Simple and efficient copper-catalyzed S-arylation of diaryl disulfides with triarylbismuthanes under aerobic conditions

Article abstract of DOI:10.1016/j.tetlet.2011.09.071

Novel and simple copper-catalyzed C(aryl)-S bond formation of diaryl disulfides with bismuth reagents is described. Reactions of diaryl disulfides with triarylbismuthanes in the presence of CuOAc (10 mol %) and 1,10-phenanthroline (10 mol %) under aerobic conditions led to the formation of unsymmetrical diaryl sulfides in satisfactory yields. The reaction is atom-economic and all three aryl groups of the triarylbismuthanes and both sulfanyl groups of the diaryl disulfides could be transferred to the coupling products.

Full text of DOI:10.1016/j.tetlet.2011.09.071

Tetrahedron Letters 52 (2011) 6403–6406
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Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
Simple and efficient copper-catalyzed S-arylation of diaryl disulfides
with triarylbismuthanes under aerobic conditions
a,b
a
a
a,
⇑
Shuji Yasuike , Motokazu Nishioka , Naoki Kakusawa , Jyoji Kurita
a
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan
Organization for Frontier Research in Preventive Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan
b
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 28 July 2011
Revised 12 September 2011
Accepted 15 September 2011
Available online 21 September 2011
Novel and simple copper-catalyzed C(aryl)–S bond formation of diaryl disulfides with bismuth reagents is
described. Reactions of diaryl disulfides with triarylbismuthanes in the presence of CuOAc (10 mol %) and
1,10-phenanthroline (10 mol %) under aerobic conditions led to the formation of unsymmetrical diaryl
sulfides in satisfactory yields. The reaction is atom-economic and all three aryl groups of the triaryl-
bismuthanes and both sulfanyl groups of the diaryl disulfides could be transferred to the coupling products.
Ó 2011 Elsevier Ltd. All rights reserved.
Keywords:
Cross-coupling
S-Arylation
Bismuthane
Disulfide
Copper catalyst
Transition-metal-catalyzed carbon–sulfur bond formation by
cross-coupling reaction has attracted increasing attention in the
last two decades due to its wide applicability in biological, phar-
maceutical, and material sciences.1 In these reactions, a wide
variety of transition metals, such as Pd, Ni, Cu, Fe, Rh, Ru, Co, Zr,
3
organobismuth compounds, such as triarylbismuthanes (Ar Bi),
can also be used as arylating agents in copper-mediated N- and O-
arylations, although stoichiometric amounts of Cu reagents have
,2
14,15
been used.
However, to the best of our knowledge, transition
metal-catalyzed C(aryl)–S bond formation using organobismuth
compounds has not hitherto been reported. Herein, we report a no-
vel and useful copper-catalyzed S-arylation of diaryl disulfides with
triarylbismuthanes under aerobic conditions.
3
Pt, Au, and In have been employed as effective catalysts. On the
other hand, copper-catalyzed carbon–heteroatom bond formation
4
by this protocol is a powerful tool in organic synthesis. However,
the formation of C–S bonds leading to diaryl sulfides has been less
studied than the corresponding C–N and C–O bond formations. As
for copper-catalyzed S-arylation, the reactions are mainly con-
ducted by reacting the following classes of compounds: (1) aryl
We initially focused our attention on the determination of the
optimum conditions for the S-arylation of di-p-tolyl disulfide (4a)
with organobismuth(III) and (V) compounds, such as Ph
3
Bi (1a),
Ph BiCl (2), and Ph Bi(OAc) (3). The results, including those per-
3
2
3
2
5
6
halides with thiols or disulfides, (2) arylboronic acids with
taining to the search for suitable ligands, catalysts, and active bis-
muth reagents for the reaction, are summarized in Table 1. To
search for the optimal ligand, we first examined the reaction of 4a
(0.75 mmol) with 1a (0.5 mmol) using CuI (0.05 mmol) as catalyst
and various ligands (L1–L6) under aerobic conditions in DMSO at
100 °C (entries 1–7). These results showed that 1,10-phenanthroline
(L2) was the best ligand for the reaction in terms of the yield of the
expected sulfide 5 and the reaction time. It should be noted that all
three phenyl groups on bismuth and both sulfanyl groups of the
disulfide participated in this reaction. The addition of the ligand
was important, which was probed by carrying out the reaction of
4a and 1a in its absence (entry 1). Screening of prominent catalysts
showed that all copper(I) and (II) catalysts examined here were
effective (entries 3 and 8–13). Among these, CuOAc appeared to be
the best catalyst for this reaction in terms of the yield (90%) of
S-arylation product 5. It has been reported that pentavalent
thiols, disulfides, or N-thioimides,9 or (3) arylsilanes with
7
8
1
0
disulfides. In these reactions, the use of disulfides as sulfanyl
precursors is advantageous because they have less unpleasant
odors and are more stable in air than thiol derivatives.
Organobismuth compounds are normally non-toxic, environ-
mentally benign, and potentially useful candidates as synthetic
1
1
reagents. For instance, they have been reported to be useful for a
variety of transition metal-catalyzed cross-coupling reactions.
Pentavalent organobismuth compounds, such as triarylbismuth
diacetates [Ar
Cu-catalyzed C(aryl)–N and –O bond formations.
3 2
Bi(OAc) ], have proved to be effective agents for
12,13
Trivalent
⇑
Corresponding author. Tel.: +81 76 229 1165; fax: +81 76 229 2781.
E-mail address: j-kurita@hokuriku-u.ac.jp (J. Kurita).
0
040-4039/$ - see front matter Ó 2011 Elsevier Ltd. All rights reserved.
doi:10.1016/j.tetlet.2011.09.071

6
404
S. Yasuike et al. / Tetrahedron Letters 52 (2011) 6403–6406
triphenylbismuth dichloride (2) and diacetate (3) are effective
ArSAr'
F
ArSAr'
agents in carbon-heteroatom bond formation, such as N- and
F
1
2,13
N
N
(III) SAr'
N
N
(III) SAr'
O-arylations,
however, these bismuth(V) compounds were less
N
N
X
X
N
N
Cu
Cu
Cu
Cu
Ar
Ar
active in the present S-arylation (entries14 and 15). Screening of sol-
vents showed that the reaction proceeded effectively in DMSO
(I)
(I)
X
X
E
A
E
(
90%), DMF (82%), and NMP (59%), whereas CH
3
CN, 1,4-dioxane, tol-
Cycle A
Cycle B
(Ar'S)2
uene, and 1,2-DCE gave inferior results. It should be noted that the
reaction of 4a and 1a under an argon atmosphere gave 5 in low yield
Bi O
2 3
H O
2
+
Ar Bi
(
Ar'S)2
3
O
2
(
24 h: 18%), implying the participation of aerobic oxygen and/or
+
O
moisture in facilitating the reaction. However, the yield of 5 did
not improve, even when the reaction was carried out under an oxy-
gen atmosphere (24 h: 75%). This result also suggests a contribution
of water to the reaction, although the reaction of 1a and 4a in DMSO/
2
Ar Bi
3
H
O
N
N
Ar
X
N
N
SAr'
X
N
N
N
N
Cu
Cu
Cu
Cu
X2
(II)
(II)
O
(II)
(II)
H
H
7
2
O (10:1) gave 5 in low yield after a longer reaction time (24 h,
9%). Consequently, the best result was obtained when 1a was
treated with 4a using CuOAc and 1,10-phenanthroline in DMSO at
Bi O
O + H O
2 2
C
2
3
B
D
Figure 1. Possible mechanisms for S-arylation of diaryl disulfides with
1
00 °C in air.
triarylbismuthanes.
In order to demonstrate the efficiency and generality of this
protocol, we examined the reactions of various triarylbis
I
the generation of bimetallic intermediate [(phen)Cu X]
2
A from
muthanes 1b–i and diaryl disulfides 4b–l, and the results are
summarized in Table 2.16 Reactions of triarylbismuthanes 1b–i
CuOAc or CuI and 1,10-phenanthroline. Molecular oxygen and
moisture in air and/or the solvent would bind to intermediate A,
which is thereby oxidized to produce the catalytically active
(l-hydroxide)copper(II) complex B. In cycle A, transmetallation
between triarylbismuthane and B forms the intermediate C, and
with diphenyl disulfide (4b) gave the corresponding diaryl sul-
fides 5–11 in good yields (67–87%), except for the 2-thienyl deriv-
ative 12 (31%) (entry 8). These S-arylations are sensitive to the
electronic nature of the aryl groups on bismuth, such that the
reactions of the bismuthanes bearing electron-withdrawing
groups, 1e and 1f, proceed more rapidly than those of bismu-
thanes bearing electron-donating groups, 1b and 1c. Sterically
hindered ortho-substituted bismuth compounds 1g and 1h could
also be coupled with 4b to afford the corresponding sulfides
without any difficulty (entries 6 and 7).
Next, various diaryl disulfides 4c–l were reacted with
triphenylbismuthane 1a under the same reaction conditions (en-
tries 9–18). Disulfides 4c–f with electron-donating and -withdraw-
ing groups on the aromatic rings gave the corresponding coupling
products in satisfactory yields (entries 9–12). In contrast to the
above reactions shown in entries 1, 2, 4, and 5, in which S-aryl
ations by triarylbismuthanes bearing electron-deficient aryl groups
proceeded more rapidly than those by triarylbismuthanes bearing
electron-rich aryl groups, the reactions of diaryl disulfides with
bismuthanes bearing electron-deficient aryl groups proceeded
more slowly than those with bismuthanes bearing electron-rich
aryl groups (entries 9–12). From the viewpoint of steric demand
in the present S-arylation, the combination of sterically hindered
bismuth reagent and less hindered disulfides would be superior
to the opposite combination of less hindered bismuth reagent
and hindered disulfides for the preparation of sterically bulky
diaryl sulfides (entries 7 and 14). Additionally, reactions of the het-
erocyclic disulfides 4i–k gave the corresponding aryl sulfides 12,
1
8
subsequent oxidative addition of an aryl sulfide moiety of the
0
0
disulfide (Ar –S–S–Ar ) to C affords the Cu(III) intermediate E. Suc-
cessive reductive elimination of the coupling product F from the
intermediate E regenerates the bimetallic intermediate A. Another
catalytic cycle B might be possible, in which a ligand-exchange
reaction of B with the arylsulfanyl moiety of diaryl disulfide to
form D occurs in advance of oxidative addition of an aryl group
of the bismuth reagent to the Cu(II) species D.
Table 1
a
S-Arylation of di-p-tolyl disulfide with triphenylbismuthane
Cu cat. (10 mol%)
Ph
Ligand (10 mol%)
S
Ph Bi
+
(p-TolS)2
Ph
p-Tol
Ph
DMSO, in Air
5
1a
4a
X
Ph Bi
X
Ph
Ph
Me N
NMe2
2
N
N
L1
N
N
L2
L3
2: X = Cl
: X = OAc
MeHN
NHMe
L-proline
PPh3
3
L4
L5
L6
Entry
Bi reag.
Cu cat.
Ligand
Time (h)
Yieldb (%)
1
4, and 15 (entries 15–17). It is noteworthy that, under the present
1
2
3
4
5
6
7
8
9
10
1a
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuCl
CuBr
Cu(OAc)
CuCl
CuBr
Cu(OAc)
Cu(OAc)
Cu(OAc)
—
24
6
3
27
78
78
59
43
38
36
76
reaction conditions, the reaction of bis(4-acetamidophenyl) disul-
fide 4l with 1a afforded S-arylated product 16 as the sole isolated
product, with the N–H bond of the acetamido moiety of 4l remain-
ing intact (entry 18), even though triphenylbismuthane has been
reported to be effective for Cu-mediated C(aryl)–N bond formation
L1
L2
L3
L4
L5
L6
L2
L2
L2
L2
L2
L2
L2
L2
24
24
24
24
24
24
6
24
24
6
1
4b,f,g
in amide derivatives.
The reaction mechanism of the present S-arylation with tri
arylbismuthane 1 is unclear at present. We consider that similar
mechanisms for the N-arylation with arylboronic acids proposed
87
90 (87)c
74
11
2
1
7
12
2
81
73
39
38
by Collman, and reactions with pentavalent bismuth compounds
1
1
3
4
2
1
4a
proposed by Barton,
as well as for the S-arylation with arylbo-
2
3
24
24
8a,b
ronic acids as proposed by Taniguchi
and with arylsilanes as
15
1
0
proposed by Luo, may be relevant to the S-arylation demon-
strated here. Possible mechanisms of the reaction between tri
arylbismuthanes and disulfides in the formation of diaryl sulfides
are depicted in Figure 1. The first step of the reaction would be
a
Reaction conditions: 1a, 2, or 3 (0.5 mmol), 4a (0.75 mmol), Cu cat. (0.05 mmol),
and ligand (0.05 mmol) in DMSO (5 mL) at 100 °C in air.
b
GC yield. The yield 100% corresponds to the formation of 1.5 mmol of 3.
c
Isolated yield.

S. Yasuike et al. / Tetrahedron Letters 52 (2011) 6403–6406
6405
Table 2
a
Copper-catalyzed S-arylation of diaryl disulfides with triarylbismuthanes
Cu(OAc) (10 mol%)
Ar
1
,10-phenanthroline (10 mol%)
DMSO, 100 oC, Air
S
Ar Bi
+
3 / 2 Ar'S SAr'
3
Ar
Ar'
Ar
5
-16
1
4
0
0
Timeb (h)
Yieldc (%)
Entry
Ar
3
Bi
Ar
(Ar S)
2
Ar
Product
1
2
3
4
5
1b
1c
1d
1e
1f
4-Methoxyphenyl
4b
Phenyl
8
6
6
3
3
S
S
S
S
S
OMe
6: 83
5: 87
7: 81
8: 67
9: 83
4-Methylphenyl
Me
4-Chlorophenyl
Cl
4-Ethoxycarbonylphenyl
4-Trifluoromethylphenyl
COOEt
CF
3
Me
6
7
1g
2-Methylphenyl
Mesityl
6
10: 84
S
Me
1h
1i
2
2
S
Me
11: 70
12: 31
Me
S
8
9
2-Thienyl
Phenyl
S
1a
1a
1a
1a
4c
4d
4e
4f
4-Methoxyphenyl
4-Chlorophenyl
3
S
S
S
S
OMe
Cl
6: 84
7: 88
9: 87
13: 81
1
1
1
0
1
2
7
4-Trifluoromethylphenyl
4-Nitrophenyl
6
CF
3
24
NO
2
Me
1
1
3
4
1a
1a
4g
4h
2-Methylphenyl
Mesityl
6
2
10: 83
11: 55
S
Me
S
Me
Me
S
1
1
5
6
1a
1a
4i
4j
2-Thienyl
6
12: 86
14: 73
S
N
2-Benzothiazolyl
24
S
S
S
S
1
1
7
8
1a
1a
4k
4l
2-Pyridinyl
24
3
15: 51
16: 75
N
4-Acetamidophenyl
NHCOCH
3
a
b
c
Reaction conditions: 1 (0.5 mmol), 4 (0.75 mmol), CuOAc (0.05 mmol), and 1,10-phenanthroline (0.05 mmol) in DMSO (5 mL) at 100 °C in air.
Heated until the spot of bismuth reagent was disappeared on TLC.
Isolated yield.
In conclusion, we have developed a novel, synthetically useful,
References and notes
atom-economic, and experimentally simple copper-catalyzed S-
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of the disulfide could be involved in this reaction. The reaction gave
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even with diaryl disulfides and triarylbismuthanes bearing elec-
tron-donating and -withdrawing functional groups. Studies on
the reaction mechanisms of the present S-arylation and reactions
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16. Typical procedure: A mixture of triphenylbismuthane 1a (0.5 mmol), di-p-tolyl
disulfide 4a (0.75 mmol), CuOAc (0.05 mmol), and 1,10-phenanthroline (L2;
0.05 mmol) in DMSO (5 mL) was heated at 100 °C for 6 h in air. After dilution of
7
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2
the reaction mixture with CH
separated and the aqueous layer was extracted with CH
combined organic layers were washed with 5% aqueous ammonia and water,
dried over anhydrous MgSO , and concentrated under reduced pressure. The
2
Cl
2
(50 mL) and water (30 mL), the phases were
9
.
2
Cl
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(30 ꢀ 2 mL). The
1
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