Copper-catalysed selective 3-sulfonylation of indoles: A mild synthesis of indolyl sulfones

Article abstract of DOI:10.3184/174751916X14733526548948

The selective C3-sulfonylation of some 4-, 5- and 6-substituted indoles using sodium arenesulfinates as reaction partners has been realised under mild conditions using catalytic CuI/1,10-phenanthroline at 70 °C. The reaction had a satisfactory application

Full text of DOI:10.3184/174751916X14733526548948

JOURNAL OF CHEMICAL RESEARCH 2016
VOL. 40 SEPTEMBER, 579–582
RESEARCH PAPER 579
Copper-catalysed selective 3-sulfonylation of indoles: a mild synthesis of
indolyl sulfones
Yi Du and Yunyun Liu*
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, P.R. China
The selective C3-sulfonylation of some 4-, 5- and 6-substituted indoles using sodium arenesulfinates as reaction partners has been
realised under mild conditions using catalytic CuI/1,10-phenanthroline at 70 °C. The reaction had a satisfactory application scope and
proceeded in fair to excellent yields.
Keywords: copper catalysis, indole, sulfinate, selective, C–H sulfonylation
Owing to their rich biological and medicinal profiles, indole
derivatives have attracted extensive research interest from the
chemical community and many related disciplines.1–3 Thus,
research on synthetic methods towards indole-based molecules
occupies a central position in modern organic synthesis.4–7
Among the numerous strategies for indole synthesis, the most
facile is the direct elaboration of indoles because of the high
and versatile reactivity of simple indoles.8–11 During recent
years, the synthesis of sulfur-containing indole derivatives
such as sulfenylated and sulfonylated indoles and other sulfur-
containing indole derivatives has received notable attention and
advances because of the inherent potential of these compounds
in the discovery of new lead compounds.12–18
differenttypesofproducts.Dependingonthecatalyticconditions
and reaction partners, the selective synthesis of various
sulfenylated or sulfonylated indoles by the functionalisation at
either the C-2 or C-3 position has been achieved. For example,
by employing sulfonohydrazides to react with indoles, Yang
and Tian observed the selective formation of 3-sulfenylated
indoles in the presence of molecular iodine (Eqn 1 in
Scheme 1).19 On the other hand, Tu and co-workers discovered
that the reactions of indoles with sulfonohydrazides provided
3-sulfonyl-2-diazosulfonylindoles in the oxidative system of
tetrabutylammonium iodide (TBAI)/tert-butyl hydroperoxide
(TBHP) (Eqn 2 in Scheme 1).20 In their investigation on the
sulfinate-based synthesis, Deng and co-workers found that the
reactions of sodium sulfinates and indoles yield sulfenylated
indoles when molecular iodine is employed as the catalyst.21
Interestingly, the reactions of identical starting materials have
been discovered to provide 2-sulfonylated products selectively
Among the reaction partners used for the C–S bond
elaboration of indoles, the sulfonic acid derivatives such as
sulfonohydrazides, sulfonyl chlorides and sulfinate salts have
been found to be highly efficient and versatile in providing
Yang and Tian:
C-3 sulfenylation of indoles
R3
S
I EtOH
/
2
R1
R3
NHNH2
R1
(1)
SO2
air
N
R2
N
R2
Tu and co-workers:
C-3 and C-2 difunctionalisation of indoles
R3
SO2
TBAI
R1
TBHP
R3
NHNH2
SO2
(2)
N
NSO2R3
R1
N
R2
MeCN
N
R2
Deng and co-workers:
C-2 sulfonylation of indoles
I
2/TBHP
AcOH
R1
R1
R3
R3
Na
SO2
(3)
(4)
SO2
N
N
R2
R2
This work:
C-3 sulfonylation of indoles
R2
SO2
CuI/DMSO
R1
R1
R2
SO2
Na
N
N
H
H
Scheme 1 Sulfenylation and sulfonylation of indole C–H bonds.
* Correspondent. E-mail: chemliuyunyun@jxnu.edu.cn

580 JOURNAL OF CHEMICAL RESEARCH 2016
when the modified reaction conditions of I2/TBHP in AcOH
are employed (Eqn 3 in Scheme 1).22 While elegant results on
the synthesis of these sulfenylated and sulfonylated indoles
have been achieved, selective synthetic approaches towards
3-sulfonylated indoles by corresponding C–H functionalisation
of indoles remain scarce.23–24 During our preparation of the
manuscript, Zhang and co-workers reported the copper-
catalysed C-3 sulfonylation of indoles employing sulfinates as
the sulfonyl source and closely related to our work.25 Based
on our longstanding interest in copper-catalysed coupling
chemistry, we report here our work on copper/iodide-catalysed
selective C-3 sulfonylation of indoles by using sulfinates as
reaction partners.
The entries respectively employing some different ligands and
bases suggested that 1,10-phen and K2CO3 were most favoured
in the reaction (Table 1, entries 8–14). In addition, the reactions
performed in different solvents proved that DMSO was the most
suitable medium (Table 1, entries 15–18). Finally, the variation
in the reaction temperature to 70 °C provided enhanced results
in terms of product yield (Table 1, entries 19–20).
Based on the optimised reaction conditions, we then
conducted an extended investigation on this approach by
synthesising different sulfonylated indoles. According to the
results (Table 2), the present synthetic method tolerated a variety
of different functional groups in both components, including
both electron-donating and electron-withdrawing groups. The
property of the substituent did not exhibit evident impact on the
reaction results. However, employing aliphatic sulfinates such
as sodium methanesulfinate turned out to be ineffective and in
addition, employment of N-substituted indoles was not possible.
No target products were observed in either of these reactions.
On the basis of the acceptable application scope, the potential
application of the reaction was further examined by performing
the model reaction at 10 times larger scale (using 3 mmol of
1a). It was found that a good yield (76%) of target product 3a
could be obtained (Eqn 5), demonstrating the present reaction
as a practical synthetic protocol.
To start the investigation, the model reaction of indole 1a
and sulfinate 2a was selected and the primary comparison
experiments conducted in the presence of CuBr and
1,10-phenanthroline
(1,10-phen)/K2CO3
showed
that
employment of excess sulfinate 2a was positive to the result
(Table 1, entries 1–2). The subsequent experiments employing
different copper catalysts disclosed the fact the CuI was the best
catalyst (Table 1, entries 3–6). Reducing the amount of CuI
load resulted in slight loss of product yield (Table 1, entry 7).
Table 1 Optimisation of reaction conditionsa
O
Na
SO2
O
Na
SO2
S
S
Standard
conditions
O
O
L
cat./
Cu
/base
(5)
solvent, T
N
N
N
H
DMSO (7 mL)
H
N
H
76
%
H
1a
2a
3a
3a
1a
2a
(6 mmol)
(3 mmol)
Entry
1
2c
3
4
5
6
7d
Catalyst
CuBr
CuBr
–
CuCl
CuI
CuBr2
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
Ligand (L)
Base
Solvent
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMF
Yieldb/%
60
46
Nr
52
83
53
74
52
Trace
43
Nr
36
Trace
34
Trace
Trace
Nr
45
85
L1
L1
L1
L1
L1
L1
L1
L2
L3
L4
–
L1
L1
L1
L1
L1
L1
L1
L1
L1
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
Cs2CO3
KOH
EtONa
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
Table 2 Scope for the selective C–H sulfonylation of indolesa
Na
SO2
R2
O
S
CuI,
1,10-phen
R1
O
R1
8
9
N
K2CO3 DMSO
,
H
70 oC
R2
2
N
H
3
10
11
12
13
14
15
16
17
18
19e
20f
1
Entry
1
2
3
4
5
6
7
R1
H
5-Br
6-Br
R2
CH3
CH3
CH3
CH3
CH3
CH3
CH3
H
Product
Yieldb/%
83
3a
3b
3c
3d
3e
3f
3g
3h
3i
75
80
69
58
66
68
60
82
5-OCH3
4-CHO
5-CN
5-COOCH3
H
Dioxane
Toluene
EtOH
DMSO
DSMO
8
9
65
5-Br
H
10
11
12
13
14
15
16
17
6-Br
5-CN
5-OCH3
H
5-Br
5-COOCH3
4-CHO
6-Br
H
H
H
OCH3
OCH3
NO2
NO2
Cl
3j
3k
3l
3m
3n
3o
3p
3q
74
58
67
87
76
74
66
59
P
N
N
N
N
N
NH2
L4
L1
L2
L3
aGeneral conditions: 1a (0.3 mmol), 2a (0.6 mmol), catalyst (20 mol%), ligand (20 mol%),
base (0.6 mmol), solvent (2 mL), stirred at 80 °C or reflux for 6 h.
bIsolated yield based on 1a. Nr = no reaction.
c2a (0.45 mmol).
aGeneral conditions: 1 (0.3 mmol), 2 (0.6 mmol), CuI (20 mol%), 1,10-phen (20 mol%),
K2CO3 (0.6 mmol), DMSO (2 mL), stirred at 70 °C for 6 h.
bIsolated yield based on 1.
dCuI in 15 mol% loading.
eReaction at 70 °C.
fReaction at 60 °C.

JOURNAL OF CHEMICAL RESEARCH 2016 581
Conclusion
(d, 1H, J = 8.0 Hz), 7.39 (d, 2H, J = 8.0 Hz), 2.33 (s, 3H); 13C NMR
(400 MHz, DMSO-d6): δ 143.5, 139.9, 138.1, 134.0, 129.8, 126.4, 126.0,
123.7, 122.8, 119.6, 116.2, 114.4, 104.2, 20.8; HRMS (ESI) calcd for
C16H13N2O2S+:[M + H]+: 297.0692; found: 297.0692.
In conclusion, by employing the strategy of copper(I) iodide
catalysis, we have developed an effective method for the
synthesis of indolyl-3-sulfones by selective C-3 sulfonylation.
The mild reaction conditions, short reaction time and high
efficiency in both conventional laboratory scale and gram scale
reactions have proved the usefulness of the present method in
the practical synthesis of these important indole derivatives.
Methyl 3-tosyl-1H-indole-5-carboxylate (3g): Yellow solid, m.p.
1
205–206 °C (lit. 25 198–200 °C); H NMR (400 MHz, DMSO-d6): δ
12.67 (s, 1H), 8.51 (s, 1H), 8.40 (s, 1H), 7.91–7.88 (m, 3H), 7.65 (d, 1H,
J = 8 Hz), 7.38 (d, 2H, J = 8.0 Hz), 3.91 (s, 3H), 2.32 (s, 3H); 13C NMR
(400 MHz, DMSO-d6): δ 166.5, 143.3, 140.3, 138.9, 133.5, 129.8, 126.1,
123.9, 123.2, 122.7, 120.7, 116.1, 113.0, 52.0, 20.8.
Experimental
All chemicals and solvents used in the experiments were obtained
from commercial sources and used directly without further treatment.
3-(Phenylsulfonyl)-1H-indole (3h): White solid; m.p. 143–144
1
°C (lit.26 149–150 °C); H NMR (400 MHz, DMSO-d6): δ 12.33 (s,
1H), 8.24 (d, 1H, J = 4.0 Hz), 8.00 (d, 2H, J = 4.0 Hz), 7.81 (d, 1H,
J = 4.0 Hz), 7.57–7.51 (m, 4H), 7.27–7.20 (m, 2H); 13C NMR (100 MHz,
DMSO-d6): δ 143.4, 136.3, 132.6, 131.6, 129.3, 126.1, 123.1, 123.0,
121.7, 118.5, 114.5, 112.8; HRMS (ESI) calcd for C14H12NO2S+: [M +
H]+: 258.0583; found: 258.0584.
1
All reactions were performed under an air atmosphere. The H NMR
and 13C NMR spectra were recorded on a Bruker Avance 400 MHz
instrument using CDCl3 or DMSO-d6 as solvent. The frequencies for
1H NMR and 13C NMR measurements were 400 MHz and 100 MHz,
respectively. The chemical shifts are reported in ppm using TMS as
internal standard. HRMS results were obtained on a micrOTOF-QII
Q-TOF mass spectrometer (ESI model).
5-Bromo-3-(phenylsulfonyl)-1H-indole (3i):27 White solid; m.p.
179–180 °C; 1H NMR (400 MHz, DMSO-d6): δ 12.50 (s, 1H), 8.29 (s,
1H), 8.00–7.97 (m, 2H), 7.92 (d, 2H, J = 8.0 Hz), 7.58–7.55 (m, 3H),
7.49 (d, 1H, J = 8.0 Hz); 13C NMR (100 MHz, DMSO): δ 143.64, 135.6,
133.5, 133.3, 129.9, 126.6, 126.4, 125.3, 121.1, 115.5, 115.0, 114.7.
6-Bromo-3-(phenylsulfonyl)-1H-indole (3j):27 Yellow solid; m.p.
Synthesis of sulfonylated indoles 3; general procedure
Indole 1 (0.3 mmol), sodium sulfinate 2 (0.6 mmol), CuI (0.06 mmol),
1,10-phenanthroline (0.06 mmol), K2CO3 (0.6 mmol) and DMSO
(2 mL) were added to a 25 mL round bottom flask equipped with
a condenser and stirring bar. The mixture was stirred at 70 °C for
6 h. Upon completion (TLC), the mixture was allowed to cool to
room temperature and water (10 mL) was added. The resulting
suspension was extracted with ethyl acetate (3 × 10 mL). The combined
organic phase was dried over Na2SO4. After filtration, the acquired
solution was collected and the solvent was removed under reduced
pressure at ca. 50 °C. The residue was subjected to silica gel column
chromatography to give pure products by using mixed petroleum ether
(60–90 °C) and ethyl acetate (v/v = 2:1) as eluent.
1
241–242 °C; H NMR (400 MHz, DMSO-d6): δ 12.42 (s, 1H), 8.26
(s, 1H), 8.01–7.99 (m, 2H), 7.77–7.73 (m, 2H), 7.62–7.57 (m, 3H),
7.39–7.36 (m, 1H); 13C NMR (400 MHz, DMSO-d6): δ 143.6, 137.5,
133.3, 133.1, 129.8, 126.6, 125.3, 122.6, 120.8, 116.4, 116.0, 115.5.
3-(Phenylsulfonyl)-1H-indole-5-carbonitrile (3k): White solid; m.p.
242–243 °C; 1H NMR (400 MHz, DMSO-d6): δ 12.77 (s, 1H), 8.43 (s,
1H), 8.24 (s, 1H), 8.05 (d, 2H, J = 8.0 Hz), 7.68 (d, 2H, J = 8.0 Hz),
7.63–7.55 (m, 4H); 13C NMR (400 MHz, DMSO-d6): δ 143.2, 138.7,
134.8, 133.5, 130.0, 126.9, 126.5, 124.2, 123.3, 120.1, 116.3, 114.9,
104.8; HRMS (ESI) calcd for C15H11N2O2S+: [M + H]+: 283.0536;
found: 283.0538.
3-Tosyl-1H-indole (3a):26 Yellow solid; m.p. 165–166 °C; H NMR
1
5-Methoxy-3-(phenylsulfonyl)-1H-indole (3l): Black solid; m.p.
152–153 °C (lit.28 91 °C, there are no other literature values); 1H NMR
(400 MHz, CDCl3): δ 9.35 (s, 1H), 7.98 (d, 2H, J = 4.0 Hz), 7.78 (d,
1H), 7.49–7.44 (m, 3H), 7.31 (s, 1H), 7.26 (t, 1H, 8.0 Hz), 6.87 (d, 1H,
J = 8.0 Hz), 3.81 (s, 3H); 13C NMR (400 MHz, CDCl3): δ 155.5, 142.6,
132.1, 130.6, 129.7, 128.5, 126.0, 123.7, 113.9, 112.6, 100.2, 55.3.
3-[(4-Methoxyphenyl)sulfonyl]-1H-indole (3m): Brown solid;
m.p. 144–145 °C (lit.26 157–159 °C); 1H NMR (400 MHz, DMSO-d6):
δ 12.23 (s, 1H), 8.15 (s, 1H), 7.91 (d, 2H, J = 8.0 Hz), 7.77 (d, 1H,
J = 8.0 Hz), 7.50 (d, 1H, J = 8.0 Hz), 7.24–7.19 (m, 2H), 7.06 (d, 2H,
J = 8.0 Hz), 3.78 (s, 3H); 13C NMR (400 MHz, DMSO-d6): δ 162.8,
136.8, 135.5, 131.4, 128.9, 123.5, 123.4, 122.1, 119.0, 115.9, 114.9, 113.2,
56.0.
(400 MHz, CDCl3): δ 9.62 (s, 1H), 7.89 (d, 3 H, J = 7.6 Hz), 7.82 (s,
1 H), 7.38–7.37 (m, 1H), 7.22 (t, 4H, J = 6.8 Hz), 2.34 (s, 3H);13C NMR
(100 MHz, CDCl3): δ 143.4, 140.3, 136.4, 130.0, 129.6, 126.6, 123.8,
123.4, 122.3, 119.2, 116.6, 112.3, 21.3; HRMS (ESI) calcd for
C15H14NO2S+:[M + H]+: 272.0740; found: 272.0743.
5-Bromo-3-tosyl-1H-indole (3b): Brown solid; m.p. 205–206
°C (lit.25 193–196 °C); 1H NMR (400 MHz, DMSO-d6): δ 12.46
(s, 1H), 8.26 (s, 1H), 7.90 (s, 1H), 7.86 (d, 2 H, J = 8.0 Hz), 7.49 (d,
2H, J = 8.0 Hz), 7.38–7.32 (m, 3H), 2.28 (s, 3H); 13C NMR (100
MHz, DMSO-d6): δ 143.2, 140.3, 135.1, 132.7, 129.8, 126.2, 125.8,
124.8, 120.6, 114.9, 114.7, 114.4, 20.8; HRMS (ESI) calcd for
C15H1379BrNO2S+:[M + H]+: 394.9845; found: 349.9844.
6-Bromo-3-tosyl-1H-indole (3c): Yellow solid; m.p. 202–203 °C;
1H NMR (400 MHz, DMSO-d6): δ 12.39 (s, 1H), 8.24 (s, 1H), 7.88 (d,
2H, J = 8.0 Hz), 7.75 (d, 2H, J = 8.0 Hz), 7.36 (t, 3H, J = 8.0 Hz), 2.31
(s, 3H); 13C NMR (100 MHz, DMSO-d6): δ 143.7, 140.8, 137.7, 132.7,
130.2, 126.7, 125.2, 122.6, 120.8, 116.3, 115.9, 21.3; HRMS (ESI) calcd
for C15H1379BrNO2S+:[M + H]+: 394.9845; found: 349.9846.
5-Methoxy-3-tosyl-1H-indole (3d):24 Black solid; m.p. 104–105 °C;
1H NMR (400 MHz, CDCl3): δ 9.19 (s, 1H), 7.87 (d, 2H, J = 8.0 Hz),
7.77 (s, 1H), 7.31–7.23 (m, 4H), 6.87 (d, 1H, J = 8.0 Hz), 3.82 (s, 3H),
2.35 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 155.9, 143.4, 140.3, 131.2
130.0, 129.6, 126.5, 124.2, 114.2, 113.1, 100.8, 55.7, 21.4.
5-Bromo-3-[(4-methoxyphenyl)sulfonyl]-1H-indole (3n): Yellow
1
solid; m.p. 212–213 °C; H NMR (400 MHz, DMSO-d6): δ 12.45 (s,
1H), 8.23 (s, 1H), 7.91 (d, 3H, J = 8.0 Hz), 7.49 (d, 1H, J = 8.0 Hz), 7.37
(d, 1H, J = 8.0 Hz), 7.06 (d, 2H, J = 8.0 Hz), 3.76 (s, 3H); 13C NMR
(400 MHz, DMSO-d6): δ 162.4, 135.1, 134.7, 132.4, 128.4, 125.8,
124.6, 120.5, 115.1, 114.9, 114.5, 114.3, 55.5; HRMS (ESI) calcd for
C15H1379BrNO3S+:[M + H]+: 365.9794; found: 365.9785.
Methyl 3-[(4-nitrophenyl)sulfonyl]-1H-indole-5-carboxylate (3o);
1
Yellow solid; m.p. 248–249 °C; H NMR (400 MHz, DMSO-d6): δ
12.90 (s, 1H), 8.56 (s, 1H), 8.52 (s, 1H), 8.41 (d, 2H, J = 8.0 Hz), 8.26
(d, 2H, J = 8.0 Hz), 7.93 (d, 1H, J = 8.0 Hz), 7.69 (d, 1H, J = 8.0 Hz),
3.92 (s, 3H); 13C NMR (400 MHz, DMSO-d6): δ 166.4, 149.7, 148.2,
139.0, 135.0, 127.6, 124.8, 124.2, 123.6, 122.8, 120.4, 114.0, 113.3,
52.0; HRMS (ESI) calcd for C16H13N2O6S+:[M + H]+: 361.0489; found:
361.0483.
3-Tosyl-1H-indole-4-carbaldehyde (3e). White solid; m.p.
1
203–204 °C; H NMR (400 MHz, DMSO-d6): δ 12.90 (s, 1H), 10.74
(s, 1H), 8.54 (s, 1H), 7.92 (d, 1H, J = 8.0 Hz), 7.74 (t, 3H, J = 8.0 Hz),
7.46–7.38 (m, 3H), 2.34 (s, 1H); 13C NMR (100 MHz, DMSO-d6):
δ 192.0, 143.5, 139.4, 138.6, 136.9, 129.9, 127.5, 126.2, 123.1, 121.9,
121.3, 119.3, 114.4, 20.8; HRMS (ESI) calcd for C16H14NO3S+: [M +
H]+: 300.0689; found: 300.0688.
3-[(4-Nitrophenyl)sulfonyl]-1H-indole-4-carbaldehyde
(3p):
1
White solid; m.p. 234–235 °C; H NMR (400 MHz, DMSO-d6): δ
13.1 (s, 1H), 10.6 (s, 1H), 8.7 (s, 1H), 8.40 (d, 2H, J = 8.0 Hz), 8.16
(d, 2H, J = 8.0 Hz), 7.96 (d, 1H, J = 8.0 Hz), 7.77 (d, 1H, J = 8.0 Hz),
7.49 (t, 1H, J = 8.0 Hz); 3C NMR (400 MHz, DMSO-d6): δ 191.4, 149.7,
147.9, 138.7, 138.2, 127.7, 127.7, 124.8, 123.4, 122.7, 121.5, 119.5, 112.5;
3-Tosyl-1H-indole-5-carbonitrile (3f):Brown solid; m.p. 166–167 °C
1
(lit.25 183–185 °C); H NMR (400 MHz, DMSO-d6): δ 12.80 (s, 1H),
8.44 (s, 1H), 8.27 (s, 1H), 7.97 (d, 2H, J = 8.0 Hz), 7.72 (d, 1H), 7.65

582 JOURNAL OF CHEMICAL RESEARCH 2016
HRMS (ESI) calcd for C15H11N2O5S+: [M + H]+: 331.0383; found:
331.0395.
8
9
A. Suárez, M. Gohain, M.A. Fernández-Rodríguez and R. Sanz, J. Org.
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6-Bromo-3-[(4-chlorophenyl)sulfonyl]-1H-indole (3q): Yellow
liquid; 1H NMR (400 MHz, DMSO-d6): δ 12.46 (s, 1H), 8.26 (s, 1H),
7.98 (d, 2H, J = 8.0 Hz), 7.72 (t, 2H), 7.64 (d, 2H, J = 8.0 Hz), 7.38–7.36
(m, 1H); 13C NMR (400 MHz, DMSO-d6): δ 142.4, 138.3, 137.7, 133.4,
130.0, 128.6, 125.6, 122.5, 120.7, 116.4, 116.0, 114.8; HRMS (ESI)
calcd for C14H1079Br35ClNO2S+:[M + H]+: 369.9299; found: 369.9349.
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Financial support from the National Natural Science Foundation
of China (21562024) and the Natural Science Foundation
of Jiangxi Province (20142BAB213007) is gratefully
acknowledged.
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Electronic Supplementary Information
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stl.publisher.ingentaconnect.com/content/stl/jcr/supp-data
Received 25 April 2016; accepted 5 August 2016
Paper 1604069 doi: 10.3184/174751916X14733526548948
Published online: 23 September 2016
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