction condi-
tions. To do this, various parameters such as solvent,
temperature, bioligand type in the composite structure
(cysteine, N-amidinoglycine, histidine, and tyrosine), and
the amount of catalyst were changed and their effects on
conversions and reaction times were studied (Table 1).
The best results were obtained using H2O/EtOH (1:1) as
the solvent at 60ꢀC with 0.005 g of CuI/II@Cys-MGO
nanocatalyst (Table 1, entry 6).
FIGURE 2 Recyclability of CuI/II@Cys-MGO catalyst in the
azidonation reaction

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RAFIEE AND KHAVARI
TABLE 3
One-pot synthesis of 1,4-diaryl-1,2,3-triazoles by CuI/II@Cys-MGO nanocatalysta
Entry
ArB (OH)2
Product
Time (min)
Conversion (%)
Ref.
[30]
1
110
90
[43]
2
3
300
120
85
95
[44]
[44]
4
5
210
240
90
90
[45]
[43]
6
180
90
[46]
7
8
180
110
85
95
[30]
aReaction conditions: ArB (OH)2 (0.5 mmol), NaN3 (1 mmol), phenylacetylene (0.54 mmol),
CuI/II@Cys-MGO nanocatalyst (0.005 g), H2O:EtOH (1:1) (3 ml), 60ꢀC.

RAFIEE AND KHAVARI
7 of 8
cycloaddition is shown in Scheme 2 based on literature
data.[11,47,48] The CuI coordination to phenylacetylene led
to complex 1 formation and then a copper-acetylide inter-
mediate 2 was formed due to the reaction with a second
Cu(I) catalyst. An intermolecular cyclization between
2 and an aryl azide 3 that was obtained via CuII catalyzed
coupling reaction of ayl boronic acid with NaN3 led to
metallacycle 4. The copper triazolide 5 was resulted
through the reductive elimination of metallacycle 4. In
the final step, the 1,4-diaryl-1,2,3-triazole product 6 was
formed and the Cu(I) catalyst was regenerated.
The
catalytic
activity
of
CuI/II@Cys-MGO
nanocatalyst was compared with other catalysts in the
azidonation of 2-methoxy-phenyl boronic acid (Table 4)
and also the azide alkyne cycloaddition of 2-methoxy-
phenyl azide with phenylacetylene (Table 5). The results
show that this catalytic system was acted in shorter reac-
tion times using of lower catalyst loading and with better
yields in comparison with other catalysts.
SCHEME 2 Proposed mechanism of azidonation and the
coupling reaction with phenylacetylene
yield of 1,4-diaryl-1,2,3-triazoles product was better with
the first method.
The coupling reaction of aryl boronic acid with NaN3
required a CuII catalytic system while the reaction of the
corresponding aryl azides with phenylacetylene was cata-
lyzed with CuI catalysts.[32] The nanocatalyst including
both CuI and CuII catalytic species efficiently catalyzed
the one-pot synthesis of 1,4-diaryl-1,2,3-triazoles. The
proposed mechanism for the CuI-catalyzed azide–alkyne
4 | CONCLUSION
We reported an efficient catalytic system containing CuI
and CuII catalytic species that were immobilized on the
magnetic cysteine functionalized graphene oxide and
used for the preparation of aryl azides from the
TABLE 4
Comparison results of CuI/II@Cys-MGO activity with other catalysts in the preparation of aryl azides of aryl boronic acids
Entry
Catalyst (mol%)
Reaction conditions
DMF, 100 ꢀC
Time (hr)
Conversion (%)
Ref.
[49]
1
2
3
4
Cu (TMHD)2 (0.2 mmol)
CuFe2O4 (10 mol %)
CuSO4 (10 mol%)
4
91
85
90
95
[27]
[30]
H2O, r.t.
7
MeOH, r.t. air
5
CuI/II@Cys-MGO (0.5 mol %)
H2O:EtOH (1:1), 60 ꢀC
20 min
Current work
Note. r.t., room temperature.
TABLE 5
Comparison results of CuI/II@Cys-MGO activity with other catalysts in the coupling reaction of aryl azides with
phenylacetylene
Entry Reagent catalyst (mol%)
Reaction conditions Time (h) Conversion (%) Ref.
[30]
1
2-OMe-C6H4-B, (OH)2 + NaN3 + Ph–CꢁC–H, CuSO4
H2O:MeOH, r.t., air
12
92
(10 mol%)
[27]
2
2-OMe-C6H4-B, (OH)2 + NaN3 + Ph–CꢁC–H,
H2O, r.t.
12
86
CuFe2O4 (10 mol%)
[50]
[47]
3
4
2-OMe-C6H4-N3 + Ph–CꢁC–H, Zn/C (10 mol%)
DMF, 50ꢀC
H2O, r.t.
15
10
71
92
2-OMe-C6H4-N3 + Ph–CꢁC–H CuSO4.5H2O (1 mol%),
1-(4-methoxyphenyl)-3-phenylthiourea (1 mol%)
5
2-OMe-C6H4-B (OH)2 + NaN3 + Ph–CꢁC–H,
H2O:EtOH (1:1),
60ꢀC
110 min
90
This work
CuI/II@Cys-MGO (0.5 mol%)

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RAFIEE AND KHAVARI
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ORCID
Fatemeh Rafiee https://orcid.org/0000-0002-7987-600X
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How to cite this article: Rafiee F, Khavari P.
Preparation of aryl azides of aryl boronic acids and
one-pot synthesis of 1,4-diaryl-1,2,3-triazoles by a
magnetic cysteine functionalized GO–CuI/II
nanocomposite. Appl Organomet Chem. 2020;
e5789. https://doi.org/10.1002/aoc.5789
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