Copper catalyzed synthesis of unsymmetrical diaryl sulfones from an arenediazonium salt and sodium p-toluenesulfinate

Article abstract of DOI:10.1039/c5ra10291j

Aryl sulfones have been for the first time synthesized by the reaction of sodium p-toluenesulfinate and arenediazonium salts using a CuI catalyzed homogeneous system. The developed protocol is a simple and efficient new route for the synthesis of diaryl sulfones with excellent product yields. The mild reaction conditions tolerate a range of functional groups. The best results were obtained with CuI, N,N′-dimethylethylenediamine, TBAI and K₂CO₃ in dimethyl sulfoxide at 100°C under an inert atmosphere.

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Copper catalyzed synthesis of unsymmetrical diaryl sulfones from
arenediazonium salt and sodium p-toluenesulfinate
Sitaram Haribhau Gund,a Radheshyam Suresh Shelkara and Jayashree Milind Nagarkar*a
Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
5
DOI: 10.1039/b000000x
Aryl sulfones have been first time synthesized by reaction of sodium pꢀtoluenesulfinate and
arenediazonium salts using CuI catalyzed homogeneous system. The developed protocol is simple and
efficient new route for synthesis of diaryl sulfones with excellent product yield. The mild reaction
conditions tolerate a range of functional groups. The best results were obtained with CuI, N,N’ꢀ
10 dimethylethylenediamine, TBAI and K2CO3 in Dimethyl sulfoxide at 100 °C under inert atmosphere.
sulfonylation of heterocycles with aryl sulfonyl chlorides via
metalꢀcatalyzed C–H bonds activation,9 Pdꢀ or Cuꢀcatalyzed
40 coupling reactions between sodium sulfinates and aryl halides or
aryl boronic acids10 and vinyl sulfones from terminal epoxides
and sodium sulfinates.11 Various catalysts have been developed
for the synthesis of sulfones.12 However, these methods have
some drawbacks such as use of toxic or expensive transition
45 metals, multiꢀstep synthesis, low functional group tolerance,
limited availability of substrates, low yields, use of expensive
aryl halides, longer reaction times, and dry reaction conditions.
Recently B. T. V. Srinivas et al. reported synthesis of diaryl
sulfones from various boronic acids using Cuꢀcatalyst.13 Fig.S1
50 depicts the various reported methods for the synthesis of aryl
sulfones.
1 Introduction
CarbonꢀSulphur (CꢀS) bond forming reactions gained importance
in organic synthesis, as these reactions are the key steps in the
formation of various biologically valuables compounds.1 Aryl
15 sulfones are the important class of sulfur containing moiety
which are found in many pharmaceuticals, agrochemicals and
polymeric compounds (Fig.1).2 Particularly, the bioactivity of
aryl sulfones has immense importance in medicinal chemistry.
Aryl sulfones show various pharmacological properties such as
20 antiꢀtumour, antiꢀinflammatory, and antiꢀfungal activities, and
also inhibit HIVꢀ1 reverse transcriptase.3 Sulfone derivatives
were found in cyclooxygenaseꢀ2 (COXꢀ2) inhibitors4 which
exhibit high antifungal and antibacterial activities.5 They also
exhibit interesting chemical properties6 and are useful as
25 intermediates in organic synthesis.7
An arenediazonium salt is currently attracting much attention
because of the ready availability of these compounds and the ease
55 with which they can be synthesized. They are more reactive than
aryl halides or boronic acids, making them good choice as
arylating agents. Arenediazonium salts can be used in a range of
various reactions, such as Suzuki–Miyaura,14 Stille,15
Sonogashira,16 or Mizoroki–Heck reactions.17 Here we report the
60 synthesis of aryl sulfones using arenediazonium salts with CuI
and N,N’ꢀdimethylethylenediamine ligand in DMSO at 100 °C
under inert atmosphere (Scheme 1).19
O
O
O
N
BF4
S
N
S
65
O
Na
L
CuI, 1, TBAI
DMSO, K2CO3,
100 °C, N2, 24h.
30
Fig. 1 Aryl sulfones containing molecules.
Scheme 1. Model reaction between sodium pꢀtoluenesulfinate
70 and arenediazonium salt.
This broad utility has prompted significant efforts toward the
synthesis of sulfone containing compounds. As a result of this,
35 various methods have been developed for the synthesis of aryl
sulfones such as nucleophilic substitution reaction of halide with
thiol, followed by oxidation of the corresponding sulphide,8
2 Results and discussion
Initially, various reaction conditions were optimized step by step
for the model reaction between sodium pꢀtoluenesulfinate and
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arenediazonium salt. Ligand plays a very crucial role in
homogeneous catalysis with respect to product yield. Therefore,
we carried out the model reaction with CuI as a catalyst in DMSO
using various ligands. Here we screened four ligands such as
aReaction conditions: Sodium pꢀtoluenesulfinate (1 mmol),
Arenediazonium salts (1.3 mol), Cu source (15 mol %), Ligand
(15 mol%), Additive (1.3 mmol), Base (3 mmol), Solvent (2 mL),
under N2. bIsolated yield. cWithout ligand.
5
N,N’ꢀdimethylethylenediamine
(L1),
N,N,N’,N’-
40
tetramethylethylenediamine (L2), bipyridine (L3) and 1,10ꢀ
phenanthroline (L4) for model reaction along with CuI catalyst
(Fig. S2). The obtained results are represented in Fig.S3. This
clearly shows that L1 is a superior ligand than others giving
We also examined the effect of the catalytic amount and ligand
concentration on the product yield of the model reaction by
varying the amount of catalyst and ligand from 10 to 20 mol%
(Fig. S4). Fig. S4 shows that increase in the catalyst and ligand
10 excellent product yield along with CuI. We examined various Cu 45 concentration from 10 to 15 mol% increases the yield of the
sources such as CuI, CuBr, Cu2O, Cu(OAc)2, CuSO4,
Cu(Phen)(PPh3)2NO3 and Cu(acac)2 for the model reaction of
sodium pꢀtoluenesulfinate and arenediazonium salt and found that
CuI is the best source of Cu as catalyst (Table 1, entries 1ꢀ7).
desired product. However increase in the catalyst and ligand
concentration up to 20 mol% did not increase the product yield
significantly. The amount of tetrabutylammonium iodide additive
was also optimized by varying its concentration from 1.2 to 1.4
15 Furthermore, we studied model reaction by using various solvents 50 mmol. It was clear from the results depicted in Fig. S5 that the
such as DMSO, DMF, toluene and H2O. DMSO solvent gave
maximum yield of desired product (Table 1, entries 1, 8ꢀ10). We
also studied the reaction in various bases and found K2CO3 as the
most suitable base amongst the other bases such as NaHCO3,
concentration of additive also plays an important role in the
reaction, and the optimal concentration of tetrabutylammonium
iodide for the model reaction was found to be 1.3 mmol. We also
evaluated the exact required time for the model arylation reaction
20 Na2CO3, K3PO4, Cs2CO3 and tBuONa (Table 1, entries 1, 11ꢀ15). 55 and the graph plotted in Fig. S6 clearly indicates that 24h is the
The solvation of K+ ion is greater than that of Na+ ion due to the
ionic size, which consequently increases the rate of reaction. In
this reaction we used TBAI (Tetrabutylammonium iodide),
TBAB (Tetrabutylammonium bromide), KI (Potassium iodide)
required time for the completion of reaction. All above
experiments reveal that the optimised reaction conditions are
Sodium pꢀtoluenesulfinate (1 mmol), Arenediazonium salt (1.3
mol), CuI (15 mol %), L1 (15 mol %), TBAI (1.3 mmol), K2CO3
25 and KBr (Potassium bromide) additives as halogen source to 60 (3 mmol), DMSO (2mL), 100 °C and 24h under inert atmosphere.
form halobenzene in situ18. The arylation reaction was more
efficient with the halogen source TBAI (Table 1, entries 1, 16ꢀ
18). The optimum temperature was found to be 100 °C for the
model reaction. Increase in temperature to 120 °C, did not
After optimizing parameters such as catalyst, ligand, solvent,
base, additive, concentration of catalyst, reaction temperature and
time, we further investigated the catalytic activity for the
coupling of structurally different arenediazonium salts and
30 improve the product yield. Significant decrease in the product 65 Sodium pꢀtoluenesulfinate and the results are summarized in
yield was observed when the temperature was decreased to 80 °C
(Table 1, entries 1, 19, 20).
Table 2. Arenediazonium salts with many valuable functional
groups present on aromatic ring such as ꢀOCH3, ꢀCl, –F, ꢀCH3,
and ꢀNO2 groups were screened and it was found that substrates
containing electron donating group deliver excellent products as
70 compared to substrates containing withdrawing groups (Table 2,
entries 2ꢀ10 ). The substituents at pꢀposition exhibit greater
reactivity than o- or mꢀposition. We also carried out the reaction
of disubstituted arenediazonium salts such as 3,5ꢀdimethoxy, 3,5ꢀ
dichloro, 3,4ꢀdichloro and 2,4ꢀdimethyl arenediazonium salts
75 with Sodium pꢀtoluenesulfinate and obtained excellent yield of
corresponding products (Table 2, entries 11ꢀ14). The substrate 4ꢀ
phenyl arenediazonium salt smoothly coupled giving 74% yield
of product (Table 2, entry 15).
Table 1. Otimization of reaction parameters.a
35
Entry Catalyst
Solvent Base Additive Temperature Yield
(°C)
100
100
100
100
100
100
(%)b
91
1
2
3
4
5
6
CuI
CuBr
Cu2O
DMSO K2CO3 TBAI
DMSO K2CO3 TBAI
DMSO K2CO3 TBAI
72
59
75
Cu(OAc)2 DMSO K2CO3 TBAI
CuSO4 DMSO K2CO3 TBAI
Cu(Phen) DMSO K2CO3 TBAI
(PPh3)2NO3
68
56c
80 Table 2. Reaction between sodium pꢀtoluenesulfinate and
7
Cu(acac)2 DMSO K2CO3 TBAI
100
67
arenediazonium salts.a
8
9
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
DMF K2CO3 TBAI
Toluene K2CO3 TBAI
100
100
100
100
100
100
100
100
100
100
100
120
80
26
20
Trace
56
74
69
Entry Arenediazonium Salts
1
Products
Yield (%)b
10
11
12
13
14
15
16
17
18
19
20
H2O
K2CO3 TBAI
DMSO NaHCO3 TBAI
DMSO Na2CO3 TBAI
DMSO K3PO4 TBAI
DMSO Cs2CO3 TBAI
DMSO tBuONa TBAI
91
89
88
47
2
3
Trace
Trace
10
82
92
DMSO K2CO3
DMSO K2CO3 TBAB
DMSO K2CO3 KI
KBr
O
O
S
DMSO K2CO3 TBAI
DMSO K2CO3 TBAI
Cl
83
2
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5
Conclusions
79
87
83
87
76
84
81
86
84
85
72
74
In summary, here we report the arylation of sulfones with
25 arenediazonium salts using homogeneous copper catalysed
system. Arenediazonium salts are the best alternatives to other
environmentally hazardous or costly arylating agents and are used
for the first time for arylation of sulfones. The methodology can
tolerate many important substituted arenediazonium salts giving
30 good to excellent yield of product.
6
7
Acknowledgements
The authors are thankful to the UGCꢀSAP, New Delhi, India for
the award of fellowship.
8
35 Notes and references
9
a Department of Chemistry, Institute of Chemical Technology, Matunga,
Mumbai – 400019, India. Fax: +91 22 33611020; Tel.: +91 22
33611111/2222; E-mail: jm.nagarkar@ictmumbai.edu.in
† Electronic Supplementary Information (ESI) available: [Experimental
40 procedures, Mass, 1H NMR and 13C NMR Spectra of synthesized
compound]. See DOI: 10.1039/b000000x/
10
11
12
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aReaction conditions: Sodium pꢀtoluenesulfinate (1 mmol),
Arenediazonium salts (1.3 mol), CuI (15 mol%), L1 (15 mol%),
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5
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20
The plausible reaction mechanism for arylation of sulfones is
illustrated in Fig.2.
Fig. 2 The Plausible mechanism for the arylation of sulfones.
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19. Synthesis of diaryl sulfones:
A mixture of sodium pꢀ
toluenesulfinate (1 mmol), arenediazonium salt (1.3 mmol),
copper iodide (15 mol%), N,N’ꢀdimethylethylenediamine (L1)
4
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1
Copper catalyzed synthesis of unsymmetrical diaryl sulfones from arenediazonium salt
and sodium p-toluenesulfinate
Sitaram Haribhau Gund, Radheshyam Suresh Shelkar, Jayashree Milind Nagarkar*
Department of Chemistry, Institute of Chemical Technology, Matunga, Mumbai – 400019,
India.
*Corresponding author. Tel.: +91 22 33611111/2222; fax: +91 22 33611020.
Email: jm.nagarkar@ictmumbai.edu.in
___________________________________________________________________________
Graphical abstract: