Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes

Article abstract of DOI:10.1016/j.tetlet.2018.09.065

A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distannanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demonstrates the potential applications of this method in organic synthesis.

Full text of DOI:10.1016/j.tetlet.2018.09.065

Tetrahedron Letters xxx (2018) xxx–xxx
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Tetrahedron Letters
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Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling
reaction of sodium arylsulfinates with distannanes
Chang Lian a, Guanglu Yue a, Haonan Zhang a, Liyan Wei a, Danyang Liu a, Sichen Liu a, Huayi Fang b,
Di Qiu a,
⇑
a College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-organic Hybrid Functional Material
Chemistry, Ministry of Education, Tianjin Normal University, Tianjin 300387, China
b Department of Chemistry, Fudan University, Shanghai 200433, China
a r t i c l e i n f o
a b s t r a c t
Article history:
A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distan-
nanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent
yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demon-
strates the potential applications of this method in organic synthesis.
Received 12 August 2018
Revised 19 September 2018
Accepted 25 September 2018
Available online xxxx
Ó 2018 Elsevier Ltd. All rights reserved.
Keywords:
Palladium catalysis
Desulfitative
Cross-coupling
Sodium arylsulfinates
Arylstannane
Introduction
ArOTf with distannanes has been developed (Scheme 1c) [9].
Moreover, the radical type stannylation of aryl diazonium salts or
Organotin reagents, especially for arylstannanes derivatives,
have been found great applications in organic synthesis and other
fields [1]. In particular, the Stille coupling reaction, in which the
essence is the cross-coupling reaction with organotin reagents, is
rapidly becoming a powerful synthetic strategy for selective CAC
bond formation [2]. Particularly, compared with Suzuki-Miyaura
reactions, the Stille coupling methodology has been found to be
highly effective for synthesizing functional materials [1j].
Moreover, aryl C-Sn bond can further be applied in functional
group transformations, including CAN [3], CAF [4], CAOCF3 [5],
and C–B bond [6] formation. The wide application has created con-
siderable need for the easy access to aryl stannane derivatives.
However, the synthetic methods for accessing arylstannane com-
pounds are still limited. The most commonly used strategy to syn-
thesize functionalized aryl stannanes is the reaction of trialkyl tin
halide with aromatic metal reagents, including aryl magnesium,
-lithium, or -zinc reagents (Scheme 1a) [7]. Alternative methods
are the aromatic nucleophilic substitution between aryl halides
or ammonium salts and trialkyl stannyl anion (Scheme 1b) [8]. In
addition, Pd-catalyzed cross-coupling reaction from aryl halides/
aryl iodides are carried out under transition-metal-free condition
(Scheme 1d) [10]. Recently, the Ni-catalyzed stannylation reactions
of aryl esters were developed by Martín [11a] and Rueping [11b],
using silylstannyl derivatives and distannanes as the stannylation
reagents respectively (Scheme 1e).
Arylsulfinic acids or their arylsulfinate salts, which can be con-
veniently synthesized from the corresponding aryl sulfonyl
halides, have played important role as versatile intermediates in
organic synthesis because of their readily availability, air stability
and low price [12]. In addition to participating in sulfonylation
reactions [13], arylsulfinic acids or sodium arylsulfinates can be
served as novel alternatives for transition-metal-catalyzed desulfi-
tative CAC bond formations by releasing SO2 [14]. As a new strat-
egy of aryl sources, the importance of desulfitative coupling
reactions has been adequately proved in Heck-type reactions
[15], synthesis of biaryls [16], synthesis of aryl ketones [17] and
CAH bond arylation [18]. However, desulfitative coupling reaction
of arylsulfinates for constructing carbon-heteroatom bond still
remains great challenge. Recently, Wang and Xiao have reported
the novel Pd-catalyzed desulfitative CAP coupling of sodium aryl-
sulfinates respectively [19a,b]. The Cu-promoted desulfitative N-
arylation with sodium arylsulfinates was also explored [19c].
Based on our interests in desulfitative coupling reactions and the
⇑
Corresponding author.
E-mail address: qiudi@pku.edu.cn (D. Qiu).
https://doi.org/10.1016/j.tetlet.2018.09.065
0040-4039/Ó 2018 Elsevier Ltd. All rights reserved.
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2
C. Lian et al. / Tetrahedron Letters xxx (2018) xxx–xxx
Table 1
Optimization of reaction conditions.a
,
A
[Pd]
g2CO3
+
Na
SO2
Bu )
SnBu3
(Sn
3
2
solvent, temp.
1a
2a
3a
Entry
Solvent
T (°C)
[Pd] (mol%)
Yield (%)b
1
2
3
4
5
6
7
8
DMF
DMF
DMF
DMF
DMF
DMF
DMF
DMA
Toluene
Dioxane
DMA
DMA
DMA
60
80
Pd(PPh3)2Cl2(5)
Pd(PPh3)2Cl2(5)
Pd(PPh3)2Cl2(5)
PdCl2(dppp) (5)
Pd(acac)2 (5)
Pd(PtBu3)2(5)
Pd(PtBu3)2(5)
Pd(PtBu3)2(5)
Pd(PtBu3)2(5)
Pd(PtBu3)2(5)
Pd(PtBu3)2(5)
Pd(PtBu3)2(3)
Pd(PtBu3)2(3)
Pd(PtBu3)2(3)
Pd(PtBu3)2(3)
/
trace
20
44
Trace
20
64
71
73
61
35
93
97
83
63
trace
34
110
110
110
110
120
120
120
120
140
140
140
140
140
140
9
10
11
12
13c
14d
15e
16
DMA
DMA
DMA
a
Reaction conditions: sodium benzenesulfinate 1a (0.3 mmol, 1.5 equiv), hex-
abutyldistannane 2a (0.2 mmol, 1.0 equiv), Ag2CO3 (0.3 mmol, 1.5 equiv), Pd
catalysis (3–5 mol%), solvent (2 mL), 1 h.
b
Isolated yields.
Ag2CO3 (0.24 mmol, 1.2 equiv).
Sodium aryl sulfinate (0.24 mmol, 1.2 equiv).
Without Ag2CO3. DMA = N,N-dimethylacetamide.
c
d
e
Scheme 1. Synthetic methods for arylstannanes.
importance of aryl stannane reagents, herein we report the desul-
fitative cross-coupling reaction of sodium aryl sulfinates with hex-
abutyldistannane under palladium catalysis (Scheme 1f).
group tolerance to both electron-donating and electron-withdraw-
ing substituents on the aromatic rings, such as alkyl (3b, 3c), halo-
gen (3d, 3e, 3f), vinyl (3g), cyano (3h), trifluoromethyl (3i),
ethoxycarbonyl (3j), acetyl (3k) and trifluoromethoxy (3l), aceta-
mino (3m), and azo groups (3n). In the cases of 3f and 3g, the
low yields are due to the Pd-catalyzed stannylation of C–Br bond
to generate bis-stannylated benzene derivative, or Heck reaction
with vinyl moiety respectively. In addition to the para-substituted
arylstannanes, meta- and ortho-substituted (3o–3t) and multi-sub-
stituted aryl stannane compounds (3u, 3v) could also be got in
moderate to good yields. Furthermore, naphthyl derivatives (3w,
3x) and heterocyclic arylsulfinates (3y, 3z, 3aa) also showed good
compatibility under the standard condition. The low yield in the
case of 3y is attributed to the instability on silica gel column chro-
matography. Moreover, other hexaalkyl distannanes (2b, 2c) were
also subjected to this coupling reaction, affording corresponding
trialkyl arylstannanes (3ba, 3ca) with moderate yields.
To manifest the practical application of this method, the stanny-
lation reaction has been carried out on a gram scale for five arylsul-
finates. As shown in Scheme 3, the corresponding arylstannanes
products (3a, 3b, 3h, 3l, 3q) were successfully obtained with com-
parable good yields.
Since purification of aryl stannane compounds is tedious and
some aryl stannanes are not stable on the silica gel column chro-
matography, we continuously perform the consecutive Pd-cat-
alyzed Stille cross-coupling reaction without the purification of
crude stannylation products. The desulfitative stannylation and
Pd-catalyzed Stille reaction is carried out in a tandem manner.
After the accomplishment of the stannylation, the reaction system
was filtered to remove the insoluble precipitates, followed by
removing the DMA solvent under reduced pressure. Subsequently,
the crude arylstannanes was then subjected to the Stille reaction to
afford the diaryl products in high yields (Scheme 4).
Results and discussion
At the outset, we started our investigation by examining Pd
(PPh3)2Cl2 catalyzed cross-coupling reaction of sodium benzene-
sulfinate 1a with hexabutyldistannane 2a in the presence of Ag2-
CO3 in DMF at 60 °C. To our disappointment, only a trace amount
of product 3a could be detected (entry 1). Subsequently, the reac-
tion temperature was raised and the yield improved to 44% (entry
2, 3). Various palladium catalysts were examined at 110 °C, and Pd
(PtBu3)2 was found as the best catalyst in this reaction (entry 3–6).
Then we continued to heat up and tried different solvents by using
Pd(PtBu3)2 as the catalyst at 120 °C, and we observed that a satis-
factory yield could be obtained by using the high boiling point sol-
vent N,N-dimethylacetamide (DMA) (entry 7–10). Considering that
high temperature was favorable for this desulfitative cross-cou-
pling reaction, we carried out this reaction under 140 °C, and the
yield significantly improved to 93% (entry 11). To our delight, the
palladium catalyst loading could be reduced from 5 mol% to
3 mol% while the isolated yield increased to 97% (entry 12). Reduc-
ing the equivalent of 1a and Ag2CO3 resulted in slightly diminished
yields respectively (entry 13, 14). Moreover, control experiments
showed that Ag2CO3 (entry 15) and Pd(PtBu3)2 (entry 16) were
essential for this cross-coupling reaction. After evaluating other
commercially available oxidants, we have found that Ag2CO3 plays
a crucial role in this reaction owing to the oxidizing potentials and
solubility (For detail, see: Supporting Information, Table S1)
[18f,19a,b,20].
With the optimized condition (Table 1, entry 12) in hand, we
then proceeded to expand the substrate scope to various substi-
tuted sodium arylsulfinates (Scheme 2). Initially, a variety of
mono-substituted sodium arylsulfinates were examined to obtain
the corresponding arylstannane derivatives. This reaction by using
2a as the stannylation reagent has shown excellent functional
Considering about that this reaction is carried out under 140 °C,
it is presumed to proceed through radical mechanism. To gain
insights into the reaction mechanism, we have carried out the stan-
nylation reaction in the presence of radical scavenger TEMPO
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C. Lian et al. / Tetrahedron Letters xxx (2018) xxx–xxx
3
Scheme 2. Scope of substrates.
Scheme 3. Gram-scale synthetic procedure.a
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4
C. Lian et al. / Tetrahedron Letters xxx (2018) xxx–xxx
Scheme 4. Sequential stannylation and Pd-catalyzed Stille cross coupling reactions.a
Based on our investigation and the literature precedents, a pos-
sible mechanism was proposed to account for this Pd-catalyzed
cross-coupling reaction. As shown in Scheme 5, the catalytic cycle
starts with the oxidation of Pd(0) catalyst by using Ag2CO3 to form
Pd(Ⅱ) species, which then reacts with sodium arylsulfinate, provid-
ing palladium salt A. Elimination of SO2 from A generates aryl pal-
ladium intermediate B, followed by the transmetallation with ditin
reagent to give rise to the intermediate C. Subsequently, reductive
elimination from C produces desired arylstannane product along
with the generation of Pd(0) species. Finally, Pd(0) is oxidized by
Ag(I) to regenerate the catalytically active Pd(II) complex.
Conclusion
In conclusion, we have developed a new synthetic method
towards trialkyl arylstannanes through Pd-catalyzed desulfitative
cross-coupling reaction of sodium aryl sulfinates with distannanes.
The reaction features high efficiency with low catalyst loading,
good functional groups tolerance, affording stannylation products
with moderate to excellent yields. Besides, the starting materials
are easily prepared from the corresponding aryl sulfonyl chlorides.
Because of the importance of arylstannane compounds in Stille
cross-coupling reactions, we expect that this stannylation method
will demonstrate potential applications in organic synthesis.
Further expansion of the substrate scope as well as the detailed
mechanistic study is currently underway in our laboratory.
Scheme 5. Possible reaction mechanism.
(2,2,6,6-tetramethylpiperidine-1-oxyl). As shown in Eq. (1), 10 mol
%, 50 mol% and 1 equiv of TEMPO were respectively added under the
standard conditions. In all the cases, the product 3a was also
obtained in good yields. This experiment indicated that this cross-
coupling was not proceeding through the radical pathway.
,
,
,
t
Pd P B
(
u
A
TEMP
O
g2CO3
)
3 2
a
+
n u
S B
3
n
u
SO2N
B
S
(
)
3 2
,
DMA 140 oC 1 h
Acknowledgments
a
a
3
a
2
1
This work is supported by the scientific research funding of
Tianjin Normal University (5RL138), National Natural Science
Foundation of China (21602156), and Shanghai Sailing Program
(18YF1401800).
mo
mo
9
2
%
mo
e u v
1
q i
86
%
TEMP
3
0
l
10
l
50
91
l
O
%
%
%
a
9
7
%
%
ð1Þ
Please cite this article in press as: C. Lian et al., Tetrahedron Lett. (2018), https://doi.org/10.1016/j.tetlet.2018.09.065

C. Lian et al. / Tetrahedron Letters xxx (2018) xxx–xxx
5
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Appendix A. Supplementary data
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Please cite this article in press as: C. Lian et al., Tetrahedron Lett. (2018), https://doi.org/10.1016/j.tetlet.2018.09.065