Metal Organic Framework 199- Catalyzed Domino Sulfur-Coupling and Transfer Reactions: The Direct Synthesis of Symmetric Diaryl Disulfides from Aryl Halides

Article abstract of DOI:10.1007/s10562-016-1768-8

Abstract: A highly porous metal–organic framework Cu₃ BTC₂ (copper(II)-benzene-1,3,5-tricarboxylate) that known as MOF-199 was synthesized, and characterized by common methods including, FT-IR, XRD, EDX, SEM and then used as an efficient and recyclable catalyst for the direct synthesis of symmetric organic disulfides. A variety of symmetric diaryl disulfides with high chemoselectivity can be obtained by domino reaction of aryl halides (and tosylates) and potassium 5-methyl-1,3,4-oxadiazole-2- thiolate, as the base and sulfur-transfer reagent, in the presence of MOF-199. Graphical Abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s10562-016-1768-8

Catal Lett
DOI 10.1007/s10562-016-1768-8
Metal Organic Framework 199- Catalyzed Domino
Sulfur-Coupling and Transfer Reactions: The Direct
Synthesis of Symmetric Diaryl Disulfides from Aryl Halides
Mohammad Soleiman-Beigi1 Fariba Mohammadi1
•
Received: 16 April 2016 / Accepted: 12 May 2016
Ó Springer Science+Business Media New York 2016
Abstract A highly porous metal–organic framework Cu3
BTC2 (copper(II)-benzene-1,3,5-tricarboxylate) that
Graphical Abstract
known as MOF-199 was synthesized, and characterized by
common methods including, FT-IR, XRD, EDX, SEM and
then used as an efficient and recyclable catalyst for the
direct synthesis of symmetric organic disulfides. A variety
of symmetric diaryl disulfides with high chemoselectivity
can be obtained by domino reaction of aryl halides (and
tosylates) and potassium 5-methyl-1,3,4-oxadiazole-2-
thiolate, as the base and sulfur-transfer reagent, in the
presence of MOF-199.
N N
O
S K
Ar
Arx
Ar
+
CH3
S
S
MOF-199
Keywords Metal–organic framework Á MOF-199 Á Direct
synthesis Á Diaryl disulfides Á Sulfur-transfer reagent
1 Introduction
The past few decades have witnessed the unprecedented
explosion of a new research in the preparation, character-
ization, and study of materials known as metal–organic
frameworks (MOFs) [1]. The first reports on MOFs,
coordination polymers or supramolecular structures from
the late 1950s [2] and early 1960s [3–7]. After it was with
an exponential growth in the number of research papers
and reviews appearing in the chemical literature [8, 9].
MOFs have exceptional porosity, very high adsorption
capacities, specific surface areas and pore sizes [10]. Their
Electronic supplementary material The online version of this
article (doi:10.1007/s10562-016-1768-8) contains supplementary
material, which is available to authorized users.
& Mohammad Soleiman-Beigi
SoleimanBeigi@yahoo.com;
m.soleimanbeigi@mail.ilam.ac.ir
1
Department of Chemistry, Basic of Sciences Faculty, Ilam
University, Ilam, PO Box 69315-516, Iran
123

M. Soleiman-Beigi, F. Mohammadi
porosity is very higher than zeolites [11]. In contrast to
other nano-structured compounds, many MOFs display a
excellent flexibility and respond to the presence of external
stimuli [12]. Some MOFs are unexpectedly thermo- (above
250 °C in several cases) and chemo-stable [13, 14].
MOFs have a wide range of potential uses including
catalysis, gas storage [15] and separations [16], drug stor-
age and delivery, sensors and luminescence, templated low
dimensional material preparation [17–19]. Also, these
materials application in energy technologies such as fuel
cells, super capacitors, and catalytic conversions (indus-
trial-scale production, and application) [20, 21].
thiosemicarbazide [60], sodium sulfide [61, 62], sulfur
[63–67], carbon disulfide [68–70], morpholin-4-ium mor-
pholine-4-carbodithioate [71, 72], thioacetamide [73],
sodium thiosulfate [74, 75], potassium xanthogenate
[76, 77], tetrathiomolybdate [78] and tetrathiotungstate [79].
In continuation of our efforts in apply of sulfur transfer
reagents to direct synthesis of organosulfur compounds [56,
57],we offer potassium 5-methyl-1,3,4-oxadiazole-2-thiolate
(1) as a new sulfur transfer reagent in previous works
[80, 81]. That is an odorless, stable, nontoxic and environ-
mentally friendly basic solid reagent which can be easily
prepared and handled. It has been played, at these works,
both sulfur transfer reagent and base roles efficiently.
In the field of catalysis, MOFs have been employed for
variety of organic conversion, including Suzuki cross-
coupling [22], Sonogashira reaction [23], Friedel–Crafts
alkylation and acylation [24], three-component coupling
reaction of aldehyde, alkyne, and amine [25], the Biginelli
reaction [26], Knoevenagel condensation [27], cycloaddi-
tion of CO2 with epoxides [28], alkene epoxidation [29],
oxidation [30], transesterification reaction [31] and
hydrolysis of ammonia borane [32]. Specifically, Cu3BTC2
(copper(II)-benzene-1,3,5-tricarboxylate) is one of the best
studied MOFs that this structure has first been synthesized
and characterized in 1999 by Chui et al., who denominated
the structure as ‘‘HKUST-1’’ [33–35].
2 General Methods and Materials
All reagents and starting materials were obtained commerical
from Sigma–Aldrich and Merck. Fourier transform infrared
(FT-IR) spectra were obtained on a bruker VERTEX 70
instrument, with samples being dispersed on potassium bro-
mide pallets. The particle size and morphology were inves-
tigated by a JEOL JEM-2010 scanning electron microscopy
(SEM). X-ray powder diffraction (XRD) data was obtained
using a Philips PW 1800 diffractometer with Cuka radiation
(wavelength 1.54 nm, 40 kV).
In this work, we wish to report the application of MOF-
199 as an efficient, highly porous and recyclable catalyst for
the direct synthesis of diaryl disulfides by domino cross-
coupling reaction of a sulfur transfer reagent and aryl halides.
Organic disulfides have attracted much attention
because of their various biological, synthetic and industrial
applications [36]. The S–S bond being an important part of
the macromolecules, mainly present in functional proteins
like enzymes, peptides, antibodies and hormones. It cause
conformational constraints and increase the stability of
such molecules [37]. Disulfides are useful reagents in a
wide range of pharmaceutical and agrochemical com-
pounds [38]. In addition they have been used for prepara-
tion of catenanes [39], dynamic combinatorial libraries
[40], carceplexes [41], rotaxanes [42], dendrimers [43],
macrocycles [44], micelles [45] self-assembled monolayers
[46] and monolayer-protected clusters [47].
2.1 Synthesis of MOF-199
The procedure to prepare MOF-199 was according to Ref
[82, 83]. Benzenetricarboxylic acid (500 mg, 2.38 mmol)
was mixed in 12 mL of a 1:1:1 mixture of DMF/EtOH/
H2O. Cu(OAc)2ÁH2O (860 mg, 4.31 mmol) was mixed
with 12 mL of the same solvent and the mixtures were
combined with stirring. Triethylamine (0.5 mL) was added
to the reaction mixture, which was stirred for 24 h. The
product was collected by filtration, washed twice with
DMF (25 ml), and finally dried.
2.2 Symmetrical Diaryl Disulfides Synthesis;
Typical Experimental Procedure
The synthesis of organic disulfide compounds by the
oxidation of thiol derivatives has become a common method
[48–50]. However, potential health and environmental risks
associated with them, moreover difficulty in working with
thiols, have persuaded organic chemists to use sulfur-trans-
fer reagents to overcome these disadvantages [51–54].
Many sulfur-containing compounds have been evaluated
for their ability to transfer sulfur, and Sulfur transfer
reactions in aim to the direct synthesis of sulfides and
disulfides in recent years. Some of these reagents include:
potassium thiocyanate [53, 55], thiourea [54, 56–59],
A
mixture of iodobenzene (2.0 mmol), potassium
5-methyl-1,3,4-oxadiazole-2-thiolate (1) (3.0 mmol),
MOF-199 (8 mg, 10 % mol) were added to a flask con-
taining 2 mL DMF/H2O (20:1), The reaction continued at
130 °C under atmospheric conditions until completion.The
reaction progress was controlled by thin-layer chromatog-
raphy. The reaction mixture was then filtered. The filtrate
was evaporated under vacuum, CH2Cl2 (20 ml) was added
and the mixture was washed with H2O (2 9 15 ml). The
organic layer was dried over anhydrous Na2SO4. The sol-
vent was evaporated to give the crude diaryl disulfide,
123

Metal Organic Framework 199- Catalyzed Domino Sulfur-Coupling and Transfer Reactions: The…
Table 1 Optimization of the reaction conditions
Entry
MOF-199 (mg)
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
–
24
24
10
4
N.R
82
96
95
95
97
85
69
4
6
8
10
12
12
12
4
4
3
2
Reaction conditions PhI (2.0 mmol), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate (1) (3 mmol), in 2 ml DMF at 130 °C under air. N.R no
reaction
Entry
Temp (°C)
Time (h)
Yield (%)
9
25
24
24
24
4
Trace
64
10
11
12
80
110
130
87
95
Reaction conditions PhI (2.0 mmol), MOF-199 (8 mg), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate (1) (3 mmol), in 2 ml DMF
Entry
Temp (°C)
Time (h)
Yield (%)
13
14
15
16
H2O
24
24
24
4
Trace
68
PEG
Ethanol
DMF
Trace
95
Reaction conditions PhI (2.0 mmol), MOF-199 (8 mg), potassium 5-methyl-1,3,4-oxadiazole-2-thiolate (1) (3 mmol), at 130 °C in 2
which was purified by plate chromatography (silica gel,
n-hexane–ethyl acetate, 20:1).
According to the results shown in Table 1, the reaction
no proceeded in the absence of MOF-199 and was found
that increasing the amount of MOF-199 up to 8 mg let to
increase rate of the reaction, but increasing amount of
catalyst more of 8 mg has not been perceptible alteration in
the progress of reaction (Table 1, entries 1–6). Tempera-
ture significantly affected the rate of the reaction. The
reaction yield and rate increased with temperature up to
130 °C (Table 1, entries 9–12). DMF was found the most
effective solvent (Table 1, entries 13–16). Diphenyl
disulfide was obtained as the sole product in all reactions.
A large number of symmetrical diaryl disulfides was
synthesized in the presence of 8 mg from MOF-199, using
3 equiv of potassium 5-methyl-1,3,4-oxadiazole-2-thiolate
(1) at 130 °C under normal atmospheric conditions and
stopped the reaction immediately after full conversion was
reached (Table 2).
All spectra of the diaryl disulfides are mentioned in the
electronic supplementary material.
3 Results and Discussion
The reaction of iodobenzene with potassium 5-methyl-
1,3,4-oxadiazole-2-thiolate (1) in the presence of MOF-199
was studied under normal atmospheric conditions in order
to optimize the reaction conditions in terms of temperature,
amount of MOF-199 and solvent (Scheme 1).
N N
MOF-199
Ar
S
2 Arx
+ 3
CH3
S K
O
S
2
Ar
°
DMF/H2O, 130 C
(1)
The reaction efficiency for the synthesis of diaryl
disulfides from various aryl halides (and tosylates) was
Scheme 1 Symmetric diaryl disulfides synthesis
123

M. Soleiman-Beigi, F. Mohammadi
examined. As can be seen, aryl iodides and aryl bromides
were more effective than aryl chlorides and aryl tosylates
(Table 2, entries 1–4). Symmetric diaryl disulfides with
different functional groups, such as CH3, OCH3, NO2,
NH2, Br, Cl and F were also synthesized in good to
excellent yields.
Table 2 MOF-199 catalyzed; the direct synthesis of symmetrical
diaryl disulfides from aryl halides (and tosylates)
Entry
Ar-X
Product a
Time Yieldb
(h)
4.5
6
(%)
98
I
S
S
As a general result, under the optimal conditions men-
tioned above, higher rate in reactions were obtained with
substituted groups such as NO2, Br and F (conversion
100 %, Table 2, entries 9,11 and 18). But reactions were
slowly complete in the presence of OCH3 and NH2 groups
(Table 2, entries15–17).
1
98
Br
S
S
S
S
S
S
2
3
OTS
12
18
96
92
Previously, we used Cu salts to the direct synthesis
disulfides in a novel, one-pot and efficient method without
the need to addition of base and ligand.
Cl
4
5
6
While, it required comparatively much amount of Cu
salts [80]. In order to overcome this disadvantage, Nickel
chloride was used as a more reactive catalyst successfully,
however ethylene glycol and potassium hydroxide were
used as ligand and base, respectively [81]. Finally, the
protocol herein was developed by using a catalytic amount
of MOF-199 under a ligand-free and additional base-less in
normal conditions. Also high chemoselectivity of the
reaction is another desirable feature of this protocol, for
example in the reaction between of 1-bromo-4-iodoben-
zene and potassium 5-methyl-1,3,4-oxadiazole-2-thiolate
(1) under optimized reaction conditions, bis-(4-bro-
mophenyl) disulfide was the sole product (98 % yield),
while that was generated as the main product with 55 and
78 % yields in the presence of CuCl and NiCl2Á6H2O,
respectively. In the presence of CuCl and NiCl2.6H2O bis-
(4-iodophenyl) disulfide was obtained as a side product.
Additionally, this procedure works fine with all kinds of
aryl (heteroaryl) halides as well as aryl tosylates mostly
with more than 70 % isolated yield (Table 3).
CH
S
3
I
CH
S
4.25
6
98
96
3
CH
3
I
S
S
Br
S
S
7
8
10
10
90
81
S
S
S
OTS
Br
I
S
3.25
98
9
Br
Br
Cl
F
3.1 Characterization of MOF-199
Br
6
4
6
83
86
84
S
S
S
S
10
11
12
Cl
Fourier transform infrared spectra (Fig. 1a) shows
absorption in the waves numbers 3423, 1640 and
1442 cm-1 that they are related to water molecule, car-
bonyl group of Benzenetricarboxylic acid and double
bonds of benzene, respectively (Fig. 1a). To confirm the
recoverability and reusability of the MOF-199 in the
preparation of dichalcogenides reaction, the recovered
MOF-199 catalyst was also characterized by XRD, FT-IR,
and SEM. The FT-IR spectra of the reused MOF-199 after
the fifth run revealed a similar absorption as compared to
that of the fresh catalyst (Fig. 1b).
Cl
F
F
Br
F
F
F
S
S
S
S
I
S
S
S
S
6.5
81
76
S
S
S
S
Br
13
14
S
S
X-ray powder diffraction patterns (Fig. 2a) shows the
presence of the main diffraction peak in the 2h = 11.
Moreover, XRD result of the reused catalyst after the fifth
run exhibited that the MOF-199 could maintain its
S
7.25
Cl
123

Metal Organic Framework 199- Catalyzed Domino Sulfur-Coupling and Transfer Reactions: The…
Table 2 continued
Entry
Ar-X
Product a
Time Yieldb
(h)
(%)
NH2
OMe
I
I
S
S
15
24
76
NH
NH2
MeO
2
S
S
24
24
96
72
16
17
MeO
MeO
I
S
S
OMe
Fig. 1 FT-IR spectra of the fresh (a) MOF-199 (b) and reused
OMe
NO2
CH3
Br
1.75
12
56
84
S
S
18
19
NO2
CH3
NO2
CH3
Br
S
S
a
All the products are known compounds and were characterized by
comparison of NMR, GC-Mass spectral data and melting points with
those reported in the literature. bIsolated yield
b
Isolated yield
Fig. 2 X-ray powder diffractogram of the fresh (a) MOF-199 (b) and
reused
Table 3 Comparison of the Catalyzes; Cu, Ni and MOF
a
Percentage of production bis-(4-bromophenyl) disulfide from 1-
bromo-4-iodobenzene. b Ethlene glycol
Fig. 3 Leaching test indicated no contribution from homogeneous
catalysis of active copper species leaching into reaction solution for
the synthesis of disulfides
crystallinity during the course of the reaction, however
crystallinity is a little reduced after 5th recycling (Fig. 2b).
The experimental results clearly confirmed that almost
no further conversion was observed for the synthesis of
dichalcogenides and the preparation of this compounds can
only proceed in the presence of the solid MOF-199 cata-
lyst, and the contribution of leached active copper species
soluble in the solution, if any, was negligible (Fig. 3).
It also shows the incorporation of Cu metal inside the
framework organic and a uniform distribution of the par-
ticles throughout the framework, confirmed by EDX anal-
ysis (Fig. 4).
Scanning electron microscopy (Fig. 5) shows existence
crystales in nano-size. All of the data are similar to that of
123

M. Soleiman-Beigi, F. Mohammadi
reaction was performed in DMF at 130 °C, using the
2 mmol iodobenzene in the presence of 8 mg MOF-199
catalyst. After each run, the catalyst was separated from the
reaction mixture by simple decantation, and washed with
copious amounts of n-Hexan to remove any physisorbed
reagents. Then was dried under vacuum at 160 for 3 h, The
recovered MOF-199 catalyst was then reused in further
reaction under identical conditions to those of the first run.
It was found that the MOF-199 could be reused several
times without a significant degradation in catalytic activity.
It was observed that a conversion of 92 % for diaryld-
isulfide is still achieved in the 5th run. (Fig. 6).
Fig. 4 Energy-dispersive X-ray spectroscopy of the MOF-199
4 Conclusion
This work reports a simple, efficient and one-pot protocol
for the synthesis of symmetric diaryl disulfides from aryl
halides (and tosylates) by using potassium 5-methyl-1, 3, 4-
oxadiazole-2-thiolate (1) salt as a base and sulfurizing
reagent. Herein, a new application of MOF-199 as a
heterogeneous catalyst in these type cross-coupling reac-
tions is described.
MOF-199 is as a porous, recyclable and chemoselective
catalyst which is more efficient more economic, more
comprehensive, and more environmentally friendly than
previous catalyst.
Acknowledgments We acknowledge the financial support of Ilam
University Research Council.
Fig. 5 SEM micrograph of the MOF-199
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