Application of Cu(Hdmg)2 as a simple and cost-effective catalyst for the convenient one-pot reductive acetylation of aromatic nitro compounds

Article abstract of DOI:10.1002/jccs.201800325

In this article, we have developed a novel and simple one-pot reductive acetylation of aromatic nitro compounds with sodium borohydride (NaBH₄) in ethyl acetate (EtOAc) under reflux conditions in the presence of the bis(dimethylglyoximato)copper(II) complex [Cu(Hdmg)₂] as an efficient and cost-effective copper-containing catalyst. Notably, using the above-mentioned one-pot reaction, the corresponding acetamide derivatives were obtained in high to excellent yields.

Full text of DOI:10.1002/jccs.201800325

Received: 24 August 2018
Revised and accepted: 19 January 2019
DOI: 10.1002/jccs.201800325
A R T I C L E
Application of Cu(Hdmg) as a simple and cost-effective catalyst
2
for the convenient one-pot reductive acetylation of aromatic nitro
compounds
Behzad Zeynizadeh | Hossein Mousavi | Saviz Zarrin
Department of Organic Chemistry, Faculty of
In this article, we have developed a novel and simple one-pot reductive acetylation
Chemistry, Urmia University, Urmia, Iran
of aromatic nitro compounds with sodium borohydride (NaBH ) in ethyl acetate
Correspondence
4
Hossein Mousavi, Department of Organic
Chemistry, Faculty of Chemistry, Urmia
University, Urmia, Iran.
(EtOAc) under reflux conditions in the presence of the bis(dimethylglyoximato)
copper(II) complex [Cu(Hdmg) ] as an efficient and cost-effective copper-
2
containing catalyst. Notably, using the above-mentioned one-pot reaction, the cor-
responding acetamide derivatives were obtained in high to excellent yields.
Email: 1hossein.mousavi@gmail.com
Funding information
Research Council of Urmia University
KEYWORDS
aromatic nitro compound, copper complex, Cu(Hdmg) , N-arylacetamide,
2
one-pot, reductive acetylation
1
| INTRODUCTION
In recent decades, copper and copper-containing complex
catalytically systems have been used in various types of
[
6]
Amides are one of the most important functional groups in
organic chemistry because of their presence in numerous
valuable compounds such as proteins, peptides, agrochemi-
cals, insecticides, biologically active molecules, advanced
materials, and so on. On the other hand, they are common
subunits in various commercially available marketed drugs
and also natural products (Figure 1). They are also used as
ligands in stabilizing various metal centers. Recently,
some of the amide-containing tripodal compounds have been
reported as chemosensors.
One-pot reactions are very important tools for the syn-
thesis of valuable organic frameworks because of their short
reaction times, least waste production, low costs, very sim-
ple approach, high atom economy, and environmental
friendless. Because of these reasons and the other unique
features of these reactions, organic and medicinal chemists
have widely applied one-pot multicomponent reactions
organic transformations. Notably, copper is an inexpensive
earth-abundant transition metal that can promote a variety of
reactions because of a wide range of accessible oxidation
0
I
II
III
states including Cu , Cu , Cu , and also Cu , which enable
reactivity via both one-electron and two-electron path-
[1]
[7]
ways. Because of their interesting features and properties,
selection of copper or copper-based complexes as catalysts
is an excellent option.
According to the above-mentioned issues, we wish to
report a new and convenient one-pot strategy for the reduc-
tive acetylation of aromatic nitro compounds catalyzed by
Cu(Hdmg)2 as a simple and cost-effective copper-based
[2]
[3]
complex with NaBH in ethyl acetate (EtOAc) under reflux
4
conditions (Scheme 1).
[
4]
2 | RESULTS AND DISCUSSION
(MCRs) to synthesize various bioactive compounds.
Transition metal-based catalysts play a pivotal role in the
organic synthetic and industrial chemical processes.
One of the straightforward, valuable, and economic methods
for the preparation of amides (especially acetamide
[
5]
©
2019 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J Chin Chem Soc. 2019;1–6.
http://www.jccs.wiley-vch.de
1

2
ZEYNIZADEH ET AL.
[15]
[
14]
CH OH/r.t.),
([Na SO –AcOH]/boiling Ac O),
([(Nano
3
2
3
2
ꢀ
[16]
Pd/ZnO)–N H .H O–Ac O]/H O:EtOH/90 C), and ([Fe O4
2
4
2
2
2
3
ꢀ
[17]
@
Cu(OH) -NaBH -Ac O]/H O/60 C) are available for this
x 4 2 2
mentioned one-pot reaction. In this regard, introducing new,
simple, and practical catalytic protocols for the selective prepa-
ration of acetamide derivatives via one-pot reductive acetyla-
tion of nitroarenes is very important in the chemical industry,
in particular, for organic synthesis.
First of all, we prepared Cu(Hdmg) using a simple oper-
2
[
18]
ation reported in the literature.
Briefly, dimethylglyoxime
(
H dmg) and copper(II) acetate monohydrate were added to
2
absolute ethanol with a molar ratio of 2:1 in sequence, which
was stirred at room temperature for 30 min to obtain brown
precipitates Cu(Hdmg) (Scheme 2). The structure of the
2
complex was characterized using FT-IR spectroscopy and
the melting point. A strong adsorption peak belonging to
−
1
Cu–N appeared at 486 cm . Also, the strong band of the
ligand at 1540 cm− confirmed the formation of a C=NÁÁÁCu
bond. The mentioned complex has a flat square structure, so
it has free and open space from above and below. This
empty space can provide a catalytically active surface to
accelerate the reaction.
1
After preparation of Cu(Hdmg) , we were interested in
2
investigating the catalytic activity of this copper-based com-
plex in the one-pot reductive acetylation of aromatic nitro
compounds using sodium borohydride (NaBH ) as a mild
4
reducing agent with EtOAc as a solvent that plays the role of
an acetylating agent. Notably, the arrangement of adding
materials into the reaction environment strongly affected the
reaction time. According to this topic, the best model for
doing the reductive acetylation reaction is as follows. First,
an aromatic nitro compound, EtOAc, and NaBH4 were
FIGURE 1 Example of amide-containing drugs and natural products
SCHEME 1 One-pot reductive acetylation of aromatic nitro compounds
mixed together and after about 10–20 min Cu(Hdmg) was
2
added to the reaction medium. However, we envisioned that
if in the beginning, an aromatic nitro compound, EtOAc,
and Cu(Hdmg)2 were mixed together and after about
1
0–20 min NaBH was added to the reaction environment,
4
catalyzed by Cu(Hdmg)
2
the reaction time became very long. As shown in Table 1,
the mentioned one-pot reaction tolerated a variety of aro-
matic nitro compounds bearing both electron-donating and
electron-withdrawing groups in the ortho, meta, and para
positions. It should be noted that the presented catalytic
reductive acetylation protocol showed chemoselectivity (just
in the acetylation step) in the presence of other acetylable
functional group (viz. OH). In the reactions where the aro-
matic molecule has two different functional groups such as
derivatives) is one-pot reductive acetylation of aromatic nitro
compounds. Literature survey showed that only a few reports
[8]
such as ([Zn powder-acidic Al O –Ac O]/CH Cl /r.t.),
2
3
2
2
2
ꢀ
[9]
[10]
(
(
[Fe–AcOH]/100–110 C), ([In-Ac O–AcOH]/CH OH/r.t.),
2
3
[11]
[SmI -EtOAc]/THF/under N (g)/r.t.),
([KSCOCH ]/DMF/130 C),
Triton-X 405)]/solvent-free/130 C),
([Sm-Ac O–AcOH]/
([KSCOCH3-
([(Pt/ZrO )–Ac O]/
2
2
2
[12]
ꢀ
[13]
CH OH/r.t.),
(
3
3
ꢀ
[13]
2
2
2
SCHEME 2 Preparation of the Cu(Hdmg) complex

ZEYNIZADEH ET AL.
3
TABLE 1 One-pot preparation of N-arylacetamides
a
Entry
Substrate
Product
Molar ratio
Time (min)
Yield (%)
1
1:3:0.1
170
93
2
3
4
1:3:0.15
1:3:0.15
1:3:0.15
170
140
155
93
91
96
5
1:3:0.1
170
91
6
7
1:3:0.2
180
145
92
92
1:3.0.15
8
9
1:3:0.2
170
95
1:3:0.1
1:3:0.2
170
240
94
96
1
0
a
4 2
Substrate:NaBH :Cu(Hdmg) .

4
ZEYNIZADEH ET AL.
TABLE 2 Comparison of the current one-pot reductive acetylation protocol with other previously reported methods
Time
Yield
(%)
Entry
Reductive acetylation system
[Zn powder-acidic Al –Ac O]/CH
(min)
720
840
120
30
Ref.
[8]
1
2
3
4
5
6
7
8
9
2
O
3
2
2
Cl
2
/r.t.
50
81
92
89
86
83
78
93
90
90
94
97
ꢀ
[Fe-AcOH]/100–110 C
[In-Ac O–AcOH]/CH OH/r.t.
[SmI -ethyl acetate]/THF/under N
[Sm-Ac O-AcOH]/CH OH/r.t.
[9]
2
3
[10]
[11]
[12]
[13]
[13]
[14]
[15]
[16]
[17]
This work
2
2
(g)/r.t.
2
3
270
120
120
210
960
195
6
ꢀ
[KSCOCH
3
]/DMF/130 C
-(Triton-X 405)]/solvent-free/130 C
O]/CH OH/r.t.
–AcOH]/boiling Ac
[(Nano Pd/ZnO)–N .H O–Ac
[Fe @Cu(OH) –NaBH –Ac O]/H
[Cu(Hdmg) –NaBH –EtOAc]/Reflux
ꢀ
[KSCOCH
3
[(Pt/ZrO
[Na SO
2
)–Ac
2
3
2
3
2
O
ꢀ
10
11
12
2
H
4
2
2
O]/H
2
O:EtOH/90 C
ꢀ
3
O
4
x
4
2
2
O/60 C
2
4
170
nitro and hydroxyl (Table 1, entries 2–4), only the nitro
functional group was converted into amide and hydroxyl
functional group remains unchanged (not became an ester).
Furthermore, the aldehyde functional groups that existed in
the molecular structure of nitroarenes just reduced and
turned into the corresponding alcohols under reaction condi-
tions (Table 1, entries 6–9). The efficiency of the current
protocol for the reductive acetylation of the nitroarenes to
the corresponding acetamides was compared with previous
literature. The results of this comparison are listed in
Table 2. As shown in Table 2, the current strategy is better
than other methods in terms of yield. Also, this method is
relatively better in terms of reaction time.
CDCl (or DMSO-d ) as a solvent relative to tetramethylsi-
3 6
lane as the internal standard.
3
.2 | General procedure for the one-pot reductive
acetylation of aromatic nitro compounds
As a representative example, in a round-bottom flask
(
10 mL) equipped with a magnetic stirrer, a mixture of nitro-
benzene (1 mmol) in EtOAc (2 mL) was prepared. NaBH4
3 mmol) was then added and the mixture was stirred for
0 min. Next, Cu(Hdmg)2 (0.1 mmol) was added to the
(
2
reaction medium and the resulting mixture was stirred vigor-
ously for an appropriate time under reflux conditions. After
completion of the reaction (checked by thin-layer chromatog-
raphy), the reaction mixture was cooled to room temperature,
and then 5 mL of distilled water was added, and the reaction
mixture was continued to stir for 5 min. The mixture was
extracted with CH Cl (3 × 5 mL) and then dried over anhy-
It should be noted that the accurate mechanism of
Cu(Hdmg) -catalyzed one-pot reductive acetylation of the
2
aromatic nitro compounds is unclear. Despite this issue, a
plausible mechanism for the mentioned reaction is shown in
Scheme 3.
2
2
drous sodium sulfate. Evaporation of the solvent followed by
further purification using a short-column chromatography
over silica gel afforded the pure acetanilide in 93% yield.
3
3
| EXPERIMENTAL
4
| CONCLUSIONS
.1 | Reagents and apparatus
Chemicals were purchased from the Merck, Fluka, and
Sigma-Aldrich chemical companies. Melting points were
determined on an Electrothermal 9200 apparatus. Infrared
spectra were recorded on a Nexus 670 Thermo Nicolet Fou-
rier Transform Infrared Spectrometer and measured using
In summary, we have developed a new, general, and simple
strategy for the efficient one-pot reductive acetylation of aro-
matic nitro compounds by NaBH in EtOAc under reflux
4
conditions using Cu(Hdmg)2 as a cost-effective catalyst.
With the use of the mentioned strategy, a series of aromatic
amides (in some cases along with another acetylable func-
tional group namely the hydroxyl functional group) were
obtained in high to excellent yields.
1
13
KBr discs. H NMR and C NMR spectra were recorded on
a Bruker Avance 300 MHz spectrometer at 300 and
75 MHz, respectively. Chemical shifts were measured in

ZEYNIZADEH ET AL.
5
SCHEME 3 Plausible mechanism for the one-pot reductive acetylation of aromatic nitro compounds catalyzed by Cu(Hdmg)
2
ACKNOWLEDGMENT
2018, 3, 2599. c) K. V. Sashidhara, G. R. Palnati, R. P. Dodda, R. Sonkar,
A. K. Khanna, G. Bhatia, Eur. J. Med. Chem. 2012, 57, 302. d)
R. Sirgamalla, A. Kommakula, S. Banoth, R. Dharavath, K. Adem,
P. Madhu, S. Boda, ChemistrySelect 2018, 3, 1062. e) Y. Jaiswal,
Y. Kumar, A. Kumar, J. Org. Chem. 2018, 83, 1223. f) T. F. Molinski,
Org. Biomol. Chem. 2018, 16, 21. g) D. C. Simkó, P. Elekes, V. Pázmándi,
Z. Novák, Org. Lett. 2018, 20, 676. h) F. S. Tareq, H. J. Shin, J. Nat. Prod.
Financial support from the Research Council of Urmia Uni-
versity is gratefully acknowledged.
CONFLICT OF INTEREST
2017, 80, 2889. i) J. W. Bluent, A. R. Carrol, B. R. Copp, R. A. Davis,
R. A. Keyzers, M. R. Prinsep, Nat. Prod. Rep. 2018, 35, 8. j)
P. M. E. Hawkins, A. M. Giltrap, G. Nagalingam, W. J. Britton,
R. J. Payne, Org. Lett. 2018, 20, 1019. k) R. Ningegowda, S. Bhaskaran,
A. M. Sajith, C. Aswathanaryanappa, M. S. A. Padusha, N. S. Shivananju,
B. S. Priya, Aust. J. Chem. 2017, 70, 44. l) M. R. Gudisela, P. Bommu,
S. Navuluri, N. Mulakayala, ChemistrySelect 2018, 3, 7152. m) J. Lee,
M. M. Joullié, Chem. Sci. 2018, 9, 2432. n) S. Adachi, N. Kumagai,
M. Shibasaki, Tetrahedron Lett. 2018, 59, 1147. o) M. Keyhani, A. Shiri,
H. Eshghi, A. Khojastehnezhad, Appl. Organometal. Chem. 2018, 32,
e4344. p) F. H. Al-Awadhi, B. K. Law, V. J. Paul, H. Luesch, J. Nat. Prod.
The authors declare no conflict of interest.
ORCID
Behzad Zeynizadeh https://orcid.org/0000-0003-0485-
5455
Hossein Mousavi https://orcid.org/0000-0003-4292-3762
2017, 80, 2969. q) S. Son, Y.-S. Hong, M. Jang, K. T. Heo, B. Lee, J.-
REFERENCES
P. Jang, J.-W. Kim, I.-J. Ryoo, W.-G. Kim, S.-K. Ko, B. Y. Kim, J.-
H. Jang, J. S. Ahn, J. Nat. Prod. 2017, 80, 3025. r) C. Urda, R. Fernández,
[1] a) L. Deng, B. Huang, Y. Liu, Org. Biomol. Chem. 2018, 16, 1552. b)
Z. Wang, X. Bao, M. Xu, Z. Deng, Y. Han, N. Wang, ChemistrySelect

6
ZEYNIZADEH ET AL.
J. Rodríguez, M. Pérez, C. Jiménez, C. Cuevas, J. Nat. Prod. 2017, 80,
045.
H. Mousavi, Res. Chem. Intermed. 2018, 44, 7331. o) S. A. Fazeli-Attar,
B. B. F. Mirjalili, Res. Chem. Intermed. 2018, 44, 6419.
3
[
2] a) N. Kumagai, M. Shibasaki, Angew. Chem. Int. Ed. 2013, 52, 223. b)
H. Cheng, B. Zhao, Y. Yao, C. Lu, Green Chem. 2015, 17, 1675. c)
J. C.-H. Yim, J. A. Bexrud, R. O. Ayinal, D. C. Leitch, L. L. Schafer,
J. Org. Chem. 2014, 79, 2015.
3] J. Sun, X. Xu, G. Yu, W. Li, J. Shi, Tetrahedron 2018, 74, 987.
4] a) K. A. Grice, R. Patil, A. Ghosh, J. D. Paner, M. A. Guerrero,
E. J. M. Camacho, P. S. Cao, A. H. Niyazi, S. Zainab, R. D. Sommer,
G. Waris, S. Patil, New J. Chem. 2018, 42, 1151. b)
A. Mohammadinezhad, B. Akhlaghinia, Aust. J. Chem. 2018, 71, 32. c)
S. Kumari, M. Rajeswari, J. M. Khurana, Aust. J. Chem. 2016, 43, 1735. d)
M. Rimaz, B. Khalili, G. Khatyal, H. Mousavi, F. Aali, Aust. J. Chem.
[6] a) J. E. Hein, V. V. Fokin, Chem. Soc. Rev. 2010, 39, 1302. b) F. Guo,
D. Chang, G. Lai, T. Zhu, S. Xiong, S. Wang, Chem. Eur. J. 2011, 17, 11130.
c) A. Gogoi, G. Sarmah, A. Dewan, U. Bora, Tetrahedron Lett. 2014, 55, 31. d)
P. Gogoi, M. Kalita, T. Bhattacharjee, P. Barman, Tetrahedron Lett. 2014, 55,
1028. e) H. Inomata, A. Toh, T. Mitsui, S.-i. Fukuzawa, Tetrahedron Lett.
2013, 54, 4729. f) B. Ni, J. He, Tetrahedron Lett. 2013, 54, 462. g) X. Ge,
F. Sun, X. Liu, X. Chen, C. Qian, S. Zhou, New J. Chem. 2017, 41, 13175. h)
P. C. Perumgani, S. Keesara, S. Parvathaneni, M. R. Mandapati, New J. Chem.
2016, 40, 5113. i) A. Jehdarmarn, S. Pornsuwan, P. Chumsaeng, K. Phomphrai,
P. Sangtrirutnugul, New J. Chem. 2018, 42, 654. j) Z. Xu, X. Yu, X. Sang,
D. Wang, Green Chem. 2018, 20, 2571. k) J.-R. Cammarata, R. Rivera,
F. Fuentes, Y. Otero, E. Ocando-Mavárez, A. Arce, J. M. Garcia, Tetrahedron
Lett. 2017, 58, 4078. l) L. Harmand, P. Drabina, V. Pejchal, L. Husáková,
M. Sedlák, Tetrahedron Lett. 2015, 56, 6240. m) J. Safaei-Ghomi, H. Shahbazi-
Alavi, S. H. Nazemzadeh, J. Chin. Chem. Soc. 2017, 64, 1213. n) S. Kazemi,
A. Mobinkhaledi, M. Zendehdel, J. Chin. Chem. Soc. 2017, 64, 764.
[7] a) M. B. Gawande, A. Goswami, F.-X. Felpin, T. Asefa, X. Huang,
R. Silva, X. Zou, R. Zboril, R. S. Varma, Chem. Rev. 2016, 116, 3722. b)
S. E. Allen, R. R. Walvoord, R. Padilla-Salinas, M. C. Kozlowski, Chem.
Rev. 2013, 113, 6234. c) A. P. Shah, A. S. Sharma, S. Jain, N. G. Shimpi,
New J. Chem. 2018, 42, 8724.
[
[
2017, 70, 1274. e) J. Sindhu, H. Singh, J. M. Khurana, K. R. Aneja, Aust.
J. Chem. 2013, 66, 717. (f) H. Singh, J. Sindhu, J. M. Khurana, C. Sharma,
K. R. Aneja, Aust. J. Chem. 2013, 66, 1088. g) S. J. Jadhav, R. B. Patil,
D. R. Kumbhar, A. A. Patravale, D. R. Chandam, M. B. Deshmukh,
J. Heterocyclic Chem. 2017, 54, 2434. h) M. Beerappa, K. Shivashankar,
J. Heterocyclic Chem. 2017, 54, 2197. i) M. Rimaz, J. Khalafy,
H. Mousavi, S. Bohlooli, B. Khalili, J. Heterocyclic Chem. 2017, 54, 3174.
j) M. Rimaz, H. Mousavi, Turk. J. Chem. 2013, 37, 252. k) M. Rimaz,
Z. Jalalian, H. Mousavi, R. H. Prager, Tetrahedron Lett. 2016, 57, 105. l)
M. Rimaz, J. Khalafy, H. Mousavi, Res. Chem. Intermed. 2016, 42, 8185.
m) M. N. Elison, F. V. Ryzhkov, A. N. Vershchagin, A. S. Goloveshkin,
I. S. Bushmarinov, M. P. Egorov, Res. Chem. Intermed. 2018, 44, 3199. n)
H. Kiyani, M. Bamdad, Res. Chem. Intermed. 2018, 44, 2761. o)
M. Rimaz, H. Mousavi, B. Khalili, F. Aali, J. Chin. Chem. Soc. 2018, 65,
[8] R. N. Baruah, Indian J. Chem. 2000, 39B, 300.
[9] K. Y. Lee, J. M. Kim, J. N. Kim, Bull. Korean Chem. Soc. 2002, 23, 1355.
[10] B. H. Kim, R. Han, F. Piao, Y. M. Jun, W. Baik, B. M. Lee, Tetrahedron
Lett. 2003, 44, 77.
1
389. p) M. Rimaz, H. Mousavi, L. Nikpey, B. Khalili, Res. Chem.
[11] X. Wang, H. Guo, G. Xie, Y. Zhang, Synth. Commun. 2004, 34, 3001.
[12] Y.-S. Jia, Q. Li, X.-H. Wang, H. L. Wang, X.-T. Liu, J. Shang. Univ. 2006,
10, 277.
[13] A. Bhattacharya, V. C. Purohit, V. Suarez, R. Tichkule, G. Parmer,
F. Rinaldi, Tetrahedron Lett. 2006, 47, 1861.
[14] M. L. Kantam, R. S. Reddy, K. Srinivas, R. Chakravarti, B. Sreedhar,
F. Figueeras, C. V. Reddy, J. Mol. Catal. A: Chem. 2012, 355, 96.
[15] M. Ghaffarzadeh, P. Akhavan, Chem. Lett. 2014, 43, 1417.
[16] M. Hosseini-Sarvari, Z. Razmi, Appl. Surf. Sci. 2015, 324, 265.
[17] Z. Shokri, B. Zeynizadeh, S. A. Hosseini, J. Colloid Interface Sci. 2017,
485, 99.
Intermed. 2017, 43, 3925. q) M. Rimaz, H. Mousavi, M. Behnam,
L. Sarvari, B. Khalili, Curr. Chem. Lett. 2017, 6, 55. r) G. Khanna,
P. Saluja, J. M. Khurana, Aust. J. Chem. 2017, 70, 1285. s) M. Gholami
Dehbalaei, N. Foroughifar, A. Khajeh-Amiri, H. Pasdar, J. Chin. Chem.
Soc. 2018, 65, 1356. t) N. Iravani, M. Keshavarz, F. Hosseini, J. Chin.
Chem. Soc. 2018, 65, 1098. u) R. Mohebat, P. Dehgan, A. Yazdani-Elah-
Abadi, J. Chin. Chem. Soc. 2018, 65, 1259. v) A. Rezvanian, V. Zadsirjan,
P. Saedi, M. M. Heravi, J. Heterocyclic Chem. 2018, 55, 2772. w)
T. Zhang, J. Zhou, Y. Chen, Y. Li, Res. Chem. Intermed. 2018, 44, 5329.
x) V. N. Mahire, G. P. Patil, A. B. Deore, P. G. Chavan, H. D. Jirimali,
P. P. Mahulikar, Res. Chem. Intermed. 2018, 44, 5801. y) S. Sadjadi,
M. M. Heravi, V. Zadsirjan, V. Farzaneh, Res. Chem. Intermed. 2018, 44,
[18] X.-L. Li, X.-Y. Zhu, T.-L. Duan, Y.-T. Qian, Solid State Commun. 2006,
138, 526.
6765. z) M. Safarzaei, M. T. Maghsoodlou, E. Mollashahi, N. Hazeri,
M. Lashkari, Res. Chem. Intermed. 2018, 44, 7449.
5] a) D. Perrotta, M.-M. Wang, J. Waser, Angew. Chem. Int. Ed. 2018, 130,
SUPPORTING INFORMATION
[
Additional supporting information may be found online in
the Supporting Information section at the end of the article.
5214. b) A. U. Augustin, M. Busse, P. G. Jones, D. B. Werz, Org. Lett. 2018,
20, 820. c) S. G. Lee, S. Sin, S. Kim, S.-G. Kim, Tetrahedron Lett. 2018, 59,
1480. d) K. Nikoofar, Z. Khademi, Res. Chem. Intermed. 2016, 42, 3929. e)
M. Rimaz, H. Mousavi, P. Keshavarz, B. Khalili, Curr. Chem. Lett. 2015, 4,
159. f) M. Rimaz, H. Mousavi, M. Behnam, B. Khalili, Curr. Chem. Lett.
2016, 5, 145. g) M. Liu, S. Qiu, Y. Ye, G. Yin, Tetrahedron Lett. 2016, 57,
5856. h) A. P. A. Gouveia, J. G. Taylor, ChemistrySelect 2018, 3, 3965. i)
How to cite this article: Zeynizadeh B, Mousavi H,
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2
W. H. dos Santos, I. A. Leonarczyk, M. A. B. Ferreira, L. C. da Silva-Filho,
Synthesis 2402, 2017, 49. j) E. Li, C. Li, J. Wang, J. Wang, L. Dong, X. Guo,
C. Song, J. Chang, Tetrahedron 2014, 70, 874. k) A. Ziyaei Halimehjan,
N. Keshavarzi, J. Heterocyclic Chem. 2018, 55, 522. l) D. Wang, D. Astruc,
Chem. Soc. Rev. 2017, 46, 816. m) H. Mousavi, B. Zeynizadeh, R. Younesi,
M. Esmati, Aust. J. Chem. 2018, 71, 595. n) B. Zeynizadeh, R. Younesi,
cost-effective catalyst for the convenient one-pot
reductive acetylation of aromatic nitro compounds.
J Chin Chem Soc. 2019;1–6. https://doi.org/10.1002/
jccs.201800325