Solid-phase organic synthesis of aryl vinyl ethers using sulfone-linking strategy

Article abstract of DOI:10.1002/cjoc.201100451

A novel facile solid-phase organic synthesis of aryl vinyl ethers by reaction of polystyrene-supported 2-phenylsulfonylethanol with phenols under Mitsunobu conditions and subsequent elimination reaction with DBU has been developed. The advantages of this method include straightforward operation, good yield and high purity of the products. Alternatively, a typical example of Suzuki coupling reaction on-resin was further applied to prepare 4-phenylphenyl vinyl ether for extending this method.

Full text of DOI:10.1002/cjoc.201100451

FULL PAPER
DOI: 10.1002/cjoc.201100451
Solid-Phase Organic Synthesis of Aryl Vinyl Ethers Using
Sulfone-Linking Strategy
Yu, Lamei(余腊妹)
Tang, Ni(汤妮)
Sheng, Shouri*(盛寿日)
Chen, Rubing(陈茹冰)
Liu, Xiaoling(刘晓玲)
Cai, Mingzhong(蔡明中)
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, China
A novel facile solid-phase organic synthesis of aryl vinyl ethers by reaction of polystyrene-supported
-phenylsulfonylethanol with phenols under Mitsunobu conditions and subsequent elimination reaction with DBU
2
has been developed. The advantages of this method include straightforward operation, good yield and high purity of
the products. Alternatively, a typical example of Suzuki coupling reaction on-resin was further applied to prepare
4
-phenylphenyl vinyl ether for extending this method.
Keywords solid-phase organic synthesis, aryl vinyl ether, polystyrene-supported 2-phenylsulfonylethanol, sul-
fone-linking, Suzuki coupling reaction
Introduction
synthesis (SPOS) method has been popularly developed
[
17]
for the synthesis of small molecule libraries.
The
Vinyl ethers are highly versatile intermediates in or-
ganic synthesis that can be used universally in a series
of chemical transformations. More specifically, aryl
vinyl ethers with unsubstituted vinyl moiety have wide
synthetic applications and are employed as key interme-
SPOS approach offers the advantage of driving the re-
action to completion by using excess of reagents, and
easy isolation of products by filtration from the solid
support. Sulfinate-functionalized resins have been effi-
ciently prepared and utilized in SPOS and the resulting
[
1]
[
2]
diates for the generation of new polymeric materials,
as dienophiles for cycloaddition reactions such as [2＋
sulfone linker has been found to be both a robust and a
[17c]
versatile linker.
Previous and recent reports of Kurth
[
3]
[4]
[5]
2
],
[2 ＋ 4]
and 1,3-dipolar cycloadditons,
in
[18]
[19]
and co-workers,
Lam’s research group,
other
[
6]
[7]
cyclopropanations, hydroformylations and in natural
product analogue synthesis. Generally, the dehydro-
halogenation of aryl 2-haloethyl ethers and the addi-
tion of phenols to acetylene
[20]
[21]
laboratories
and ours
have developed sulfone-
[
8]
linking strategies for SPOS methods to explore sul-
[
9]
[22]
fone-based chemical transformations.
[
10]
under strong base and
Although the synthesis of aryl vinyl ethers in solu-
tion-phase has been largely investigated, conversely
there is a paucity of solid-phase synthetic approaches
elevated temperature conditions were used to access
these compounds. However, such reaction conditions
are unsuitable for sensitive substrates. In addition, the
copper(II)-promoted coupling of arylboronic acids with
[23]
for these structures. As part of an ongoing research
program focused on the use of sulfone linker in SPOS,
we report here an efficient solid-phase synthetic meth-
odology for the preparation of aryl vinyl ethers (Scheme
[11]
phenols,
tion with phenols, the transformations with Cu(OAc)
mediated coupling of 2,4,6-trivinylcyclotriboroxane as a
vinyl acetate in an iridium-catalyzed reac-
[
12]
2
1
).
[
13]
[14]
vinylboronic acid equivalent, tributy(vinyl)tin with
phenols and other reagents or methods
[
15]
were also
Experimental
utilized for similar transformation. Though some meth-
ods in the literature provide good yields, most of them
suffer from limitations such as harsh reactions, labori-
ous manipulation and low overall yields, or in some
cases, reactions are unsuitable for sensitive substrates,
vigorous toxic compounds are used or some reagents are
not readily available.
4
Melting points were determined on an X melting
1
13
point apparatus and are uncorrected. H and C NMR
spectra were recorded on a Bruker Avance (400 MHz)
3
spectrometer, using CDCl as the solvent and TMS as
an internal standard. FTIR spectra were taken on a
Perkin-Elmer SP One FTIR spectrophotometer. Poly-
styrene/1% divinylbenzene sodium sulfinate (1.80 mmol
Based on resin-supported synthesis of peptides de-
veloped by Merrifield in 1963,
[16]
solid-phase organic
2
SO Na/g) was purchased from Tianjin Nankai Hecheng
*
E-mail: shengsr@jxnu.edu.cn; Tel.: 0086-0791-88120619; Fax: 0086-0791-88506404
Received October 4, 2011; accepted November 29, 2011; published online April 10, 2012.
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc.201100451 or from the author.
Chin. J. Chem. 2012, 30, 1027—1030
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1027

Yu et al.
FULL PAPER
Scheme 1 Solid-phase synthetic route to aryl vinyl ethers
dimethyl sulphoxide, water, methanol, ether and di-
chloromethane (10 mL×2 for each) to provide 3a—3k.
Then, DBU (249 μL, 1.65 mmol) was added to the sus-
pension of 3a—3k in dichloromethane (20 mL). After
stirring at room temperature for 8 min, the resin was
filtrated and washed with dichloromethane (10 mL×3).
The collected dichloromethane layer was washed with
5% potassium hydrogen sulfate, saturated sodium hy-
drogen carbonate and brine (20 mL×2 for each), and
then dried over anhydrous magnesium sulfate and con-
O
ClCH CH OH
2
2
OH
SO Na
S
2
TBAI, KI
DMF/THF, 80 oC
O
1
2
R
R
HO
O
S
O
DIPAD, PPh , NMM, r.t.
3
O
3
R
centrated under reduced pressure and the crude products
DBU
1
4
a—4k were obtained and directly analyzed by H
O
CH Cl , r.t.
2
2
NMR and HPLC without further purification.
[14]
1
4
Phenyl vinyl ether (4a):
CDCl , 400 MHz) δ: 7.17—7.03 (m, 5H), 6.60 (dd, J＝
4.0, 6.0 Hz, 1H), 4.71 (dd, J＝14.0, 1.5 Hz, 1H), 4.35
Colorless oil; H NMR
(
1
3
Science and Technology Co. (100—200 mesh, Catalog
no. HC8201-1). The other chemicals were obtained
from commercial suppliers (Aldrich, USA and Shanghai
Chemical Company, China) and used without purifica-
tion.
1
3
(
dd, J＝6.0, 1.5 Hz, 1H); C NMR (CDCl
3
, 100 MHz)
δ: 154.2, 144.5, 133.0, 120.6, 115.2, 95.4; IR (film) ν:
－
1
1
638 cm .
-Methoxyphenyl vinyl ether (4b): Colorless oil;
H NMR (CDCl , 400 MHz) δ: 6.97 (d, J＝8.4 Hz, 2H),
[26]
4
1
3
Preparation of polymer-supported 2-phenylsulfonyl-
ethanol (2)
6
4
1
1
.85 (d, J＝8.4 Hz, 2H), 6.59 (dd, J＝14.2, 6.4 Hz, 1H),
.66 (dd, J＝14.2, 2.0 Hz, 1H), 4.35 (dd, J＝6.4, 2.0 Hz,
Resin 1 (1.0 g, 1.8 mmol) was swollen in a mixture
of DMF (5 mL) and THF (10 mL) by gently shaking the
resin-DMF-THF mixture at room temperature for 30
min. Then 2-chloroethanol (1.2 mL), tetrabutylammo-
nium iodide (0.15 g), and potassium iodide (0.9 g) were
added to this mixture and the resulting reaction mixture
was shaken at 80 ℃ under nitrogen atmosphere for 48
h. After filtration, the resin was washed successively
with DMF, water, methanol and ether (10 mL×2 for
each), and then dried under reduce pressure over phos-
phorous pentoxide at 50—60 ℃ to afford resin 2 as
yellow beads.
13
H), 3.80 (s, 3H); C NMR (CDCl
3
, 100 MHz) δ: 155.5,
45.7, 120.6, 117.9, 115.3, 95.6, 55.3; IR (film) ν: 1632
－1
cm .
[13]
2
-Methoxyphenyl vinyl ether (4c):
Colorless oil;
1
H NMR (CDCl
3
, 400 MHz) δ: 7.20—6.88 (m, 4H),
6
.52 (dd, J＝14.0, 6.2 Hz, 1H), 4.65 (dd, J＝14.0, 1.8
1
3
Hz, 1H), 4.32 (dd, J＝6.2, 1.8 Hz, 1H), 3.80 (s, 3H); C
NMR (CDCl , 100 MHz) δ: 150.3, 149.5, 145.6, 124.6,
21.1, 118.9, 113.0, 94.4, 55.8; IR (film) ν: 1638 cm .
3
－
1
1
[
10]
1
3
-Methylphenyl vinyl ether (4d): Colorless oil; H
NMR (CDCl , 400 MHz) δ: 7.22—6.86 (m, 4H), 6.52
dd, J＝13.8, 6.2 Hz, 1H), 4.33 (dd, J＝13.8, 1.8 Hz,
3
(
1
For analytical purposes the 3,5-dinitrobenzoate of
resin 2 was prepared by reaction of resin 2 (0.5 g) with
1
3
H), 4.05 (dd, J＝6.2, 1.8 Hz, 1H), 2.30 (s, 3H);
C
NMR (CDCl
22.5, 119.4, 115.2, 95.5, 21.6; IR (film) ν: 1640 cm .
3
, 100 MHz) δ: 154.5, 140.5, 132.2, 123.8,
3
,5-dinitrobenzoyl chloride (0.5 g) in dry pyridine (10
－
1
1
mL). After stirring at 80 ℃ for 1.5 h, the resin was
collected on a filter and washed successively with THF,
water, methanol and ether (5 mL×2 for each), and
dried as described above to yield the corresponding
[
9d]
1
4
-t-Butylphenyl vinyl ether (4e): Colorless oil; H
NMR (CDCl , 400 MHz) δ: 6.82 (d, J＝8.4 Hz, 2H),
.21 (d, J＝8.4 Hz, 2H), 6.53 (dd, J＝14.0, 6.0 Hz, 1H),
.30 (dd, J＝14.0, 1.8 Hz, 1H), 4.25 (dd, J＝6.0, 1.8 Hz,
3
7
4
3
,5-dinitrobenzoate resin (0.64 g) having a strong car-
1
3
－
1
3
1H), 1.33 (s, 9H); C NMR (CDCl , 100 MHz) δ: 157.0,
bonyl absorption at 1732 cm in its FTIR spectrum.
Anal. calcd N 3.50 (2.50 mequiv. N/g). The functional
loading of resin 2 could be calculated from this analysis
1
1
45.6, 133.8, 120.2, 117.5, 95.9, 38.1, 28.7; IR (film) ν:
－
1
639 cm .
-Bromophenyl vinyl ether (4f): Colorless oil; H
NMR (CDCl , 400 MHz) δ: 7.42 (d, J＝8.4 Hz, 2H),
.98 (d, J＝8.4 Hz, 2H), 6.62 (dd, J＝13.8, 6.2 Hz, 1H),
4.80 (dd, J＝13.8, 1.8 Hz, 1H), 4.50 (dd, J＝6.2, 1.8 Hz,
[
14]
1
4
2 2
and corresponded to 1.65 mequiv. of CH H OH func-
3
tional group per gram.
6
General procedure for the preparation of aryl vinyl
ethers 4a—4k
1
3
1
H); C NMR (CDCl
3
, 100 MHz) δ: 155.8, 147.5,
－
1
To resin 2 (1.0 g, 1.65 mmol) swelled in THF(5 mL)
at room temperature for 30 min was added a solution of
triphenylphosphine (1.6 g, 6.0 mmol) and phenols (5.0
mmol) in 4-methylmorpholine (10 mL). Neat diethyl
azodicarboxylate (790 μL, 5.0 mmol) was added in
small portions over a period of 5 min. After the suspen-
sion was shaken for 16 h at room temperature, the resin
132.5, 118.3, 115.8, 95.8; IR (film) ν: 1637 cm .
4-Chlorophenyl vinyl ether (4g): Colorless oil; H
NMR (CDCl , 400 MHz) δ: 7.45 (d, J＝8.4 Hz, 2H),
[27]
1
3
7.03 (d, J＝8.4 Hz, 2H), 6.64 (dd, J＝13.8, 6.0 Hz, 1H),
4.83 (dd, J＝13.8, 1.8 Hz, 1H), 4.52 (dd, J＝6.0, 1.8 Hz,
1
3
1H); C NMR (CDCl
3
, 100 MHz) δ: 156.1, 148.0,
－
1
132.9, 119.2, 116.3, 95.7; IR (film) ν: 1636 cm .
[
14]
3
a—3k was filtered and washed subsequently with THF,
4-Nitrophenyl vinyl ether (4h):
Pale yellow oil;
1028
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© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2012, 30, 1027—1030

Solid-Phase Organic Synthesis of Aryl Vinyl Ethers Using Sulfone-Linking Strategy
1
H NMR (CDCl
3
, 400 MHz) δ: 8.30 (d, J＝8.8 Hz, 2H),
monitoring for the appearance of the expected large hy-
－
1
7
5
1
1
.15 (d, J＝8.8 Hz, 2H), 6.68 (dd, J＝14.0, 6.0 Hz, 1H),
.04 (dd, J＝14.0, 2.0 Hz, 1H), 4.70 (dd, J＝6.0, 2.0 Hz,
droxyl stretch at 3500 cm , as well as the characteristic
－
1
sulfone absorption bands at 1317 and 1119 cm . Be-
1
3
H); C NMR (CDCl
3
, 100 MHz) δ: 161.2, 145.7,
sides, the hydroxyl group attachment on the resin 2 was
calculated to be 1.65 mmol CH CH OH/g from the ni-
2 2
－
1
42.9, 125.6, 116.2, 99.3; IR (film) ν: 1640, 1528 cm .
4
[14]
1
-Cyanophenyl vinyl ether (4i): Colorless oil; H
NMR (CDCl , 400 MHz) δ: 7.72 (d, J＝8.8 Hz, 2H),
.12 (d, J＝8.8 Hz, 2H), 6.68 (dd, J＝13.8, 6.0 Hz, 1H),
.99 (dd, J＝13.8, 2.0 Hz, 1H), 4.70 (dd, J＝6.0, 2.0 Hz,
trogen elemental analysis of its corresponding
3,5-dinitrobenzoate ester intermediate prepared by
treatment of 2 with 3,5-dinitrobenzoyl chloride accord-
3
7
4
1
1
[
24]
ing to the method described in literature.
Then, the
1
3
H); C NMR (CDCl
3
, 100 MHz) δ: 160.0, 145.9,
etherification reaction was investigated from resin 2
with phenol by means of the Mitsunobu reaction. After
a considerable number of experiments, the reaction was
carried out with triphenylphosphine and diisopropyl
azadicarboxylate (DIPAD) as reagents in N-methyl-
morpholine (NMM) as solvent using previously similar
34.3, 118.5, 117.2, 106.0, 98.5; IR (film) ν: 2206, 1635
－
1
cm .
-Methoxycarbonylphenyl vinyl ether (4j):
orless oil; H NMR (CDCl
8
6
J＝6.0, 1.8 Hz, 1H), 3.85 (s, 3H); C NMR (CDCl
1
9
[
14]
4
Col-
, 400 MHz) δ: 7.96 (d, J＝
.4 Hz, 2H), 7.18 (d, J＝8.4 Hz, 2H), 6.86 (dd, J＝13.8,
.0 Hz, 1H), 4.87 (dd, J＝13.8, 1.8 Hz, 1H), 4.56 (dd,
1
3
[25]
reported method
to give polymer-supported
13
3
,
2-phenoxyethyl phenyl sulfone (3a), which could not be
reliably analyzed on the FTIR. However, the complete
conversion of the hydroxy group of resin 2 to 3a was
further confirmed by treating 3a with acetyl chlo-
ride/triethylamine: no acetoxy absorption band was ob-
served in the FTIR spectrum of the product. Finally, a
number of elimination conditions were evaluated, and
optimal results were obtained by treating the resin 3a in
dichloromethane with an equimolar of 1,8-diazabicyclo-
[5.4.0]undec-7-ene (DBU) at room temperature for 8
min to provid phenyl vinyl ether (4a) in 95% yield and
00 MHz) δ: 166.8, 160.0, 146.8, 131.4, 124.6, 116.0,
7.2, 52.0; IR (film) ν: 1712, 1636 cm .
－
1
[
28]
1
-Naphthyl vinyl ether (4k):
White solid, m.p.
1
3
(
1
2—33 ℃; H NMR (CDCl
3
, 400 MHz) δ: 7.52—7.01
m, 7H), 6.72 (dd, J＝14.0, 6.0 Hz, 1H), 4.80 (dd, J＝
13
4.0, 1.6 Hz, 1H), 4.46 (dd, J＝6.0, 1.6 Hz, 1H);
, 100 MHz) δ: 152.8, 145.0, 133.8, 132.5,
28.8, 128.6, 128.3, 126.8, 125.8, 123.6, 115.6, 95.6; IR
C
NMR (CDCl
1
3
－
1
(KBr) ν: 1630 cm .
Typical procedure for the preparation of 4-phenyl-
phenyl vinyl ether (6)
9
7% purity of the crude product without further purifi-
cation (Table 1, Entry 1).
To 2-(4-bromophenoxy)ethyl phenyl sulfone resin
(3f) (1.0 g) swelled in DMF (10 mL) at room tempera-
Table 1 Yields and purities of aryl vinyl ethers 4a—4k
ture for 30 min were added Pd(OAc) (37 mg, 0.165
2
a
b
a
b
Entry
R (Phenol)
H
Product Yield /%
Purity /%
mmol), phenylboronic acid (731 mg, 6.0 mmol) and
CsF (912 mg, 6 mmol) in one portion, and the mixture
was heated to 80 ℃ for 24 h under nitrogen atmos-
phere. After completion of the reaction, the mixture was
cooled to room temperature, diluted with 25% aqueous
ammonium acetate (10 mL), stirred for 5 min, and fil-
tered. The resin was washed successively with DMF,
water, THF, dichloromethane and ether (20 mL×2 for
each) to furnish the resin 5, and then cleaved from the
support as described above to afford the Suzuki cou-
pling product, 4-phenylphenyl vinyl ether 6.
1
2
3
4
5
6
7
8
9
4a
4b
4c
4d
4e
4f
95
93
92
95
91
92
90
88
90
88
92
97
95
96
98
95
95
96
95
96
95
96
3
4-CH O
2-CH O
3
4-t-C H
4
9
4-Br
4-Cl
4-NO2
4g
4h
4i
4-CN
4-CO CH
2
3
[
13]
4
-Phenylphenyl vinyl ether (6): White solid, m.p.
1
1
0
1
4-CO CH
3
4j
1
2
5
1—52 ℃; H NMR (CDCl
3
, 400 MHz) δ: 7.67—7.36
1-Naphthol
4k
(
m, 7H), 7.14—7.10 (m, 2H), 6.82 (dd, J＝13.8, 6.0 Hz,
a
Overall yields based on polystyrene-supported sodium sulfinate
1 (1.80 mmol/g). Determined by HPLC of crude cleavage prod-
uct (λ＝254 nm).
1
1
1
9
H), 4.74 (dd, J＝13.8, 1.6 Hz, 1H), 4.48 (dd, J＝6.0,
b
13
.6 Hz, 1H); C NMR (CDCl
3
, 100 MHz) δ: 156.5,
48.0, 140.8, 136.4, 128.9, 128.6, 127.4, 126.6, 117.7,
－
1
5.7; IR (KBr) ν: 1642 cm .
Seen from Table 1, this method was found to be
generally applicable to a variety of substituted phenols
regardless of an electron-donating (Entries 2—5) or
electron-withdrawing (Entries 6—10) groups at the
phenyl ring, and the corresponding products were ob-
tained in good to high yields (88%—95%) with excel-
lent purities (95%—98%). Additionally, 1-naphthol also
afforded the corresponding product 4k effectively (En-
try 11).
Results and Discussion
As outlined in Scheme 1, polystyrene/1% divinyl-
benzene sodium sulfinate (1) was allowed to react with
2
-chloroethanol in DMF-THF (V∶V＝1∶2) in the
presence of tetrabutylammonium iodide (TBAI) and
potassium iodide to afford polymer-supported 2-phenyl-
sulfonylethanol (2), which was amenable to FTIR
Chin. J. Chem. 2012, 30, 1027—1030
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1029

Yu et al.
FULL PAPER
On the basis of the above results, the typical Suzuki
reaction of the polymer-supported 2-(4-bromophenoxy)-
ethyl phenyl sulfone (3f) with phenylboronic acid was
further investigated to expand the scope of this method-
ology. As shown in Scheme 2, treatment of 3f with
[3] For selected examples of [2＋2] cylcoadditons, see: (a) Futamura, S.;
Ohta, H.; Kamiya, Y. Bull. Chem. Soc. Jpn. 1982, 55, 2190; (b)
Brűckner, R.; Huisgen, R. Tetrahedron Lett. 1990, 31, 2557; (c)
El-Nabi, H. A. A. Tetrahedron 1997, 53, 1813.
[
4] For selected examples of Diels-Alder reactions, see: (a) Hojo, M.;
Masuda, R.; Okada, E. Synthesis 1990, 347; (b) Markó, I. E.; Evans,
G. R.; Declercq, J.-P. Tetrahedron 1994, 50, 4557; (c) Wada, E.;
Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 145.
2
phenylboronic acid in the presence of Pd(OAc) and
cesium fluoride under nitrogen in DMF at 80 ℃ for 24
h gave the resin 5. Subsequent washing of the resin 5
with DMF, water, THF, dichloromethane, and ether
successively, and then treatment of the resin 5 using the
same cleavage protocol as above yielded the corre-
sponding 4-phenylphenyl vinyl ether (6) in 86% yield
and 92% purity.
[5] For selected examples of 1,3-dipolar cycloadditons, see: (a) Shimizu,
T.; Hayashi, Y.; Teramura, K. J. Org. Chem. 1983, 48, 3053; (b)
Savinov, S. N.; Austin, D. J. J. Chem. Soc., Chem. Commun. 1999,
1
813.
[
6] Maligres, P. E.; Waters, M. M.; Lee, J.; Reamer, R. A.; Askin, D.;
Ashwood, M. S.; Cameron, M. J. Org. Chem. 2002, 67, 1093.
7] Ajjou, A. N.; Alper, H. J. Am. Chem. Soc. 1998, 120, 1466.
8] Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2003, 5,
[
[
Scheme 2 Suzuki reaction of resin 3f with phenylboronic acid
1
301.
[
9] (a) Oae, S.; Yano, Y. Tetrahedron 1968, 24, 5721; (b) Fueno, T.;
Matsumura, I.; Okuyama, T.; Furukawa, J. Bull. Chem. Soc. Jpn.
1968, 41, 818; (c) Dombroski, J. R.; Hallensleben, M. L. Synthesis
C H B(OH) , Pd(OAc)
2
O
S
6
5
2
O
Br
o
CsF, DMF, 80 C
O
1
972, 693; (d) Mizuno, K.; Kimura, Y.; Otsuji, Y. Synthesis 1979,
88; (e) McClelland, R. A. Can. J. Chem. 1977, 55, 548.
3
f
6
[
10] Reppe, W. Liebigs Ann. Chem. 1956, 601, 8.
[11] Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39,
937.
12] Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2002, 124,
590.
[13] Mckinley, N. F.; O’Shea, D. F. J. Org. Chem. 2004, 69, 5087.
O
S
O
2
O
[
5
1
DBU
CH Cl , r.t.
O
[
[
14] Blouin, M.; Frenette, R. J. Org. Chem. 2001, 66, 9043.
15] For recent review, see: Winternheimer, D. J.; Shade, R. E.; Merlic, C.
A. Synthesis 2010, 2497.
2
2
6
[
[
16] Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
17] For reviews, see: (a) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K.
Synthesis 1997, 1217; (b) Guillier, F.; Orain, D.; Bradley, M. Chem.
Rev. 2000, 100, 2091; (c) Sammelson, R. E.; Kurth, M. J. Chem. Rev.
2001, 101, 137; (d) Blaney, P.; Grigg, R.; Sridharan, V. Chem. Rev.
Conclusions
In summary, we report an efficient method for the
SPOS of aryl vinyl ethers employing polymer-supported
-phenylsulfonylethanol. Compared to previously re-
2
002, 102, 2607.
[
[
18] (a) Cheng, W. C.; Lin, C. C.; Kurth, M. J. Tetrahedron Lett. 2002,
2
4
4
3, 2967; (b) Cheng, W. C.; Kurth, M. J. J. Org. Chem. 2002, 67,
387; (c) Hwang, S. H.; Olmstead, M. M.; Kurth, M. J. J. Comb.
ported methods, this new method offers some advan-
tages such as straightforward operation, high yield and
purity of the products. Additionally, a typical example
for the preparation of 4-phenylphenyl vinyl ether
on-resin using Suzuki coupling reaction and release
from the support was described for extending this
methodology. Further investigations based on the poly-
meric 2-phenylsulfonylethanol reagent are now in pro-
gress.
Chem. 2004, 6, 142.
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W. W.; Lam, Y. L. J. Comb. Chem. 2005, 7, 721; (c) Gao, Y.-N.;
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W. W.; Lam, Y. L. J. Comb. Chem. 2005, 7, 721; (c) Gao, Y.-N.;
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Acknowledgement
This work was supported by the National Natural
Science Foundation of China (No. 21062007) and the
Research Program of Jiangxi Province Department of
Education (No. GJJ10385, GJJ11380).
[
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