Synthesis and characterization of magnetic copper ferrite nanoparticles and their catalytic performance in one-pot odorless carbon-sulfur bond formation reactions

Article abstract of DOI:10.1016/j.molcata.2014.02.006

In this article, we have introduced catalytic application of copper ferrite nanoparticles (CuFe₂O₄) for one-pot odorless production of aryl alkyl thioethers using thiourea and alkyl bromides in wet polyethylene glycol as a green solvent. The catalyst was also successfully applied for one-pot synthesis of symmetrical diaryl trithiocarbonates via the reaction of sodium sulfide, carbon disulfide and aryl iodides under heterogeneous reaction condition. Magnetic copper ferrite nanoparticles were synthesized using iron (III) chloride and copper (II) chloride, and characterized using XRD, FT-IR, AAS, and TEM analysis. The catalyst was recycled using simple magnetic separation and reused for the five consecutive runs in the reaction of iodobenzene, thiourea and benzyl bromide without appreciable loss of activity.

Full text of DOI:10.1016/j.molcata.2014.02.006

Journal of Molecular Catalysis A: Chemical 386 (2014) 20–27
Contents lists available at ScienceDirect
Journal of Molecular Catalysis A: Chemical
journal homepage: www.elsevier.com/locate/molcata
Synthesis and characterization of magnetic copper ferrite
nanoparticles and their catalytic performance in one-pot odorless
carbon-sulfur bond formation reactions
Mohammad Gholinejad∗, Babak Karimi, Fariborz Mansouri
Department of Chemistry, Institute for Advanced Studies in Basic Sciences, Gava Zang, Zanjan 45137-66731, Iran
a r t i c l e i n f o
a b s t r a c t
Article history:
In this article, we have introduced catalytic application of copper ferrite nanoparticles (CuFe2O4) for one-
pot odorless production of aryl alkyl thioethers using thiourea and alkyl bromides in wet polyethylene
glycol as a green solvent. The catalyst was also successfully applied for one-pot synthesis of symmetrical
diaryl trithiocarbonates via the reaction of sodium sulfide, carbon disulfide and aryl iodides under het-
erogeneous reaction condition. Magnetic copper ferrite nanoparticles were synthesized using iron (III)
chloride and copper (II) chloride, and characterized using XRD, FT-IR, AAS, and TEM analysis. The catalyst
was recycled using simple magnetic separation and reused for the five consecutive runs in the reaction
of iodobenzene, thiourea and benzyl bromide without appreciable loss of activity.
Received 7 December 2013
Received in revised form 4 February 2014
Accepted 6 February 2014
Available online 17 February 2014
Keywords:
Carbon-sulfur
CuFe2O4
© 2014 Elsevier B.V. All rights reserved.
Nanoparticles
Odorless
Heterogeneous
1. Introduction
nanoparticles as an efficient catalyst for carbon–carbon bond for-
mation via the Sonogashira–Hagihara reaction under ligand-free
The choice of catalyst support plays an important role in
the overall performance of the catalytic systems. Despite their
handling simplicity, heterogeneous catalysts are typically less
effective than their homogeneous counterparts [1]. Moreover,
many of the heterogeneous catalysts are very difficult to sep-
arate from the reaction mixture by classical methods such as
filtration and centrifugation. Along this line, preparation of mag-
netically separable catalysts based on transition metals such as
palladium [2–5], cobalt [6] and copper [7–9] derivatives have
been well explored in recent years. However, less attention has
been focused on direct catalytic applications of magnetic nanopar-
ticles in organic transformations [10–16]. Ortho-Benzoylation of
phenols [10], synthesis of diselenides and ditellurides by cross
coupling of Se(0) or Te(0) with aryl iodides [11], synthesis of
2,3-dihydro-2-thioxoquinazolin-4(1H)-ones [12], addition of acid
chlorides to alkynes [13], N-monoalkylation of aromatic amines
with benzylic alcohols [14], reduction of olefins [15] and syn-
thesis of ␣-aminonitriles [16] are examples of direct using of
Fe3O4 nanoparticles as a catalyst in literature. Recently, we have
introduced application of paramagnetic iron oxide (Fe3O4)
conditions [17]. Among the several magnetic materials tested,
copper ferrites have attracted wide interest as a catalyst in
recent years due to synergetic catalytic effect between copper
and iron sites [18]. In this regard CuFe2O4 nanoparticles without
any functionalization have been used as a magnetically recov-
erable nano-catalyst in various catalytic organic transformations
[19–31].
The construction of carbon–sulfur bond is one of the most
important chemical reactions, since the resulting products con-
tain important structural motifs of numerous biologically and
pharmaceutically active compounds [32,33]. For example, aryl sul-
fide moieties are vital building blocks in the structure of some
medicines for the treatment of Alzheimer, Parkinson, diabetes,
and as anti HIV and anti-inflammatory [34–40]. The traditional
method for the synthesis of aryl sulfides is the Ullmann-type C
S
cross-coupling reaction between thiols and aryl halides. How-
ever, this reaction typically has performed under harsh reaction
conditions, such as elevated temperatures (>200 ◦C) and required
high boiling-point polar solvents such as quinoline, HMPA or
N,N-dimethylacetamide (DMAC) that usually have toxic nature
[41,42].
In order to reduce the mentioned drawbacks and providing
mild reaction conditions, different transition metal catalysts such
as copper [43–59], palladium [60–69], nickel [70], cobalt [71],
∗
Corresponding author.
E-mail address: gholinejad@iasbs.ac.ir (M. Gholinejad).
http://dx.doi.org/10.1016/j.molcata.2014.02.006
1381-1169/© 2014 Elsevier B.V. All rights reserved.

M. Gholinejad et al. / Journal of Molecular Catalysis A: Chemical 386 (2014) 20–27
21
indium [72,73], iron [74,75] and manganese salts [76] were devel-
oped for the coupling reaction of thiols with aryl compounds. In
addition, some efforts have been made in developing of
carbon–sulfur bond forming in more eco-friendly solvents such
as water [77–79]. Although, significant improvement has been
achieved in this area, the main limitations of current protocols are
still using of volatile and foul smelling thiols with low molecular
weight as the substrate that can leads to the serious safety and
environmental problems.
black precipitate was formed immediately indicating the forma-
tion of copper ferrite nanoparticles. Then, the reaction mixture
was heated to 90 ◦C and stirred for 5 h in this temperature. Sub-
sequently, CuFe2O4 magnetic nanoparticles were separated with
external magnet and washed with deionized water (4× 10 mL) and
EtOH (4× 10 mL) then dried in air oven at 80 ◦C for overnight.
Finally, the obtained nanoparticles were calcinated at 700 ◦C for
5 h.
To overcome these drawbacks, two important protocols for
S bond construction under one-pot odorless reaction condi-
2.2. General procedure for thioarylation reactions
C
tions reported by us. In the first report, one-pot odorless C S bond
formation via Michael addition reaction using thiourea and alkyl
bromides was described [80] This method was also extended for
odorless thioarylation of alkyl bromides with aryl halides in the
presence of copper (I) iodide in wet PEG 200 [81].
Our second protocol for one-pot carbon–sulfur bond formation,
has described copper (I) iodide-catalyzed synthesis of symmetri-
cal diaryl trithiocarbonates using the reaction of sodium sulfide,
carbon disulfide and aryl halides [82].
Encouraging by our first new concept, several research groups
and us have started to apply one-pot odorless thioetherification
reaction using different copper or palladium catalysts and dif-
ferent sulfur surrogates such as thiourea [83–85], thioacetamide
[86], potassium thiocyanate [87–89], thioacetate [90], potassium
ethyl xanthogenate [91], sodium hydrosulfide [92], potassium 5-
methyl-1,3,4-oxadiazole-2-thiolate [93], aminothiourea [94] and
elemental sulfur [95,96]. However, in most of these reported meth-
ods, carbon sulfur bond formation reaction was performed under
homogeneous and non-recoverable reaction conditions.
Despite the significant achievements in some of these reports,
homogeneous catalysts suffer being difficult to separate from the
product and problems associated with the recycling of the catalyst.
This issue has paramount importance for pharmaceutically active
materials, because there are typically strict guidelines to limit the
levels of metals impurity in the drug substance. To the best of our
knowledge, there is only one report in the literature on using of cop-
per grafted furfural imine-functionalized mesoporous SBA-15 for
one-pot thioetherification of aryl halides with thiourea and benzyl
bromide in water [53].
In a 5 mL flask, aryl halide (1 mmol), alkyl halide (1.1 mmol),
thiourea (91 mg, 1.2 mmol), CuFe2O4 (12 mg, 5 mol%), K2CO3
(552 mg, 4.0 mmol), H2O (0.3 mL), and PEG (2 mL) were added
and stirred at 80–100 ◦C for the appropriate reaction time. After
completion of reaction, the mixture was cooled to room tem-
perature and washed with 5 mL H2O and 10 mL EtOAc. Then,
after separation and evaporation of organic solvent, the crude
thioethers, were purified by flash column chromatography on
silica gel eluted with the appropriate mixture of (EtOAc/n-
hexane).
2.3. General procedure for the synthesis of diaryl
trithiocarbonates
To the stirring mixture of Na2S (1.1 mmol) in DMF (2 mL),
CS2 (5 mmol) was added at room temperature and mixture was
stirred for 15 min. Then, CuFe2O4 (12 mg, 5 mol%) and aryl iodides
(2 mmol) were added to the reaction mixture and stirred at 100 ◦C
for appropriate reaction time. After completion of reaction, the
reaction mixture was cooled to room temperature and extracted
with EtOAc. Evaporation of the solvent yielded the crude diaryl
trithiocarbonate which was purified by flash column chromatog-
raphy on silica gel (EtOAc/n-hexane).
3. Results and discussion
CuFe2O4 nanoparticles were prepared without using any cap-
ping agent or surfactant via conventional co-precipitation of copper
(II) chloride and iron (III) chloride according to the reported proce-
dure [97]. Thanks to its magnetic nature, the CuFe2O4 nanoparticles
conveniently collected in a side wall of reactor by using a hand-
held magnet during the separation and washing processes. Then,
the catalyst was characterized using various physicochemical tech-
niques including XRD, TEM and FT-IR analysis. Also, the copper and
iron contents were measured by atomic absorption spectroscopy.
Based on the AAS analysis the contents of Cu and Fe in the prepared
CuF2O4 nanoparticles were found to be 26.4 wt% (4.2 mmolCu/g)
and 32.3 wt%, respectively.
Now in this work, we report the synthesis and characterization
of CuFe2O4 nanoparticles as a highly recyclable and heterogeneous
catalyst for the odorless thioetherification of aryl halides using
alkyl halides and thiourea in wet polyethylene glycol as a green
solvent. Also, the catalyst was successfully utilized for the syn-
thesis of symmetrical diaryl trithiocarbonates from the reaction of
sodium sulfide, carbon disulfide and aryl iodides under heteroge-
neous reaction condition. The catalyst can be easily and completely
separated from the final reaction mixture by employing an external
magnetic field.
The structure of the synthesized CuFe2O4 nanoparticles was
confirmed using X-ray diffraction analysis. The XRD pattern of
the as-prepared CuFe2O4 nanoparticles was in good agreement
with the standard of cubic structure of copper ferrite (JCPDS 77-
0010) (Fig. 1). In addition, the strong and sharp reflection peaks in
XRD pattern prove the crystalline nature of the prepared CuF2O4
nanoparticles.
2. Experimental
2.1. General procedure for the preparation of CuFe2O4
nanoparticles
Copper ferrite nanoparticles were prepared via the conventional
co-precipitation method using FeCl3·6H2O and CuCl2·2H2O in an
argon atmosphere. In a typical procedure a solution of FeCl3·6H2O
(2.216 g, 8.2 mmol) and CuCl2·2H2O (699 mg, 4.1 mmol) in 75 ml
deionized water was prepared and stirred at room temperate
under continuous flow of argon atmosphere. In this condition a
basic solution containing 3 g NaOH in 15 mL deionized water was
added drop-wise during 10 min to the above mentioned solu-
tion under vigorous stirring. During the addition of basic solution,
The structure of CuFe2O4 magnetic nanoparticles was further
characterized with FT-IR spectroscopy. The presence of stretch-
ing mode for Fe O band at 575 cm−1, Cu O at 438 cm−1 and the
broad peak at 3432 cm−1 for surface O H groups confirmed the
structure of prepared copper ferrite nanoparticles (see supporting
information).
TEM image was also used to further characterization of the mor-
phology and structure of CuF2O4 nanoparticles. As can be seen
in Fig. 2, CuF2O4 nanoparticles are mostly spherical and cubic,

22
M. Gholinejad et al. / Journal of Molecular Catalysis A: Chemical 386 (2014) 20–27
Table 1
The effects of various solvents in the copper ferrite nanoparticles catalyzed thioetherification of iodobenzene using thiourea and benzyl bromide in wet PEG 200.
Entry
Solvent
Isolated yield (%)
1
2
3
4
5
Toluene
1,4-dioxane
DMF
H2O
PEG(200)
12
43
69
48
92
1,4-dioxane in the coupling of iodobenzene (1 mmol), benzyl bro-
mide (1.1 mmol) and thiourea (1.2 mmol) as a model reaction in the
presence of CuFe2O4 (0.05 mmol) and potassium carbonate
(4.0 mmol). The results indicate that polyethylene glycol (200) was
the best solvent for this reaction (Table 1, entry 5). Polyethylene
glycol is a non-toxic, nonflammable, thermally stable, recoverable
and bio-compatible solvent which is often used in cosmetics, drugs
and food additives [98,99].
The scope of this methodology was further extended for
thioetherification of various aryl iodides and bromides using dif-
ferent alkyl bromides and thiourea in the presence of copper ferrite
nanoparticles and K2CO3 in the wet polyethylene glycol (Table 2).
Among the various substituted aryl iodides, both deactivated (elec-
tron rich) and activated (electron-poor) substrates were converted
efficiently to the desired products in excellent yields (entries 1–11).
Reaction of less reactive aryl bromides were preferentially per-
formed at 100 ◦C under otherwise reaction condition similar to aryl
iodides. Notably, the method is particularly effective for coupling
reaction involving highly challenging heterocyclic aryl bromides,
affording the corresponding thioethers in excellent yields (Table 2,
entries 21–22).
Fig. 1. XRD pattern of prepared CuFe2O4 nanoparticles.
almost mono-disperse and have an average diameter of about
20–30 nm.
The catalytic activity of prepared CuF2O4 nanoparticles was
evaluated in thioarylation reaction of aryl halides using thiourea
and alkyl bromides. We focused our initial investigation on effect
of various types of solvents such as water, DMF, PEG, toluene, and
In continue, the separation of CuFe2O4 nanoparticles from the
reaction mixture was studied using external magnetic rod. We
have studied the possibility of recycling of the catalyst from the
Fig. 2. TEM images for CuFe2O4 nanoparticles.

M. Gholinejad et al. / Journal of Molecular Catalysis A: Chemical 386 (2014) 20–27
23
Table 2
Copper ferrite nanoparticles catalyzed thioetherification of different aryl iodides and bromides using thiourea and alkyl halides in wet PEG 200.
Entries
1
ArX
R
Time (h)
12
Producta
Yield (%)b
TON/TOF (h−1
18.4/1.5
)
Benzyl
92
2
3
Butyl
12
12
90
86
18/1.5
Cyclohexyl
17.2/1.4
4
5
Benzyl
12
12
90
92
18/1.5
Butyl
18.4/1.5
6
7
Benzyl
Benzyl
12
15
86
88
17.2/1.4
17.6/1.2
8
Cyclohexyl
15
86
17.2/1.1
9
Cyclopentyl
12
89
17.8/1.5

24
M. Gholinejad et al. / Journal of Molecular Catalysis A: Chemical 386 (2014) 20–27
Table 2 (Continued)
Entries
10
ArX
R
Time (h)
12
Producta
Yield (%)b
TON/TOF (h−1
18/1.5
)
Butyl
90
11
Butyl
10
93
18.6/1.9
12
13
Benzyl
20
20
82
84
16.4/0.8
16.8/0.8
Butyl
14
Benzyl
20
80
16/0.8
15
Benzyl
20
91
18.2/0.9
16
Butyl
10
93
18.6/1.9
17
Cyclohexyl
12
80
16/1.3

M. Gholinejad et al. / Journal of Molecular Catalysis A: Chemical 386 (2014) 20–27
25
Table 2 (Continued)
Entries
18
ArX
R
Time (h)
Producta
Yield (%)b
TON/TOF (h−1
)
Cyclopentyl
12
84
16.8/1.4
19
Hexyl
12
89
17.8/1.5
20
Octyl
12
15
84
92
16.8/1.4
18.4/1.2
21
22
Benzyl
Hexyl
Butyl
15
24
87
73
17.4/1.2
14.6/0.6
23
a
Reaction conditions: ArX (1 mmol), RBr (1.1 mmol), thiourea (1.2 mmol), CuFe2O4 (5 mol%), K2CO3 (4.0 mmol), H2O (0.3 mL), and PEG (2 mL).
Yields are isolated.
b
reaction of iodobenzene with benzyl bromide and thiourea in the
wet polyethylene glycol. The results indicated that the process is
highly simple and catalyst can be completely separated from the
reaction mixture (see supporting information). After completion
of the reaction, the catalyst was separated by a magnetic rod and
was reused for the subsequent reaction for five consecutive runs
under restoring of catalytic activity of catalyst (Fig. 3). AAS analysis
of recycled copper ferrites after five runs indicated no decrease in
the content of Cu and no leached Cu was observed in the reaction
medium after each cycle.
Finally, we have studied application of copper ferrite nanopar-
ticles in one pot synthesis of symmetrical diaryl trithiocarbonates
using aryl iodides, carbon disulfide and sodium sulfide under
heterogeneous reaction condition. The reactions proceeded well
and desired products were obtained in high to excellent yields
(Table 3).
Fig. 3. Recycling of the catalyst for the reaction of iodobenzene with benzyl bromide
and thiourea in wet polyethylene glycol.

26
M. Gholinejad et al. / Journal of Molecular Catalysis A: Chemical 386 (2014) 20–27
Table 3
CuFe2O4 catalyzed one-pot synthesis of symmetrical diaryl trithiocarbonates.
Entry
ArI
Producta
Yield (%)b
TON/TOF (h−1
)
1
2
3
89
80
83
17.8/1.5
16/1.3
16.6/1.4
4
85
17/1.4
5
81
86
16.2/1.35
17.2/1.4
6
a
Reaction conditions: Na2S (1.1 mmol), CS2 (5 mmol), ArI (2 mmol), CuFe2O4 (12 mg, 5 mol%), and DMF (2 mL).
Yields are isolated.
b
4. Conclusions
Appendix A. Supplementary data
In conclusion, in this article we have prepared copper fer-
rite nanoparticles with the average size of 20–30 nm and
studied its catalytic activity for one-pot odorless thioetherifi-
cation of aryl bromides and iodides using alkyl bromides and
thiourea. The catalyst was also successfully applied for one-
pot synthesis of symmetrical diaryl trithiocarbonates from the
reaction of aryl iodides, carbon disulfide and sodium sulfide
under hetrogenous reaction condition. Copper ferrite nanoparti-
cles are recoverable by external magnet and we have recycled
catalyst for five consecutive runs with retention of catalyst activ-
ity.
Supplementary data associated with this article can be
found, in the online version, at http://dx.doi.org/10.1016/j.molcata.
2014.02.006.
References
[1] G. Ertl, H. Knözinger, J. Weitkamp, Handbook of heterogeneous catalysis, Wiley-
VCH, Weinheim, 1997.
[2] J. Zhou, Z. Dong, H. Yang, Z. Shi, X. Zhou, R. Li, Appl. Surf. Sci. 279 (2013)
360–366.
[3] X. Jin, K. Zhang, J. Sun, J. Wang, Z. Dong, R. Li, Catal. Commun. 26 (2012) 199–203.
[4] A.N. Ay, N.V. Abramova, D. Konuk, O.L. Lependina, V.I. Sokolov, B. Zümreoglu-
Karan, Inorg. Chem. Commun. 27 (2013) 64–68.
[5] J. Hu, Y. Wang, M. Han, Y. Zhou, X. Jiang, P. Sun, Catal. Sci. Technol. 2 (2012)
2332–2340.
[6] Y. Zhang, Z. Li, W. Sun, C. Xia, Catal. Commun. 10 (2008) 237–242.
[7] M.J. Aliaga, D.J. Ramon, M. Yus, Org. Biomol. Chem. 8 (2010) 43–46.
[8] F. Nador, M.A. Volpe, F. Alonso, A. Feldhoff, A. Kirschning, G. Radivoy, Appl.
Catal. A 455 (2013) 39–45.
[9] T. Zeng, L. Yang, R. Hudson, G. Song, A.R. Moores, C.J. Li, Org. Lett. 13 (2011)
442–445.
Acknowledgments
The authors are grateful to Institute for Advanced Studies in
Basic Sciences (IASBS) Research Council and Iran National Science
Foundation (INSF-Grant number of 90007432) for support of this
work.
[10] T. Ramani, P. Umadevi, K.L. Prasanth, B. Sreedhar, Eur. J. Org. Chem. (2013)
6021–6026.

M. Gholinejad et al. / Journal of Molecular Catalysis A: Chemical 386 (2014) 20–27
27
[11] M.Z. Kassaee, E. Motamedi, B. Movassagh, S. Poursadeghi, Synthesis 45 (2013)
2337–2342.
[54] J. Mondal, A. Modak, A. Dutta, A. Bhaumik, Dalton Trans. 40 (2011) 5228–5235.
[55] J. Mondal, N. Salam, A. Bhaumik, J. Nanosci. Nanotechnol. 13 (2013) 4883–4895.
[56] A. Kamal, V. Srinivasulu, J.N.S.R.C. Murty, N. Shankaraiah, N. Nagesh, T.S. Reddy,
A.V.S. Rao, Adv. Synth. Catal. 355 (2013) 2297–2307.
[57] P. Zhao, H. Yin, H. Gao, C. Xi, J. Org. Chem. 78 (2013) 5001–5006.
[58] F. Wang, C. Chen, G. Deng, C. Xi, J. Org. Chem. 77 (2012) 4148–4151.
[59] H. Firouzabadi, N. Iranpoor, A. Samadi, Tetrahedron Lett. 55 (2014) 1212–1217.
[60] C.S. Bryan, J.A. Braunger, M. Lautens, Angew. Chem. Int. Ed. 48 (2009)
7064–7068.
[12] I. Yavari, S. Beheshti, Helv. Chim. Acta 94 (2011) 1825–1830.
[13] R. Cano, M. Yus, D.J. Ramón, Tetrahedron 69 (2013) 7056–7065.
[14] R. Martínez, D.J. Ramón, M. Yus, Org. Biomol. Chem. 7 (2009) 2176–2181.
[15] E. Kim, S. Kim, B.M. Kim, Bull. Korean Chem. Soc. 32 (2011) 3183–3186.
[16] M.M. Mojtahedi, M.S. Abaee, T. Alishiri, Tetrahedron Lett. 50 (2009) 2322–2325.
[17] H. Firouzabadi, N. Iranpoor, M. Gholinejad, J. Hoseini, Adv. Synth. Catal. 353
(2011) 125–132.
[18] N. Panda, A.K. Jena, S. Mohapatra, Chem. Lett. 40 (2011) 956–958.
[19] M.L. Kantam, J. Yadav, S. Laha, S. Jha, Synlett (2009) 1791–1794.
[20] Y.L.N. Murthy, B.S. Diwakar, B. Govindh, K. Naglakashmi, I.V.K. Viswanath, R.
Singh, J. Chem. Sci. 124 (2012) 639–645.
[21] R. Zhang, J. Liu, S. Wang, J. Niu, C. Xia, W. Sun, ChemCatChem 3 (2011) 146–149.
[22] V. Avudoddi, V.K.G. Palle, V.R. Pallapothula, Eur. J. Chem. 3 (2012) 298–304.
[23] S. Yang, C. Wu, H. Zhou, Y. Yang, Y. Zhao, C. Wang, W. Yang, J. Xua, Adv. Synth.
Catal. 355 (2013) 53–58.
[61] M.A. Fernández-Rodríguez, Q. Shen, J.F. Hartwig, J. Am. Chem. Soc. 128 (2006)
2180–2181.
[62] Z. Jiang, J. She, X. Lin, Adv. Synth. Catal. 351 (2009) 2558–2562.
[63] C.C. Eichman, J.P. Stambuli, J. Org. Chem. 74 (2009) 4005–4008.
[64] C.-F. Fu, Y.-H. Liu, S.-M. Peng, S.-T. Liu, Tetrahedron 66 (2010) 2119–2122.
[65] G.Y. Li, Angew. Chem. Int. Ed. 40 (2001) 1513–1516.
[66] M.A. Fernandez-Rodriguez, Q. Shen, J.F. Hartwig, Chem. Eur. J. 12 (2006)
7782–7796.
[24] S. Yang, W. Xie, H. Zhou, C. Wu, Y. Yang, J. Niu, W. Yang, J. Xu, Tetrahedron 69
(2013) 3415–3418.
[25] K. Swapna, S.N. Murthy, M.T. Jyothi, Y.V.D. Nageswar, Org. Biomol. Chem. 9
(2011) 5989–5996.
[26] N. Panda, A.K. Jena, S. Mohapatra, Appl. Catal. A 433–434 (2012) 258–264.
[27] R. Zhang, C. Miao, Z. Shen, S. Wang, C. Xia, W. Sun, ChemCatChem 4 (2012)
824–830.
[28] K. Swapna, S.N. Murthy, Y.V.D. Nageswar, Eur. J. Org. Chem. (2011) 1940–1946.
[29] K.H.V. Reddy, G. Satish, K. Ramesh, K. Karnakar, Y.V.D. Nageswar, Chem. Lett.
41 (2012) 585–587.
[67] M.A. Fernandez-Rodrieguez, J.F. Hartwig, J. Org. Chem. 74 (2009) 1663–1672.
[68] T. Dahl, C.W. Tornøe, B. Bang-Andersen, P. Nielsen, M. Jørgensen, Angew. Chem.
Int. Ed. 47 (2008) 1726–1728.
[69] L. Wang, W.-Y. Zhou, S.-C. Chen, M.-Y. He, Q. Chen, Adv. Synth. Catal. 354 (2012)
839–845.
[70] V. Percec, J.Y. Bae, D.H. Hill, J. Org. Chem. 60 (1995) 6895–6903.
[71] Y.C. Wong, T.T. Jayanth, C.H. Cheng, Org. Lett. 8 (2006) 5613–5616.
[72] V.P. Reddy, K. Swapna, A.V. Kumar, K.R. Rao, J. Org. Chem. 74 (2009) 3189–3191.
[73] V.P. Reddy, A.V. Kumar, K. Swapna, K.R. Rao, Org. Lett. 11 (2009) 1697–1700.
[74] J.R. Wu, C.H. Lin, C.F. Lee, Chem. Commun. (2009) 4450–4452.
[75] A. Correa, M. Carril, C. Bolm, Angew. Chem. Int. Ed. 47 (2008) 2880–2883.
[76] M. Bandaru, N.M. Sabbavarpu, R. Katla, V.D.N. Yadavalli, Chem. Lett. 39 (2010)
1149–1151.
[30] D. Kundu, N. Mukherjee, B.C. Ranu, RSC Adv. 3 (2013) 117–125.
[31] N. Panda, A.K. Jena, S. Mohapatra, S.R. Rout, Tetrahedron Lett. 52 (2011)
1924–1927.
[32] E. Block, Reactions of Organosulfur Compounds, Academic Press, New York,
1978.
[33] P.I. Beletskaya, P.A. Valentine, Chem. Rev. 111 (2011) 1596–1636.
[34] G. Liu, J.R. Huth, E.T. Olejniczak, R. Mendoza, P. DeVries, S. Leitza, E.B. Reilly,
G.F. Okasinski, E. Nielsen, S.W. Fesik, T.W. von Geldern, J. Med. Chem. 44 (2001)
1202–1210.
[77] G.-p. Lu, C. Cai, Adv. Synth. Catal. 355 (2013) 1271–1276.
[78] G.-P. Lu, C. Cai, Green Chem. Lett. Rev. 5 (2012) 481–485.
[79] Z. Li, F. Ke, H. Deng, H. Xu, H. Xiang, X. Zhau, Org. Biomol. Chem. 11 (2013)
2943–2946.
[80] H. Firouzabadi, N. Iranpoor, M. Abbasi, Adv. Synth. Catal. 351 (2009) 755–766.
[81] H. Firouzabadi, N. Iranpoor, M. Gholinejad, Adv. Synth. Catal. 352 (2010)
119–124.
[35] S.F. Nielsen, E.Ø. Nielsen, G.M. Olsen, T. Liljefors, D. Peters, J. Med. Chem. 43
(2000) 2217–2226.
[82] M. Gholinejad, Eur. J. Org. Chem. (2013) 257–259.
[36] G. Liu, J.R. Huth, E.T. Olejniczak, R. Mendoza, P. DeVries, S. Leitza, E.B. Reilly, G.F.
Okasinski, S.W. Fesik, T.W. von Geldern, J. Med. Chem. 44 (2001) 1202–1210.
[37] A. Gangjee, Y. Zeng, T. Talreja, J.J. McGuire, R.L. Kisliuk, S.F. Queener, J. Med.
Chem. 50 (2007) 3046–3053.
[38] A.-M. Faucher, P.W. White, C. Brochu, C.G. Maitre, J. Rancourt, G. Fazal, J. Med.
Chem. 47 (2004) 18–21.
[39] Y. Wang, W. Chang, V.R. Greenlee, Bioorg. Med. Chem. Lett. 11 (2001) 891–894.
[40] S.W. Kadlor, V.J. Kalish, J.F. Davies, J. Med. Chem. 40 (1997) 3979–3985.
[41] A.V. Bierbeek, M. Gingras, Tetrahedron Lett. 39 (1998) 6283–6286.
[42] J.R. Campbell, J. Org. Chem. 29 (1964) 1830–1833.
[83] H. Firouzabadi, N. Iranpoor, M. Gholinejad, A. Samadi, J. Mol. Catal. A: Chem.
377 (2013) 190–196.
[84] M. Kuhn, F.C. Falk, J. Paradies, Org. Lett. 13 (2011) 4100–4103.
[85] H.-Y. Niu, C. Xia, G.-R. Qu, S. Wu, Y. Jiang, X. Jin, H.-M. Guo, Chem. Asian J. 7
(2012) 45–49.
[86] S.A. Tao, A.L.N. Zhao, S. Yang, X. Liu, J. Zhou, W. Liu, j. Zhao, Synlett (2011)
134–138.
[87] F. Ke, Y. Qu, Z. Jiange, Z. Li, D. Wu, X. Zhou, Org. Lett. 13 (2011) 454–457.
[88] K.H.V. Reddy, V.P. Reddy, A.A. Kumar, G. Kranthi, Y.V.D. Nageswar, Beilstein J.
Org. Chem. 7 (2011) 886–891.
[43] F.Y. Kwong, S.L. Buchwald, Org. Lett. 4 (2002) 3517–3520.
[44] C.G. Bates, R.K. Gujadhur, D. Venkataraman, Org. Lett. 4 (2002) 2803–3805.
[45] Y.-J. Chen, H.H. Chen, Org. Lett. 8 (2006) 5609–5612.
[46] M. Kuhn, F.C. Falk, J. Paradies, Org. Lett. 13 (2011) 4100–4103.
[47] M. Carril, R. SanMartin, E. Dominguez, I. Tellitu, Chem. Eur. J. 13 (2007)
5100–5105.
[48] N. Taniguchi, T. Onami, J. Org. Chem. 69 (2004) 915–920.
[49] C.G. Bates, P. Saejueng, M.Q. Doherty, D. Venkataraman, Org. Lett. 6 (2004)
5005–5008.
[89] L. Xiaokang, T. Yuan, J. Chen, Chin. J. Chem. 30 (2012) 651–655.
[90] N. Park, K. Park, M. Jang, S. Lee, J. Org. Chem. 76 (2011) 4371–4378.
[91] D.J.C. Prasad, G. Sekar, Org. Lett. 13 (2011) 1008–1011.
[92] N. Park, Y. Heo, M.R. Kumar, Y. Kim, K.H. Song, S. Lee, Eur. J. Org. Chem. (2012)
1984–1993.
[93] M. Soleiman-Beigi, F. Mohammadi, Tetrahedron Lett. 53 (2012) 7028–7030.
[94] X.M. Wu, W.Y. Hu, Chin. Chem. Lett. 23 (2012) 391–394.
[95] C. Chen, Y. Xie, L. Chu, R.-W. Wang, X. Zhang, F.-L. Qing, Angew. Chem. 124
(2012) 2542–2545.
[50] P.S. Herradura, K.A. Pendola, R.K. Guy, Org. Lett. 2 (2000) 2019–2022.
[51] C. Savarin, J. Srogl, L.S. Liebeskind, Org. Lett. 4 (2002) 4309–4312.
[52] H.-J. Xu, Y.-F. Liang, X.-F. Zhoua, Y.-S. Feng, Org. Biomol. Chem. 10 (2012)
2562–2568.
[53] J. Mondal, A. Modak, A. Dutta, S. Basu, S.N. Jha, D. Bhattacharyya, A. Bhaumik,
Chem. Commun. 48 (2012) 8000–8002.
[96] Y. Jiang, Y. Qin, S. Xie, X. Zhang, J. Dong, D. Ma, Org. Lett. 11 (2009) 5250–5253.
[97] N. Panda, A.K. Jena, S. Mohapatra, S.R. Rout, Tetrahedron Lett. 52 (2011)
1924–1927.
[98] C.K.Z. Andrade, L.M. Alves, Curr. Org. Chem. 9 (2005) 195–218.
[99] J. Chen, S.K. Spear, J.G. Huddleston, R.D. Rogers, Green. Chem. 7 (2005) 64–82.