Copper-Catalyzed Three Component Regio- and Stereospecific Selenosulfonation of Alkynes: Synthesis of (E)-β-Selenovinyl Sulfones

Article abstract of DOI:10.1021/acs.joc.6b03049

A copper-catalyzed highly regio- and stereospecific selenosulfonation of alkynes with arylsulfonohydrazides and diphenyl diselenide has been developed. This novel three component reaction proceeds under very mild conditions and with a broad scope of substrates, providing a wide range of (E)-β-selenovinyl sulfones in good to excellent yields.

Full text of DOI:10.1021/acs.joc.6b03049

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Note
Copper-catalyzed Three Component Regio- and Stereo-specific
Selenosulfonation of Alkynes: Synthesis of (E)-#-selenovinyl Sulfones
Yang Liu, Guangfan Zheng, Qian Zhang, Yan Li, and Qian Zhang
J. Org. Chem., Just Accepted Manuscript • DOI: 10.1021/acs.joc.6b03049 • Publication Date (Web): 26 Jan 2017
Downloaded from http://pubs.acs.org on January 27, 2017
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Copper-catalyzed Three Component Regio- and
Stereo-specific Selenosulfonation of Alkynes: Synthesis
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of (E)-β-selenovinyl Sulfones
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Yang Liu, Guangfan Zheng, Qian Zhang†, Yan Li*, and Qian Zhang†,*
Key Laboratory of Functional Organic Molecule Design & Synthesis of Jilin Province, Department
of Chemistry, Northeast Normal University, 5268 Renmin Street, Changchun, Jilin 130024, China
ABSTRACT: A copper-catalyzed high regio- and stereo-specific selenosulfonation of alkynes with
arylsulfonohydrazides and diphenyl diselenide has been developed. This novel three component
reaction proceed under very mild conditions and with a broad scope of substrates, providing a
wide range of (E)-β-selenovinyl sulfones in good to excellent yields.
Vinyl sulfones are unique motifs in some biologically active molecules1 and usefully synthetic
intermediates in organic synthesis.2 Accordingly, considerable effort has been devoted to develop
new and efficient methods for the construction of these compounds,3 including the oxidation of
the corresponding vinyl sulides,4 Knoevenagel condensation of aromatic aldehydes with
sulfonylacetic acids,5 Wittig reaction of α-sulfonyl phosphonium ylides,6 β-elimination of
selenosulfones or halosulfones,7 and sulfonation of alkenes8/alkynes.9-12 Among them, sulfonative
functionalization of alkynes, the addition of sulfonyl and other groups across a triple bond,
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represents one of the most straightforward strategies. For example, alkynes sulfonative
difunctionalization, such as halosulfonylation,9 sulfonyloxidation,10 sulfonamination11 and
sulfonylcarbonation,12 has been successfully realized for the synthesis of various sulfonative
difunctionalization products. Vinyl selenides13 are useful synthetic intermediates and therapeutic
entities that display a wide spectrum of biological activities, thus rendering these motifs highly
important synthetic targets.14 β-Selenovinyl sulfones could be obtained through radical
selenosulfonation of alkynes and Se-phenyl p-tolueneselenosulfonate (Scheme 1a),15 which
usually need to be pre-pared through the reaction of sulfinates, sulfonhydrazides, or selenenyl
halides with benzeneseleninic acid, or sodium sulfonates with diphenyl diselenide.16 Therefore,
the development of direct three component selenosulfonation reactions starting from readily
available sulfonyl and selenyl radical sources is highly desirable. In this context, Huang and
co-workers realized selenosulfonation of acetylenes with sodium arenesulfinates and diphenyl
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o
diselenide (Scheme 1b).17 However, these reaction were performed at 80 C and only terminal
alkynes were effect. Recently, we realized copper-catalyzed radical aminative functionalizations of
al-kynes.18 As our continuous interest in radical reactions,19 we expected to explore three
component radical selenosul-fonation of alkynes. Herein, we reported a novel copper-catalyzed
regio- and stereo-specific selenosulfonation of alkynes with arylsulfonohydrazides and diphenyl
diselenide under very mild conditions, synthesizing a wide range of (E)-β-selenovinyl sulfones
(Scheme 1b).
Scheme 1. Selenosulfonation of Alkynes
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Initially, the reaction of prop-1-yn-1-ylbenzene (1a, 0.3 mmol) with p-toluenesulfonyl
hydrazide (2a, 1.2 equiv.) and diphenyl diselenide (3, 0.5 equiv.) was chosen as model reaction to
o
optimize the conditions. No reaction occurred at 70 C in CH3CN without catalyst and oxidant
(Table 1, entry 1). In the presence of K2S2O8 (2 equiv.), to our delight, the desired
selenofulfonation product 4a was obtain in 43% yield (Table 1, entry 2). Upon adding
Cu(MeCN)4PF6 (5 mol%), 72% of 4a was obtained (Table 1, entry 3). Decreasing temperature to 50
oC, a better yield (92%) of 4a was given (Table 1, entry 4). Among CH3CN, DCE, CH3OH, DMF, THF
and toluene, CH3CN was the best solvent (Table 1, entries 4-9). Other oxidants, such as H2O2,
DTBP and TBHP were also examined, but the result was not improved (Table 1, entries 10-12).
Other copper-catalysts such as CuBr•Me2S, CuBr, CuCl, CuI and Cu(OAc)2 were not as efficient as
Cu(MeCN)4PF6 (Table 1, entries 13-17). Finally, we tried to conduct the reaction at room
temperature. Satisfactorily, the yield of 4a was improved to 98% (Table 1, entry 18), while in
absence of the catalyst no reaction was observed (Table 1, entry 19). The configurations of 4a was
further confirmed by X-ray analysis.20
Table 1. Optimization of Reaction Conditionsa
entry
catalyst
oxidant
solvent
T (oC)
yieldb (%)
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none
none
Cu(MeCN) PF
4
none
K2S2O8
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
H O
2 2
DTBP
TBHP
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
K S O
2 2 8
CH3CN
CH3CN
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70
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rt
0
43
72
92
68
35
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50
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0
CH CN
3
6
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6
6
6
6
6
6
6
6
3
Cu(MeCN) PF
CH CN
3
DCE
CH OH
3
DMF
4
4
Cu(MeCN) PF
4
Cu(MeCN) PF
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6
4
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Cu(MeCN) PF
4
Cu(MeCN) PF
7
8
THF
4
Cu(MeCN) PF
4
Cu(MeCN) PF
9
Toluene
CH CN
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4
3
Cu(MeCN) PF
4
Cu(MeCN) PF
CH CN
3
CH CN
70
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68
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45
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98
0
4
3
CH CN
3
CuBr•Me S
2
CH CN
CuBr
CuCl
CuI
3
CH CN
3
CH CN
3
Cu(OAc)
CH CN
3
2
Cu(MeCN) PF
4
none
CH CN
6
3
K S O
2 2 8
CH CN
3
rt
a
General reaction conditions: 1a (0.3 mmol), 2a (0.36 mmol), 3 (0.15 mmol), catalyst (5 mol%),
b
oxidant (0.6 mmol), solvent (2 mL), nitrogen atmosphere, 12 h. Ts = -SO2C6H4-p-CH3. Isolated
yield.
With the optimized reaction conditions (Table 1, entry 18), we next explored the scope of
the selenosulfonation process with respect to internal alkyes 1 and arylsulfonyl-hydrazides 2, the
results are shown in Table 2. Delightfully, the internal alkynes with alkyl (1a–e) or aryl (1e),
smoothly participated in this highly region- and stereo-selective selenosulfonation reaction to
provide (E)-β-selenovinyl sulfones 4a–e in moderate to excellent yields. It should be noted that a
synthetically attractive hydroxyl group, which is sensitive to oxidants survived from the reaction
conditions, gave the expected product 4d in an accepted yield (53%). The substrates 1f–m,
bearing either electron-donating or electron-withdrawing groups on the benzene ring, were
compatible with this reaction as well, regardless of their different electronic properties and sites,
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affording desired (E)-β-selenovinyl sulfones 4f–m in 53-88% yields. In addition, internal aliphatic
alkyne 1n successfully underwent selenosulfonylation to give 4n, albeit in a low yield. Next, the
scope of arylsulfonylhydrazides 2 was examined. Gratifyingly, introduction of methyoxyl, methyl
and halo-gen groups into the aromatic ring of sulfonylhydrazides was well-tolerated, and the
corresponding (E)-β-selenovinyl sulfones 4o-q were formed in good to excellent yield. It should
be noted that in all reactions, no other isomers were observed.
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Table 2. Scope of Internal Alkynes and Arylsulfonylhydrazidesa
a Reaction conditions: 1 (0.3 mmol), 2 (0.36 mmol), 3
(0.15 mmol), Cu(MeCN)4PF6 (5 mol%), K2S2O8 (0.6
mmol), CH3CN (2 mL), nitrogen atmosphere, room
temperature, 12 h. Isolated yield. Ts
-SO2C6H4-p-CH3
=
.
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Inspired by the above excellent results, we sent to explore the selenosulfonation of terminal
alkynes. As described in Table 3, aromatic terminal alkynes with a wide range of functional groups,
such as F, Cl, Br, CN, NO2, MeOCO, Me, Et and t-Bu, were well tolerated, producing
(E)-β-selenovinyl sulfones 6a-m in up to 95% yield. Gratifyingly, aliphatic alkynes 5n and 5o were
viable substrates for the selenosulfonation, producing 6n and 6o with a yield of 82% and 85%,
respectively. Significantly, aliphatic alkynes with Cl (5p), OH (5q) and TMS (5r) groups which can
readily undergo further transformation were founded to be suitable for the reaction, delivering
the desired (E)-β-selenovinyl sulfones 6p-r. The configurations of 6a and 6p were further
confirmed by X-ray analysis.20 Additionally, dimethyl diselenide was efficient for this reaction,
providing the corresponding selenosulfonation product 6s in 35% yield.
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Table 3. Variety of Terminal Alkynes and Disenidesa
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a
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Reaction conditions: 5 (0.3 mmol), 2a (0.36 mmol), 3
(0.15 mmol), Cu(MeCN)4PF6 (5 mol%), K2S2O8 (0.6
mmol), CH3CN (2 mL), nitrogen atmosphere, room
temperature, 12 h. Isolated yield. Ts = -SO2C6H4-p-CH3.
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In order to demonstrate the synthetic utility of the three component selenosulfonation of
alkynes with aryl sulfonyhydrzides and diphenyl diselenide, we performed this three component
reaction on a gram scale (Scheme 2). Pleasingly, 3.93 g (E)-β-selenovinyl sulfone 4a was isolated.
Scheme 2. Gram-scale Synthesis of (E)-β-Selenovinyl Sulfone
To gain some insights into the reaction mechanism, some control experiments were carried
out. As known, selenosulfonates might be formed from the reaction of arysulfonohydrazides with
diphenyl diselenide. Thus, the reaction of prop-1-yn-1-ylbenzene (1a) with Se-phenyl
p-tolueneselenosulfonate was performed under optimized conditions (Table 1, entry 18). No
reaction occurred and the substrate was recovered completely. This result showed that the
selenosufonation might not involve a selenosulfonate intermediate. Next, Adding 1 equiv. of BHT
and TEMPO to the reaction of 1a under standard conditions, the yield of 4a decreased to 17%
and 21%, respectively. With 2 equiv. of BHT and TEMPO, the selenosulfonation was completely
suppressed and no 4a was detected. These results suggested that this transformation might
proceed via a radical pathway.
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Based on the experimental results and literatures,7b,15a,15b, 21 a proposed radical mechanism
is shown in Scheme 3. Initially, the sulfonyl radical A was generated in the presence of copper salt
and K2S2O8 via single electron transfer and deprotonation process, along with the release of N2.22
Then, the sulfonyl radical A region-specifically added to alkynes, forming a relatively stable
β-sulfonyl vinyl radical B. Subsequently, the phenyl selenol group transferred from diphenyl
diselenide to B or coupled between B and phenyl selenol radical to afford thermodynamically
stable (E)-β-selenovinyl sulfone 4a. Alternatively, the phenyl selenol group transfer might be
much more rapid than the inversion of B,15b thus resulting in a single isomer 4a.
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Scheme 3. Proposed Mechanism
K2SO4
K2S2O8
B
SePh
PhSe
Cu(I)
Cu(II)
O
O
1a
O
S
NHNH2
S
Ts
Ts
O
N2
+
PhSeSePh
H
4a
2a
A
B
In conclusion, we have developed a copper-catalyzed high regio- and stereo-specific
selenosulfonation of alkynes with aryl sulfonohydrazides and diphenyl diselenide. This three
component reaction proceed under very mild conditions and with a broad scope of substrates.
With the reaction, a wide range of (E)-β-selenovinyl sulfones are synthesized in good to excellent
yields.
EXPERIMENTAL SECTION
General Experimental Methods. All the reagents were used as purchased from commercial
suppliers without further purification. Acetonitrile was distilled over calcium hydride before use.
Analytical thin layer chromatography (TLC) was performed on pre-coated alumina-backed silica
gel plates (0.2 mm thickness) which were developed using UV florescence. Flash chromatography
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was performed on silica gel (300−400 mesh). Melting points were measured on a standard
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melting point apparatus and are uncorrected. H NMR spectra were recorded on a 400, 500 or
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600 MHz spectrometer, while 13C NMR spectra were recorded on a 100, 125 and 150 MHz
instrument. Chemical shifts are reported in δ ppm referenced to an internal TMS standard for 1H
NMR and chloroform-d (δ = 77.0 ppm) for 13C NMR. HRMS spectra were recorded using FAB (TOF
analyzer) or ESI (TOF analyzer). Single-crystal X-ray diffraction data were recorded at a
temperature of 293(2) K on an Oxford Diffraction Gemini R Ultra diffractometer, using a ω scan
technique with Mo-Kα radiation (λ = 0.71073 Å).
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Characterization Data for Selenosulfonation Products. 4a, 4e and 6a were reported by Miura
and coworkers.15a 4n, 6a, 6d and 6j were reported by Back and coworkers.15b 4b−4d, 4f−4m,
4o−4q, 6b, 6c, 6e−6i, and 6k−6r were synthesized as follows.
General Procedure A for the Synthesis of Products 4 and 6. In a dried glass vial, equipped
with a magnetic stir bar, charged with PhSeSePh (46.8 mg, 0.15 mmol, 0.5 equiv.),
Cu(MeCN)4PF6 (5.6 mg, 5 mol%), K2S2O8 (162.2 mg, 0.6 mmol, 2.0 equiv.) under
nitrogen atmosphere, 2 mL MeCN was added next, followed by addition of alkyne 1
or 5 (0.3 mmol, 1.0 equiv.) and benzenesulfonyl hydrazide (0.36 mmol, 1.2 equiv.).
After stirring for 12 h, the reaction mixture was concentrated, then the residue was
subjected to column chromatography on silica gel (petroleum ether: diethyl ether =
40:1 – 12:1) to afford the desired product 4 or 6.
(E)-phenyl(1-phenyl-2-tosylprop-1-en-1-yl)selane (4a). 15a Following the general procedure A, 4a
1
was obtained as a white solid (98% yield, 125.8 mg). mp: 93−94 °C; H NMR (500 MHz, CDCl3) δ
7.37 (d, J = 8.5 Hz, 2H), 7.18 – 7.06 (m, 5H), 7.02 – 6.86 (m, 5H), 6.74 – 6.68 (m, 2H), 2.38 (s, 3H),
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2.36 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 151.0, 143.4, 138.3, 137.0, 135.9, 129.2, 129.1, 128.6,
128.5, 127.7, 127.3, 127.0, 126.7, 21.5, 18.7. HRMS (ESI-TOF) (m/z): Calcd for C22H20O2SSe ([M +
H]+), 429.0427, found 429.0422.
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(E)-phenyl(1-phenyl-2-tosylpent-1-en-1-yl)selane (4b). Following the general procedure A, 4b was
1
obtained as a white solid (93% yield, 127.2 mg). mp: 102−104 °C; H NMR (400 MHz, CDCl3) δ
7.21 (d, J = 8.4 Hz, 2H), 7.12 – 7.04 (m, 3H), 7.01 (d, J = 8.0 Hz, 2H), 6.98 – 6.85 (m, 3H), 6.80 (t, J =
7.6 Hz, 2H), 6.65 – 6.54 (m, 2H), 2.96 – 2.82 (m, 2H), 2.32 (s, 3H), 1.95 – 1.78 (m, 2H), 1.13 (t, J =
7.2 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 150.9, 143.0, 139.2, 138.6, 136.9, 129.3, 128.9, 128.5,
128.3, 127.4, 127.1, 126.8, 126.5, 35.2, 22.4, 21.4, 14.1. HRMS (ESI-TOF) (m/z): Calcd for
C24H24O2SSe ([M + Na]+), 479.0566, found 479.0567.
(E)-(3-methoxy-1-phenyl-2-tosylprop-1-en-1-yl)(phenyl)selane (4c). Following the general
procedure A, 4c was obtained as a yellow oil. (93% yield, 127.8 mg). 1H NMR (400 MHz, CDCl3) δ
7.28 (d, J = 8.4 Hz, 2H), 7.17 – 7.00 (m, 5H), 6.98 – 6.89 (m, 3H), 6.85 (t, J = 8.0 Hz, 2H), 6.66 (d, J =
7.2 Hz, 2H), 4.70 (s, 2H), 3.47 (s, 3H), 2.33 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 160.1, 143.2, 138.6,
136.8, 135.4, 135.3, 129.00, 128.96, 128.6, 128.4, 127.6, 127.2, 126.6, 70.0, 58.0, 21.4. HRMS
(ESI-TOF) (m/z): Calcd for C23H22O3SSe ([M + Na]+), 481.0368, found 481.0359.
(E)-1,3-diphenyl-3-(phenylselanyl)-2-tosylprop-2-en-1-ol (4d). Following the general procedure A,
4d was obtained as a white solid. (53% yield, 82.7 mg). mp: 170−171 °C; 1H NMR (400 MHz, CDCl3)
δ 7.68 (d, J = 8.0 Hz, 2H), 7.48 (t, J = 7.2 Hz, 2H), 7.38 (t, J = 7.6 Hz, 1H), 7.14 – 7.05 (m, 3H), 7.00 –
6.81 (m, 8H), 6.75 (dd, J = 19.2, 7.2 Hz, 2H), 6.51 (d, J = 10.8 Hz, 2H), 4.71 (d, J = 11.2 Hz, 1H), 2.29
(s, 3H). 13C NMR (151 MHz, CDCl3) δ 155.8, 143.4, 141.0, 140.7, 138.6, 137.0, 134.9, 129.8, 129.4,
128.9, 128.8, 128.6, 127.65, 127.63, 127.61, 126.82, 126.78, 126.6, 75.4, 21.5. HRMS (ESI-TOF)
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(m/z): Calcd for C28H24O3SSe ([M + Na]+), 543.0511, found 543.0515.
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(E)-(1,2-diphenyl-2-tosylvinyl)(phenyl)selane (4e). 15a Following the general procedure A, 4e was
obtained as a white solid. (42% yield, 61.7 mg). mp: 167−168 °C; 1H NMR (600 MHz, CDCl3) δ 7.46
– 7.40 (m, 3H), 7.38 – 7.34 (m, 2H), 7.27 – 7.22 (m, 2H), 7.10 – 7.03 (m, 5H), 7.03 – 6.99 (m, 3H),
6.94 – 6.89 (m, 4H), 2.35 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 154.8, 143.5, 138.0, 137.4, 137.1,
135.2, 134.7, 131.0, 129.3, 128.8, 128.5, 128.3, 127.7, 127.5, 126.9, 21.5. HRMS (ESI-TOF) (m/z):
Calcd for C27H22O2SSe ([M + H]+), 491.0589, found 491.0586.
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(E)-(1-(3,4-dimethylphenyl)-2-tosylpent-1-en-1-yl)(phenyl)selane (4f). Following the general
procedure A, 4f was obtained as a white solid. (79% yield, 114.7 mg). mp: 89−90 °C; 1H NMR (400
MHz, CDCl3) δ 7.20 (d, J = 8.4 Hz, 2H), 7.10 – 7.04 (m, 3H), 7.03 – 6.89 (m, 4H), 6.64 (d, J = 7.6 Hz,
1H), 6.49 (dd, J = 8.0, 1.6 Hz, 1H), 6.06 (s, 1H), 2.84 – 2.95 (m, 2H), 2.33 (s, 3H), 2.03 (s, 3H), 1.82
(m, 6H), 1.61 – 1.46 (m, 2H), 1.04 (t, J = 7.2 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 150.9, 142.7,
139.3, 138.9, 136.9, 135.5, 134.4, 133.1, 130.3, 128.6, 128.3, 128.1, 127.8, 127.6, 127.1, 33.0,
31.1, 22.9, 21.4, 19.3, 19.0, 13.8. HRMS (ESI-TOF) (m/z): Calcd for C26H27O2SSe ([M + Na]+),
506.0795, found 506.0791.
(E)-(1-(2-methoxyphenyl)-2-tosylpent-1-en-1-yl)(phenyl)selane (4g). Following the general
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procedure A, 4g was obtained as a white solid. (88% yield, 128.3 mg). mp: 99−100 °C; H NMR
(400 MHz, CDCl3) δ7.20 – 7.27 (m, 2H), 7.12 – 7.05 (m, 3H), 6.99 (d, J = 8.4 Hz, 2H), 6.96 – 6.83 (m,
4H), 6.64 (t, J = 7.6 Hz, 1H), 5.99 (d, J = 8.0 Hz, 1H), 3.19 (s, 3H), 2.81 (q, J = 4.0 Hz, 2H), 2.32 (s,
3H), 1.99 – 1.79 (m, 2H), 1.12 (t, J = 7.6 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 154.5, 148.7, 142.6,
138.4, 137.9, 137.3, 131.4, 129.5, 128.5, 127.9, 127.7, 126.6, 124.33, 119.0, 108.9, 54.0, 34.7,
22.0, 21.4, 14.1. HRMS (ESI-TOF) (m/z): Calcd for C25H26O3SSe ([M + Na]+), 509.0664, found
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(E)-(1-(2,4-difluorophenyl)-2-tosylpent-1-en-1-yl)(phenyl)selane (4h). Following the general
procedure A, 4h was obtained as a white solid. (75% yield, 110.7 mg). mp: 96−97 °C; 1H NMR (400
MHz, CDCl3) δ 7.39 (d, J = 8.4 Hz, 2H), 7.24 – 7.11 (m, 5H), 7.07 – 6.97 (m, 2H), 6.76 (td, J = 8.4,
6.4 Hz, 1H), 6.58 – 6.45 (m, 1H), 6.20 (td, J = 9.6, 2.4 Hz, 1H), 2.87 – 2.67 (m, 2H), 2.37 (s, 3H),
1.92 – 1.70 (m, 2H), 1.09 (t, J = 7.6 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 162.6 (dd, J = 298.6, 11.5
Hz), 157.8 (dd, J = 298.6, 14.7 Hz), 143.7, 140.2, 137.8, 137.3, 131.9 (dd, J = 9.6, 3.9 Hz), 129.2,
128.6, 127.5, 125.9, 120.4 (dd, J = 19.1, 3.6 Hz), 109.9 (dd, J = 21.4, 3.3 Hz), 102.7 (t, J = 25.5
Hz),102.52, 35.0, 21.8, 21.5, 14.1. HRMS (ESI-TOF) (m/z): Calcd for C24H22F2O2SSe ([M + Na]+),
515.0372, found 515.0377.
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(E)-N,N-diethyl-4-(1-(phenylselanyl)-2-tosylbut-1-en-1-yl)benzamide (4i). Following the general
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procedure A, 4i was obtained as a white solid. (66% yield, 109.9 mg). mp: 123−124 °C; H NMR
(400 MHz, CDCl3) δ 7.16 (d, J = 8.0 Hz, 2H), 7.13 – 6.98 (m, 5H), 6.96 – 6.88 (m, 2H), 6.78 – 6.71
(m, 2H), 6.59 (d, J = 8.0 Hz, 2H), 3.52 – 3.31 (bs, 2H), 2.97 – 2.78 (m, 4H), 2.29 (s, 3H), 1.92 – 1.77
(m, 2H), 1.19 – 1.01 (m, 6H), 1.02 – 0.85 (m, 3H). 13C NMR (151 MHz, CDCl3) δ 170.3, 149.4, 143.2,
140.0, 138.3, 137.1, 136.5, 136.0, 129.3, 129.0, 128.5, 128.4, 127.3, 126.7, 124.4, 35.1, 22.3, 21.3,
14.0. HRMS (ESI-TOF) (m/z): Calcd for C29H33NO3SSe ([M + Na]+), 578.1249, found 578.1245.
(E)-(1-(4-bromophenyl)-2-tosylpent-1-en-1-yl)(phenyl)selane (4j). Following the general procedure
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A, 4j was obtained as a white solid. (93% yield, 149.0 mg). mp: 132−133 °C; H NMR (600 MHz,
CDCl3) δ 7.27 – 7.22 (m, 3H), 7.15 (t, J = 7.2 Hz, 1H), 7.08 (t, J = 8.4 Hz, 4H), 7.00 (t, J = 7.8 Hz, 2H),
6.96 – 6.90 (m, 2H), 6.47 (d, J = 8.4 Hz, 2H), 2.91 – 2.82 (m, 2H), 2.36 (s, 3H), 1.90 – 1.77 (m, 2H),
1.11 (t, J = 7.2 Hz, 3H). 13C NMR (151 MHz, CDCl3) δ 149.0, 143.4, 140.4, 138.5, 137.0, 135.0,
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130.9, 129.9, 129.1, 128.7, 127.5, 126.6, 121.5, 35.3, 22.4, 21.5, 14.2. HRMS (ESI-TOF) (m/z):
Calcd for C24H23BrO2SSe ([M + H]+), 536.9826, found 536.9831.
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(E)-(1-(naphthalen-1-yl)-2-tosylpent-1-en-1-yl)(phenyl)selane (4k). Following the general
procedure A, 4k was obtained as a white solid. (85% yield, 129.1 mg). mp: 77−78 °C; 1H NMR (400
MHz, CDCl3) δ 7.49 – 7.37 (m, 3H), 7.25 – 7.18 (m, 2H), 7.04 (t, J = 6.8 Hz, 1H), 7.01 – 6.91 (m, 3H),
6.90 – 6.83 (m, 1H), 6.81 – 6.73 (m, 2H), 6.69 – 6.56 (m, 4H), 3.12 – 2.91 (m, 2H), 2.13 – 1.97 (m,
5H), 1.23 (t, J = 7.2 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 149.3, 142.6, 140.2, 137.3, 137.1, 132.4,
132.2, 129.9, 128.5, 128.4, 128.2, 127.6, 127.5, 127.4, 126.0, 125.7, 125.13, 125.11, 123.9, 34.8,
22.3, 21.1, 14.3. HRMS (ESI-TOF) (m/z): Calcd for C28H26O2SSe ([M + Na]+), 529.0716, found
529.0723.
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(E)-(5-chloro-1-(p-tolyl)-2-tosylpent-1-en-1-yl)(phenyl)selane (4l). Following the general procedure
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A, 4l was obtained as a white solid. (86% yield, 130.0 mg). mp: 108−109 °C; H NMR (600 MHz,
CDCl3) δ 7.23 (d, J = 7.8 Hz, 2H), 7.13 – 7.05 (m, J = 14.9, 7.8 Hz, 3H), 7.03 (d, J = 8.4 Hz, 2H), 6.94
(t, J = 7.8 Hz, 2H), 6.63 (d, J = 7.8 Hz, 2H), 6.49 (d, J = 8.4 Hz, 2H), 3.72 (t, J = 6.6 Hz, 2H), 3.07 –
2.98 (m, 2H), 2.37 – 2.28 (m, 5H), 2.13 (s, 3H). 13C NMR (150 MHz, CDCl3) δ 152.5, 143.2, 138.4,
137.4, 137.2, 136.9, 132.7, 129.1, 128.9, 128.5, 128.4, 127.5, 127.3, 126.8, 44.6, 31.5, 30.9, 21.4,
21.1. HRMS (ESI-TOF) (m/z): Calcd for C26H27ClO2SSe ([M + Na]+), 541.0489, found 541.0485.
(E)-(2-cyclopropyl-1-(p-tolyl)-2-tosylvinyl)(phenyl)selane (4m). Following the general procedure A,
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4m was obtained as a white solid. (87% yield, 122.2 mg). mp: 105−106 °C; H NMR (400 MHz,
CDCl3) δ 7.46 (d, J = 8.4 Hz, 2H), 7.19 – 7.05 (m, 5H), 6.98 (t, J = 7.6 Hz, 2H), 6.77 – 6.65 (m, 4H),
2.35 (s, 3H), 2.16 (s, 3H), 1.23 – 1.15 (m, 3H), 1.03 – 0.94 (m, 2H). 13C NMR (126 MHz, CDCl3) δ
155.6, 143.0, 138.8, 137.5, 136.3, 133.1, 129.2, 128.9, 128.1, 127.7, 127.5, 21.5, 21.1, 13.6, 10.5.
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HRMS (ESI-TOF) (m/z): Calcd for C25H24O2SSe ([M + Na]+), 491.0561, found 491.0569.
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(E)-phenyl(4-tosylhex-3-en-3-yl)selane (4n).
Following the general procedure A, 4n was
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obtained as a white solid. (47% yield, 55.6 mg). mp: 56−57 °C; 1H NMR (600 MHz, CDCl3) δ 7.77 (d,
J = 7.8 Hz, 2H), 7.55 (d, J = 7.2 Hz, 2H), 7.39 (t, J = 7.8 Hz, 1H), 7.36 – 7.29 (m, 4H), 2.74 – 2.63 (m,
4H), 2.44 (s, 3H), 1.15 (t, J = 7.8 Hz, 3H), 0.86 (t, J = 7.2 Hz, 3H). 13C NMR (151 MHz, CDCl3) δ 155.7,
143.9, 139.3, 137.5, 136.4, 129.7, 129.4, 129.1, 127.3, 127.0, 27.4, 26.7, 21.6, 14.6, 13.6. HRMS
(ESI-TOF) (m/z): Calcd for C19H22O2SSe ([M + Na]+), 417.0408, found 417.0410.
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(E)-(2-((4-methoxyphenyl)sulfonyl)-1-phenylprop-1-en-1-yl)(phenyl)selane (4o). Following the
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general procedure A, 4o was obtained as a white solid. (79% yield, 105.2 mg). mp: 87−88 °C; H
NMR (400 MHz, CDCl3) δ 7.40 (d, J = 8.8 Hz, 2H), 7.14 – 7.08 (m, 3H), 7.03 – 6.87 (m, 5H), 6.79 (d,
J = 9.2 Hz, 2H), 6.75 – 6.68 (m, 2H), 3.81 (s, 3H), 2.38 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 162.9,
150.5, 136.9, 136.0, 132.8, 129.7, 129.1, 128.6, 128.4, 127.3, 126.7, 113.8, 55.5, 18.7. HRMS
(ESI-TOF) (m/z): Calcd for C22H20O3SSe ([M + Na]+), 467.0197, found 467.0205.
(E)-(2-(mesitylsulfonyl)-1-phenylprop-1-en-1-yl)(phenyl)selane (4p). Following the general
procedure A, 4p was obtained as a white solid. (82% yield, 112.2 mg). mp: 92−93 °C; 1H NMR (600
MHz, CDCl3) δ 7.11 – 7.05 (m, 3H), 6.93 (t, J = 7.8 Hz, 2H), 6.79 (t, J = 7.8 Hz, 1H), 6.70 (t, J = 7.8 Hz,
2H), 6.63 (s, 2H), 6.56 (d, J = 7.2 Hz, 2H), 2.42 (s, 3H), 2.29 (s, 6H), 2.17 (s, 3H). 13C NMR (151 MHz,
CDCl3) δ 147.7, 142.0, 139.1, 137.0, 135.6, 135.5, 135.0, 131.5, 128.7, 128.5, 128.4, 127.1, 127.0,
126.6, 21.9, 20.8, 17.8. HRMS (ESI-TOF) (m/z): Calcd for C26H28O2SSe ([M + Na]+), 507.0879, found
507.0871.
(E)-(2-((4-chlorophenyl)sulfonyl)-1-phenylprop-1-en-1-yl)(phenyl)selane (4q). Following the
general procedure A, 4q was obtained as a white solid. (75% yield, 100.8 mg). mp: 125−126 °C; 1H
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NMR (600 MHz, CDCl3) δ 7.34 (d, J = 8.4 Hz, 2H), 7.26 (d, J = 2.4 Hz, 1H), 7.11 – 7.05 (m, 2H), 6.99
– 6.92 (m, 3H), 6.89 (t, J = 7.2 Hz, 2H), 6.66 (d, J = 7.2 Hz, 2H), 2.42 (s, 3H). 13C NMR (151 MHz,
CDCl3) δ 152.1, 139.9, 139.1, 137.0, 135.5, 132.5, 129.2, 129.0, 128.8, 128.7, 128.5, 127.5, 126.9,
18.5. HRMS (ESI-TOF) (m/z): Calcd for C21H17ClO2SSe ([M + Na]+), 470.9705, found 470.9708.
(E)-phenyl(1-phenyl-2-tosylvinyl)selane (6a).15a, 15b Following the general procedure A, 6a was
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obtained as a white solid. (95% yield, 118.0 mg). mp: 150−151 °C; H NMR (600 MHz, CDCl3) δ
7.61 – 7.55 (m, 2H), 7.46 – 7.42(m, 1H), 7.41 – 7.37 (m, 2H), 7.36 – 7.23 (m, 5H), 7.21 – 7.15 (m,
2H), 7.10 (d, J = 8.4 Hz, 2H), 6.16 (s, 1H), 2.36 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 157.1, 143.5,
136.5, 134.6, 130.12, 130.09, 129.24, 129.23, 128.4, 127.8, 127.4, 126.8, 125.8, 21.5. HRMS
(ESI-TOF) (m/z): Calcd for C21H18O2SSe ([M + Na]+), 437.0089, found 437.0100.
(E)-(1-(4-fluorophenyl)-2-tosylprop-1-en-1-yl)(phenyl)selane (6b). Following the general procedure
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A, 6b was obtained as a white solid. (82% yield, 106.3 mg). mp: 113−115 °C; H NMR (400 MHz,
CDCl3) δ 7.56 (d, J = 6.8 Hz, 2H), 7.48 – 7.29 (m, 5H), 7.7.23 – 7.12 (m, 4H), 6.96 (t, J = 8.8 Hz, 2H),
6.19 (s, 1H), 2.38 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 163.2 (d, J = 248.0), 155.8, 143.7, 138.7,
136.5, 130.59 (d, J = 9.0 Hz), 130.15, (d, J = 5.4 Hz), 129.3, 127.3, 126.7, 126.5, 115.0 (d, J = 22.0),
114.9, 21.5. HRMS (ESI-TOF) (m/z): Calcd for C21H17FO2SSe ([M + Na]+), 454.9998, found
454.9998.
(E)-(1-(4-chlorophenyl)-2-tosylprop-1-en-1-yl)(phenyl)selane (6c). Following the general procedure
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A, 6c was obtained as a white solid. (92% yield, 123.6 mg). mp: 122−123 °C; H NMR (600 MHz,
CDCl3) δ 7.58 – 7.52 (m, 2H), 7.46 – 7.41 (m, 1H), 7.38 (t, J = 7.2 Hz, 2H), 7.34 (d, J = 8.4 Hz, 2H),
7.25 – 7.22 (m, 2H), 7.17 – 7.11 (m, 4H), 6.18 (s, 1H), 2.39 (s, 3H). 13C NMR (151 MHz, CDCl3) δ
155.4, 143.9, 138.7, 136.5, 135.5, 133.1, 130.2, 129.9, 129.4, 128.1, 127.4, 126.5, 21.5. HRMS
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(ESI-TOF) (m/z): Calcd for C21H17ClO2SSe ([M + H]+), 448.9877, found 448.9873.
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procedure A, 6d was obtained as a white solid. (77% yield, 113.6 mg). mp: 144−145 °C; H NMR
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(500 MHz, CDCl3) δ 7.55 (d, J = 7.0 Hz, 2H), 7.45 – 7.36 (m, 5H), 7.33 (d, J = 8.0 Hz, 2H), 7.14 (d, J =
8.0 Hz, 2H), 7.06 (d, J = 8.0 Hz, 2H), 6.16 (s, 1H), 2.38 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 155.4,
143.9, 138.6, 136.5, 133.6, 131.0, 130.2, 130.1, 129.4, 127.4, 126.5, 126.4, 123.7, 21.6. HRMS
(ESI-TOF) (m/z): Calcd for C21H17BrO2SSe ([M + Na]+), 514.9190, found 514.9193.
(E)-4-(1-(phenylselanyl)-2-tosylprop-1-en-1-yl)benzonitrile (6e). Following the general procedure A,
6e was obtained as a white solid. (63% yield, 83.0 mg). mp: 128−129 °C; 1H NMR (400 MHz, CDCl3)
δ 7.62 – 7.49 (m, 4H), 7.48 – 7.42 (m, 1H), 7.41 – 7.33 (m, 4H), 7.32 – 7.25 (m, 2H), 7.19 (d, J = 7.6
Hz, 2H), 6.23 (s, 1H), 2.40 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 153.9, 144.3, 139.6, 138.4, 136.6,
131.5, 130.4, 130.3, 129.6, 129.2, 127.3, 126.9, 125.9, 118.3, 112.8, 21.6. HRMS (ESI-TOF) (m/z):
Calcd for C22H17NO2SSe ([M + H]+), 440.0224, found 440.0228.
(E)-(1-(3-chlorophenyl)-2-tosylprop-1-en-1-yl)(phenyl)selane (6f). Following the general procedure
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CDCl3) δ 7.58 (d, J = 7.2 Hz, 2H), 7.49 – 7.36 (m, 3H), 7.32 (d, J = 8.4 Hz, 2H), 7.24 (t, J = 8.0 Hz, 2H),
7.15 (d, J = 8.0 Hz, 3H), 6.94 (s, 1H), 6.20 (s, 1H), 2.40 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 155.0,
144.0, 138.5, 136.6, 136.2, 133.8, 130.3, 130.2, 129.2, 128.0, 127.4, 126.89, 126.86, 126.3, 21.5.
HRMS (ESI-TOF) (m/z): Calcd for C21H17ClO2SSe ([M + H]+), 448.9887, found 448.9873.
(E)-(1-(3-nitrophenyl)-2-tosylvinyl)(phenyl)selane (6g) Following the general procedure A, 6g was
obtained as a white solid. (42% yield, 57.8 mg). mp: 162−163 °C; 1H NMR (400 MHz, CDCl3) δ 8.16
(d, J = 8.0 Hz, 1H), 7.80 (s, 1H), 7.63 (d, J = 7.6 Hz, 1H), 7.57 (d, J = 7.0 Hz, 2H), 7.51 (t, J = 8.0 Hz,
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1H), 7.46 (t, J = 7.2 Hz, 1H), 7.39 (t, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 7.17 (d, J = 8.0 Hz, 2H),
6.28 (s, 1H), 2.38 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 153.4, 147.5, 144.4, 138.3, 136.6, 136.4,
134.8, 130.5, 130.3, 129.6, 129.0, 127.5, 127.3, 125.9, 123.8, 123.0, 21.5. HRMS (ESI-TOF) (m/z):
Calcd for C21H17NO4SSe ([M + H]+), 460.0123, found 460.0128.
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(E)-(1-(2-chlorophenyl)-2-tosylvinyl)(phenyl)selane (6h) Following the general procedure A, 6h was
obtained as a white solid. (68% yield, 91.4 mg). mp: 124−125 °C; 1H NMR (400 MHz, cdcl3) δ7.57 –
7.52 (m, 2H), 7.47 – 7.31 (m, 5H), 7.25 – 7.22 (m, 2H), 7.17 – 7.11 (m, 4H), 6.18 (s, 1H), 2.38 (s,
3H). 13C NMR (126 MHz, CDCl3) δ 154.9, 143.9, 138.4, 136.5, 136.2, 133.7, 130.2, 130.2, 129.3,
129.1, 127.9, 127.4, 126.8, 126.8, 126.2, 21.5. HRMS (ESI-TOF) (m/z): Calcd for C21H17ClO2SSe ([M
+ H]+), 448.9881, found 448.9878.
(E)-methyl 2-(1-(phenylselanyl)-2-tosylvinyl)benzoate (6i) Following the general procedure A, 6i
was obtained as a yellow oil. (86% yield, 121.8 mg). 1H NMR (400 MHz, CDCl3) δ 7.92 (d, J = 7.6,
1H), 7.59 – 7.53 (m, 2H), 7.46 – 7.35 (m, 3H), 7.34 – 7.27 (m, 4H), 7.12 (d, J = 8.8 Hz, 3H), 6.24 (s,
1H), 3.75 (s, 3H), 2.35 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 165.4, 156.2, 143.6, 138.4, 136.6,
135.9, 131.5, 130.4, 130.0, 129.8, 129.8, 129.2, 128.9, 128.3, 127.5, 126.7, 124.8, 51.8, 21.4.
HRMS (ESI-TOF) (m/z): Calcd for C23H20O4SSe ([M + H]+), 473.0326, found 473.0328.
(E)-phenyl(1-(p-tolyl)-2-tosylvinyl)selane (6j).15b Following the general procedure A, 6j was
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obtained as a white solid. (94% yield, 120.7 mg). mp: 162−163 °C; H NMR (600 MHz, CDCl3) δ
7.574 (d, J = 6.6 Hz, 2H), 7.46 – 7.41 (m, 1H), 7.38 (t, J = 7.2 Hz, 2H), 7.33 (d, J = 7.8 Hz, 2H), 7.14 –
7.06 (m, 6H), 6.10 (s, 1H), 2.37 (s, 3H), 2.36 (s, 3H). 13C NMR (151 MHz, CDCl3) δ 157.4, 143.5,
139.5, 139.0, 136.5, 131.7, 130.1, 130.0, 129.2, 128.5, 128.4, 127.4, 127.1, 125.4, 21.5, 21.4.
HRMS (ESI-TOF) (m/z): Calcd for C22H20O2SSe ([M + Na]+), 451.0277, found 451.0271.
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(s, 1H), 2.64 (q, J = 8.0 Hz, 2H), 2.35 (s, 3H), 1.24 (t, J = 7.6 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ
157.4, 145.7, 143.4, 138.8, 136.5, 131.8, 130.1, 130.0, 129.1, 128.5, 127.4, 127.3, 127.0, 125.6,
28.7, 21.5, 15.5. HRMS (ESI-TOF) (m/z): Calcd for C23H22O2SSe ([M + Na]+), 465.0406, found
465.0398.
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(E)-(1-(4-(tert-butyl)phenyl)-2-tosylprop-1-en-1-yl)(phenyl)selane (6l) Following the general
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procedure A, 6l was obtained as a white solid. (85% yield, 119.9 mg). mp: 121−122 °C; H NMR
(400 MHz, CDCl3) δ 7.58 (d, J = 6.8 Hz, 2H), 7.46 – 7.34 (m, 3H), 7.26 – 7.20 (m, 4H), 7.08 (d, J =
8.0 Hz, 2H), 7.02 (d, J = 8.0 Hz, 2H), 6.13 (s, 1H), 2.32 (s, 3H), 1.30 (s, 9H). 13C NMR (126 MHz,
CDCl3) δ 157.3, 152.5, 143.2, 138.7, 136.6, 131.5, 130.2, 130.0, 129.0, 128.2, 127.5, 126.9, 125.9,
124.7, 34.7, 31.2, 21.5. HRMS (ESI-TOF) (m/z): Calcd for C25H26O2SSe ([M + H]+), 471.0898, found
471.0892.
(E)-phenyl(1-(m-tolyl)-2-tosylvinyl)selane (6m) Following the general procedure A, 6m was
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obtained as a white solid. (86% yield, 110.4 mg). mp: 109−110 °C; H NMR (400 MHz, CDCl3) δ
7.62 – 7.56 (m, 2H), 7.47 – 7.35 (m, 3H), 7.32 – 7.26 (m, 2H), 7.17 (t, J = 7.6 Hz, 1H), 7.10 (t, J = 7.2
Hz, 3H), 7.03 (d, J = 7.2 Hz, 1H), 6.86 (s, 1H), 6.13 (s, 1H), 2.36 (s, 3H), 2.26 (s, 3H). 13C NMR (126
MHz, CDCl3) δ 157.4, 143.4, 138.9, 137.5, 136.6, 134.43, 130.2, 130.1, 130.0, 129.1, 128.7, 127.8,
127.5, 125.7, 125.6, 21.5, 21.2. HRMS (ESI-TOF) (m/z): Calcd for C22H20O2SSe ([M + Na]+),
451.0251, found 451.0242.
(E)-phenyl(4-phenyl-1-tosylbut-1-en-2-yl)selane (6n) Following the general procedure A, 6n was
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obtained as a white solid. (82% yield, 108.7 mg). mp: 90−91 °C; 1H NMR (500 MHz, CDCl3) δ 7.65
(d, J = 8.0 Hz, 2H), 7.54 (d, J = 7.0 Hz, 2H), 7.44 (t, J = 7.5 Hz, 1H), 7.38 (t, J = 7.5 Hz, 2H), 7.33 –
7.24 (m, 4H), 7.22 (d, J = 7.5 Hz, 3H), 5.94 (s, 1H), 3.11 (q, J =5.0 Hz, 2H), 2.97 –2.89 (m, 2H), 2.41
(s, 3H). 13C NMR (126 MHz, CDCl3) δ 159.1, 144.0, 139.2, 136.6, 136.5, 130.0, 129.9, 129.8, 129.2,
128.4, 127.1, 127.0, 126.1, 124.9, 38.3, 21.5. HRMS (ESI-TOF) (m/z): Calcd for C23H22O2SSe ([M +
H]+), 443.0586, found 443.0579.
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(E)-phenyl(1-tosylhex-1-en-2-yl)selane (6o) Following the general procedure A, 6o was obtained as
a white solid. (85% yield, 100.5 mg). mp: 68−69 °C; 1H NMR (400 MHz, CDCl3) δ 7.67 (d, J = 8.0 Hz,
2H), 7.54 – 7.49 (m, 2H), 7.45 – 7.33 (m, 3H), 7.28 (d, J = 8.4 Hz, 2H), 5.85 (s, 1H), 2.83 (t, J = 8.0
Hz, 2H), 2.41 (s, 3H), 1.60 – 1.49 (m, 2H), 1.42 – 1.29 (m, 2H), 0.89 (t, J = 7.2 Hz, 3H). 13C NMR
(126 MHz, CDCl3) δ 161.4, 143.8, 139.6, 136.7, 130.0, 129.9, 129.7, 126.9, 125.9, 123.7, 33.0, 32.1,
22.5, 21.5, 13.8. HRMS (ESI-TOF) (m/z): Calcd for C19H22O2SSe ([M + Na]+), 417.0403, found
417.0398.
(E)-(6-chloro-1-tosylhex-1-en-2-yl)(phenyl)selane (6p) Following the general procedure A, 6p was
obtained as a white solid. (88% yield, 113.0 mg). mp: 90−91 °C; 1H NMR (400 MHz, CDCl3) δ 7.67
(d, J = 8.4 Hz, 2H), 7.55 – 7.50 (m, 2H), 7.44 (t, J = 7.2 Hz, 1H), 7.38 (t, J = 7.2 Hz, 2H), 7.30 (d, J =
8.0 Hz, 2H), 5.90 (s, 1H), 3.54 (t, J = 6.4 Hz, 2H), 2.88 (t, J = 7.6 Hz, 2H), 2.43 (s, 3H), 1.87 – 1.68 (m,
4H). 13C NMR (151 MHz, CDCl3) δ 160.0, 144.01, 133.99, 139.5, 136.7, 130.1, 130.0, 129.8, 126.9,
125.8, 124.4, 44.5, 32.2, 32.0, 27.3, 21.6. HRMS (ESI-TOF) (m/z): Calcd for C19H21ClO2SSe ([M +
H]+), 429.0195, found 429.0191.
(E)-1-(1-(phenylselanyl)-2-tosylvinyl)cyclohexanol (6q) Following the general procedure A, 6q was
obtained as a white solid. (73% yield, 95.5 mg). mp: 56−58 °C; 1H NMR (400 MHz, CDCl3) δ 7.62 (d,
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J = 8.4 Hz, 2H), 7.46 (d, J = 7.6 Hz, 2H), 7.38 (t, J = 7.2 Hz, 1H), 7.31 (t, J = 7.6 Hz, 2H), 7.28 – 7.22
(m, 2H), 5.54 (s, 1H), 4.83 (s, 1H), 2.41 (s, 3H), 2.09 – 1.90 (m, 4H), 1.87 – 1.68 (m, 3H), 1.66 –
1.55 (m, 2H). 13C NMR (151 MHz, CDCl3) δ 169.6, 143.9, 138.5, 136.6, 130.1, 129.8, 129.6, 127.6,
126.9, 122.7, 76.3, 36.2, 25.0, 21.5, 21.3. HRMS (ESI-TOF) (m/z): Calcd for C21H24O3SSe ([M + Na]+),
459.0508, found 459.0504.
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(E)-trimethyl(1-(phenylselanyl)-2-tosylvinyl)silane (6r) Following the general procedure A, 6r was
obtained as a white solid. (64% yield, 78.7 mg). mp: 81−82 °C; 1H NMR (400 MHz, CDCl3) δ 7.56 (d,
J = 8.4 Hz, 2H), 7.45 – 7.30 (m, 5H), 7.24 (d, J = 8.4 Hz, 2H), 6.04 (s, 1H), 2.40 (s, 3H), 0.49 (s, 9H).
13C NMR (151 MHz, CDCl3) δ 159.9, 143.7, 138.5, 136.8, 131.6, 130.1, 129.8, 129.7, 126.9, 126.7,
21.5, 0.5. HRMS (ESI-TOF) (m/z): Calcd for C18H22O2SSeSi ([M + Na]+), 433.0174, found 433.0167.
(E)-methyl(1-phenyl-2-tosylvinyl)selane (6s) Following the general procedure A, 6s was obtained
as a yellow oil. (35% yield, 43.5 mg). 1H NMR (600 MHz, CDCl3) δ 7.39 (d, J = 8.4 Hz, 2H), 7.34 (t, J
= 7.2 Hz, 1H), 7.28 (t, J = 7.8 Hz, 2H), 7.13 (d, J = 7.8 Hz, 4H), 6.44 (s, 1H), 2.38 (s, 3H), 2.15 (s, 3H).
13C NMR (150 MHz, CDCl3) δ 156.1, 143.6, 138.9, 135.2, 129.3, 129.2, 128.2, 127.8, 127.5, 124.8,
21.5, 8.6. HRMS (ESI-TOF) (m/z): Calcd for C16H16O2SSe ([M + K]+), 390.9668 , found 390.9643.
ASSOCIATED CONTENT
Supporting Information
Crystallographic data for 4a, 6a and 6p (CIF), and spectral data for new compounds. The
Supporting Information is available free of charge on the ACS Publications web-site.
AUTHOR INFORMATION
Corresponding Author
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*E-mail: liy078@nenu.edu.cn
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*E-mail: zhangq651@nenu.edu.cn
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Notes
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The authors declare no competing financial interest.
† These authors are different persons.
ACKNOWLEDGMENT
We acknowledge the financial support for this work from the National NSF of China (21172033,
21372041 and 21302017), Changbai Mountain Scholarship Program, and the Fundamental
Research Funds for the Central Universities (2412016KJ006).
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