FeCl3-catalyzed three-component aryl-selenylation of alkenes

Article abstract of DOI:10.1016/j.tet.2021.132239

FeCl₃-catalyzed three-component aryl-selenylation of alkenes with good to excellent yields has been disclosed. This method is characterized by synthesis of complicated products in a single-step reaction, simple operation and readily available commercially reagents. Finally, a reasonable mechanism of FeCl₃-catalyzed aryl-selenylation is proposed.

Full text of DOI:10.1016/j.tet.2021.132239

Tetrahedron xxx (xxxx) xxx
Contents lists available at ScienceDirect
Tetrahedron
journal homepage: www.elsevier.com/locate/tet
FeCl3-catalyzed three-component aryl-selenylation of alkenes
Chao Xu, Ze He**, Hongqin Yang, Hongyi Chen, Qingle Zeng*
State Key Laboratory of Geohazard Prevention and Geoenvironment Protection, College of Materials, Chemistry & Chemical Engineering, Chengdu University
of Technology, Chengdu, 610059, China
a r t i c l e i n f o
a b s t r a c t
Article history:
FeCl3-catalyzed three-component aryl-selenylation of alkenes with good to excellent yields has been
disclosed. This method is characterized by synthesis of complicated products in a single-step reaction,
simple operation and readily available commercially reagents. Finally, a reasonable mechanism of FeCl3-
catalyzed aryl-selenylation is proposed.
Received 10 April 2021
Received in revised form
11 May 2021
Accepted 13 May 2021
Available online xxx
© 2021 Elsevier Ltd. All rights reserved.
Keywords:
Aryl-selenylation
Selenium
Three-component reaction
Alkenes
FeCl3
1. Introduction
intermediates of electrophilic, nucleophilic and free radical [16].
In recent years, bifunctionalization of substituted olefins with
Selenium-containing compounds play a pivotal role in organic
synthesis [1], pharmaceutical chemistry [2], material science [3]
and biochemistry [4]. Organoselenium compounds can be used as
electrophilic reagents [5], nucleophiles [6], organic synthesis cat-
alysts [7] and ligands [8]. Under relatively mild reaction conditions,
the formations of CeLi bond [9], C-halogen bonds [10], CeH bond
[11] and CeC bond [12] are influenced by organoselenium com-
pounds. Because of these characteristics, organoselenium chemis-
try attracts widespread attention. A series of selenium-containing
compounds which show diverse pharmacological activities [13]
including antioxidant, enzyme mimics and inhibition, immune
regulation, cell protection, anti-tumor, anti-inflammatory, anti-
hypertension and anti-infection have been synthesized [14].
It is still a challenge to develop efficient methods to introduce
selenium-containing groups into organic molecules [15]. Among
various selenium compounds, dialkyl and diaryl diselenides have
excellent characteristics such as stability, easy access, and easy
operation, so researchers choose diselenides as the preferred
selenylation agent. Moreover, the selenium-selenium bond in dis-
elenide is easily oxidized, reduced or homogenized to generate
electrophiles and nucleophiles is an effective multi-component
method for the synthesis of complicated organic molecules [17].
The use of diselenides for the formation of carbon-heteroatom
bonds has been fully demonstrated by this mean, but there are
relatively few studies on electrophilic organoselenide reagents for
carbon-carbon bond formation [18]. Akio Toshimitsu et al. reported
reaction of phenyl ether with chiral alcohols containing 2-pyridinyl
selenyl as the substrate to obtain the corresponding substitution
product (Scheme 1a) [19]. Tang et al. prepared selenium-containing
compounds
with
simple
alkenes
using
trimethylsilyl
trifluoromethane-sulfonate (TMSOTf) as a catalyst and N-phenyl-
selenophthalimide (NPSP) as an efficient selenium source (Scheme
1b) [20]. However, this reaction must be performed at ꢀ78 ꢁC low
temperature which is harsh and difficult to fulfill in scale-up and
production. Besides, the above reaction also requires the con-
sumption of a good deal of catalysts.
During our on-going study on organochalcogen chemistry [21],
we occasionally discovered a three-component aryl-selenylation of
alkenes using FeCl3 as a catalyst with stable, abundant, low toxicity,
economic and ecological advantages [22].
2. Results and discussion
* Corresponding author.
** Corresponding author.
Initially, styrene (1a), 1,3,5-trimethoxybenzene (2a) and diaryl
diselenide (3a) were selected as substrates and FeCl3 as a catalysts.
E-mail addresses: heze@cdut.edu.cn (Z. He), qlzeng@cdut.edu.cn (Q. Zeng).
https://doi.org/10.1016/j.tet.2021.132239
0040-4020/© 2021 Elsevier Ltd. All rights reserved.
Please cite this article as: C. Xu, Z. He, H. Yang et al., FeCl3-catalyzed three-component aryl-selenylation of alkenes, Tetrahedron, https://doi.org/
10.1016/j.tet.2021.132239

C. Xu, Z. He, H. Yang et al.
Tetrahedron xxx (xxxx) xxx
dimethoxybenzene,
1,2-dimethoxybenzene,
1-methoxy-3,5-
dimethylbenzene and 1,2,3-trimethoxy-5-methylbenzene were
alkylated indeed exclusively at the 4-position, despite the slightly
lower yield (4aca-4afa). Then, electron-rich arene containing hy-
droxyl group also afforded excellent yield (4aga). Accordingly, our
studies indicate that aryl-selenylation is more likely to occur if
there are more donor substituents on the benzene ring. Finally, it
was remarkable that indole also provided the corresponding
product (aha) with good to excellent yield.
Next, we studied the scope of substrates 1 and 2 in this three-
component reaction (Table 3). A series of styrene derivatives with
various substituents on the aromatic ring were proved to be suit-
able candidates in this transformation. Both with electron-donating
and electron-withdrawing groups at para-position on the benzene
ring fulfilled this reaction smoothly, but it was a pity that these
aromatic styrenes with the electron-donating groups (4baa-4daa)
had lower yields than the electron-withdrawing groups (4eaa-
4faa, 4gaa and 4haa). Combination of para-halogen-substituted
styrenes (1f-1h) with electron-rich aromatic hydrocarbons (2a-2d)
produced a series of desirable products (4faa-4fda, 4gaa-4gda and
4haa-4hda) with good to excellent yields. Interestingly, for the
same electron-rich arene and PhSeSePh, yields increased in accord
with the halogen atom size of para-halogen-substituted styrenes.
Finally, we investigated the reactivity of various diaryl dis-
elenides 3. As shown in Table 4, diaryl diselenides both with
electron-donating and electron-withdrawing groups gave the
desired products in good yields. A range of functional groups, such
as alkyl, alkoxy, trifluoromethyl and halogen on the para-position,
showed excellent tolerance in the reaction (4aab-4aaf). Addition-
ally, the corresponding products could also be obtained for the
substitution of ortho-chloro and meta-methyl substituted diaryl
diselenides (4aah-4aai).
To demonstrate the utility of this protocol, we conducted the
reaction between 1a (5.0 mmol, 0.52g), 2a (6.0 mmol,1.01 g) and 3a
(5.0 mmol, 1.57g) in the presence of FeCl3 (0.1 mmol) on a gram
scale (Scheme 2). Much to our delight, the corresponding product
4aaa was obtained up to 81% isolated yield which demonstrated
this protocol could be used as a practical method.
After the successful demonstration of FeCl3-catalyzed difunc-
tionalization of alkenes with diaryl diselenides and electron-rich
arenes, in order to probe the mechanism of this transformation,
several control experiments were investigated.
Scheme 1. Methods of synthesis of asymmetric (2,2-diarylethyl)(aryl)selanes.
The desired 4aaa with a yield of 55% was obtained in MeCN as a
solvent at 60 ꢁC (Table 1, entry 1). And other iron salts and copper
salts gave lower yields than FeCl3 (entries 2e5). Consequently,
other Lewis acids were screened, but the results were not satis-
factory (entries 6e7). Gladly, when the temperature was raised to
80 ꢁC, the yield increased significantly, reaching 88% (entries 8e10).
Nevertheless, other solvents such as DMSO, DMF, water, and
toluene all gave poorer results (entries 11e14). Increase of time to
24 h or decrease to 6 h did not afford higher yield (entry 15).
Therefore, the optimized condition for the synthesis of 4aaa was
obtained: styrene 1a (1.0 equiv.), 1,3,5-trimethoxybenzene 2a (1.2
equiv.), diphenyl diselenide 3a (1.0 equiv.), FeCl3 (0.1 mmol) under
air in CH3CN (4 mL) at 80 ꢁC for 12 h.
With the optimized condition in hand, we set out to explore the
scope of the substrates. Firstly, various electron-rich arenes 2 were
investigated (Table 2). Among the experiments, the yield of 1,3,5-
trimethoxybenzene alkylation was the highest (4aaa). Interest-
ingly, the aryl-selenylation of 1,2,4-trimethoxybenzene preferen-
tially occurred at the 5-position (4aba). As expected, 1,3-
Table 1
Screening of reaction conditionsa.
In the beginning, 2,2,6,6-tetramethylpiperidinyl-1-oxy (TEMPO)
was added to investigate whether the reaction was a free radical
reaction [21,23]. Nevertheless, this reaction was hardly influenced
by TEMPO and gave nearly the same yield (79%) as that under the
optimized condition (Scheme 3, eqn. a). This suggests that this
reaction was not a free radical reaction process.
Entry
Catalyst
Solvent
Temp. (ꢁC)
Yield (%)
1
2
3
4
5
6
7
8
FeCl3
FeCl2
Fe(NO)3
CuBr2
CuI
ZnCl2
AlCl3
FeCl3
FeCl3
FeCl3
FeCl3
FeCl3
FeCl3
FeCl3
FeCl3
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
DMSO
DMF
60
60
60
60
60
60
60
r.t
40
80
80
80
80
80
80
55
40
trace
37
35
trace
34
trace
43
88
trace
22
Subsequently, electrophilic aromatic substitution product 5aa
was generated by the reaction of electron-rich arene 1,3,5-
trimethoxylbenzene and diphenyl diselenide under the optimized
condition, indicating that phenylselenium cation (PhSeþ) was
ready to generate from diphenyl diselenide under such a condition,
and then reacted with electron-rich arenes to provide 5aa (Scheme
3, eqn. b). However, the reaction could not proceed without the
addition of FeCl3 catalyst, showing that FeCl3 might promote the
dissociation of selenium-selenium bond of diphenyl diselenide to
generate phenylselenium cation (Scheme 3, eqn. c).
Based on the control experimental results and related reports
[24], a possible pathway for the difunctionalization of alkenes is
proposed as shown in Scheme 4. Taking the model reaction as an
example, firstly, diphenyl diselenide 3a are catalyzed by FeCl3 to
generate phenylseleno cation and a complex of phenylselenolate
and FeCl3. Due to the oxidation of air, the complex might be turned
into diphenyl diselenide via oxidative coupling reaction and thus
9
10a
11
12
13
14
15c,d
Toluene
Water
MeCN
37
trace
85(61)
b Isolated yield.
a
Conditions: 1a (0.50 mmol), 2a (0.60 mmol), 3a (0.50 mmol), catalyst
(0.1 mmol), MeCN (4 mL), at 80 ꢁC for 12 h, unless otherwise noted.
c
Reaction time 24 h.
Reaction time 6 h.
d
2

C. Xu, Z. He, H. Yang et al.
Tetrahedron xxx (xxxx) xxx
Table 2
Scope of the substrate electron-rich arenes (2)a.
Table 3
Scope of the substrates 1 and 2a.
FeCl3 is restored. While phenylseleno cation adds to styrene 1a via
electrophilic addition to olefins to give an organic selenium cationic
intermediate 5 and its tautomer 5’. Then, intermediate 5 is attacked
by electron-rich arenes 2a to produce intermediate 6. Eventually,
intermediate 6 loses a proton to get product 4aaa.
3. Conclusions
In summary, we have developed a FeCl3-catalyzed method for
three-component aryl-selenylation of alkenes with good to excel-
lent yields, which is characterized by synthesis of complicated
products in a single-step reaction, simple operation and readily
available commercially reagents. This method has a good yield in
gram-scale reaction. A reasonable mechanism that is based on
3

C. Xu, Z. He, H. Yang et al.
Tetrahedron xxx (xxxx) xxx
Table 4
Substrate scope of diaryl diselenidesa.
Scheme 2. Gram-scale aryl-arylselenization of alkenes.
Scheme 4. A plausible mechanism.
purification from the commercial supplier's products. 1H NMR
spectra were determined on a Bruker Avance III 400 MHz instru-
ment. 1H NMR data are reported in
d units (ppm), and were
measured relative to the signals for residual chloroform (7.26 ppm)
in the deuterated solvent, unless otherwise stated. 13C NMR spectra
are reported in (ppm) relative to deuterated chloroform (77.2 ppm)
unless otherwise stated, and all were obtained with 1H decoupling.
High-resolution mass spectra are recorded on a Shimadzu LCMS-IT-
TOF instrument in the ESI mode.
Scheme 3. Control experiments.
experimental results is proposed.
4.2. Procedure for synthesis of diselenides
4. Experimental section
[25] Diselenides were prepared according to literature methods.
To a stirred solution of selenium powder (10.0 mmol) and aryl
iodine (4.0 mmol) in DMSO (10.0 mL) was added CuO nanoparticles
(10.0 mol %) followed by KOH (2.5 equiv) under nitrogen atmo-
sphere at 90 ꢁC. The progress of the reaction was monitored by TLC.
After the reaction was complete, it was quenched with saturated
brine. The mixture was extracted with n-hexane for three times.
The combined organic layer was washed with water for three times,
and dried over anhydrous MgSO4. The dried solution was
condensed on a rotary evaporator to give pure diaryl diselenide.
4.1. General information
All reactions were carried out in dry test tubes sealed with
rubber caps. The test tube used was dried in an electric oven at
110 ꢁC. Chemicals were purchased from Aladdin, Adamas, Aldrich,
Alfa Aesar, and Kelong Chemical Co. and used as received, unless
other mentioned. Petroleum ether refers to the fraction boiling in
the 60e90 ꢁC range. Unless otherwise stated, there is no further
4

C. Xu, Z. He, H. Yang et al.
Tetrahedron xxx (xxxx) xxx
4.3. Procedure for synthesis of compound 4
CDCl3)
d
¼ 7.39 (dt, J ¼ 5.1, 3.0, 2H), 7.23e7.10 (m, 8H), 6.59 (s, 1H),
6.41 (s, 1H), 4.60 (t, J ¼ 8.1, 1H), 3.78 (s, 3H), 3.66 (d, J ¼ 10.2, 6H),
To a 25 mL glass test tube equipped a stir bar were added
(substituted) styrene 1 (0.5 mmol), (substituted) electron-rich ar-
ene 2 (0.60 mmol), diaryl diselenide 3 (0.5 mmol), FeCl3 (0.1 mmol)
and MeCN (4.0 mL). To avoid evaporation of the solvent, the system
was then fastened with a rubber septum under air atmosphere. The
test tube was stirred in an oil bath preheated at 80 ꢁC. After 12 h,
reaction progress was checked by TLC and confirmed reaction was
completed. After cooled to room temperature, the reaction mixture
was quenched by the addition of saturated NaCl solution (10 mL).
The reaction mixture was extracted with ethyl acetate (15 mL ꢂ 3).
The combined organic phase was dried over anhydrous MgSO4,
filtered and concentrated in vacuum on a rotary evaporator. The
resulting residue was purified by silica gel flash chromatography,
eluting with petroleum ether/EtOAc (20/1e5/1) to afford the cor-
responding products as a white/colorless/yellow/dark red viscous
liquid.
3.54e3.41 (m, 2H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 151.32,
148.31, 143.36, 142.89, 132.53, 131.07, 128.81, 128.23, 127.91, 126.57,
126.31, 123.51, 112.65, 97.94, 56.70, 56.34, 56.00, 44.24, 32.73;
HRMS (ESI): calculated for C23H24O3SeNa [M þ Na]þ ¼ 451.0791,
found 451.0783.
(2-(2,4-dimethoxyphenyl)-2-phenylethyl)(phenyl)selane
(4aca). [20] Yellow viscous liquid, 74% yield, 147 mg; 1H NMR
(400 MHz, CDCl3)
d
¼ 7.56e7.44 (m, 2H), 7.32e7.21 (m, 8H),
7.11e7.02 (m, 1H), 6.59e6.31 (m, 2H), 4.77e4.62 (m, 1H), 3.82e3.75
(m, 6H), 3.66e3.50 (m, 2H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 159.44, 157.82, 143.42, 132.40, 131.18, 128.81, 128.34, 128.19,
128.04, 126.49, 126.24, 124.46, 103.91, 98.66, 55.24, 55.17, 44.02,
32.73; HRMS (ESI): calculated for C22H23O2Se [M þ H]þ ¼ 399.0860,
found 399.0858.
(2-(3,4-dimethoxyphenyl)-2-phenylethyl)(phenyl)selane
(4ada). Yellow viscous liquid, 54% yield, 107 m; 1H NMR (400 MHz,
CDCl3)
d
¼ 7.53e7.43 (m, 2H), 7.33e7.30 (m, 2H), 7.29e7.23 (m, 6H),
4.4. Gram-scale aryl-arylselenization of alkenes
6.86e6.81 (m, 2H), 6.73 (s, 1H), 4.25 (t, J ¼ 8.0, 1H), 3.88e3.83 (m,
6H), 3.62e3.56 (m, 2H); 13C NMR (75 MHz, Chloroform-d)
To a 100 mL glass flask equipped a stir bar were added the
corresponding styrene 1a (5.0 mmol, 0.52g), Aryl-H 2a (6.0 mmol,
1.01g), diselenide 3a (5.0 mmol, 1.57g), FeCl3(0.1 mmol) and MeCN
(30.0 mL). To avoid evaporation of the solvent, the system was then
closed with a rubber septum under air atmosphere. The test tube
was stirred in an oil bath preheated at 80 ꢁC. After 12 h, reaction
progress was checked by TLC and confirmed reaction was
completed. After cooled to room temperature, the reaction mixture
was quenched by the addition of saturated NaCl solution (40 mL).
The reaction mixture was extracted with ethyl acetate (30 mL ꢂ 3).
The combined organic phase was dried over MgSO4, filtered and
concentrated in vacuum on a rotary evaporator. The resulting res-
idue was purified by silica gel flash chromatography, eluting with
petroleum ether/EtOAc ¼ 20/1 to afford the corresponding prod-
ucts as a yellow viscous liquid (4aaa).
d
¼ 148.81, 147.71, 143.77, 135.94, 132.63, 128.97, 128.47, 127.60,
126.80, 126.59, 119.58, 111.31, 111.02, 55.76, 51.12, 33.90; HRMS
(ESI): calculated for C22H22O2SeNa [M þ Na]þ ¼ 421.0683, found
421.0677.
(2-(4-methoxy-2,6-dimethylphenyl)-2-phenylethyl)(phenyl)
selane (4aea). Colorless oily liquid, 72% yield, 142 mg; 1H NMR
(400 MHz, CDCl3)
7.08e7.03 (m, 1H), 6.49 (d, J ¼ 11.9, 1H), 6.43 (s, 1H), 4.55 (t, J ¼ 7.8,
1H), 3.81 (dd, J ¼ 11.7, 9.0, 1H), 3.69 (dd, J ¼ 11.7, 7.2, 1H), 3.53 (s,
3H), 2.19 (s, 3H), 2.10 (s, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 7.40e7.31 (m, 2H), 7.20e7.10 (m, 7H),
d
¼ 158.17, 143.58, 137.69, 137.20, 132.54, 131.07, 128.84, 127.89,
127.73, 126.49, 125.76, 124.06, 110.61, 55.12, 44.11, 31.58, 21.32,
20.71; HRMS (ESI): calculated for C23H25OSe [M þ H]þ ¼ 397.1077,
found 397.1065.
phenyl(2-phenyl-2-(2,3,4-trimethoxy-6-methylphenyl)ethyl)
selane (4afa). White viscous liquid, 80% yield, 176 mg; 1H NMR
4.5. Procedure for synthesis of compound 5aa
(300 MHz, CDCl3)
d
¼ 7.50 (dd, J ¼ 6.4, 3.1, 2H), 7.30 (d, J ¼ 4.3, 4H),
7.22 (ddd, J ¼ 13.0, 6.7, 3.0, 4H), 4.64 (t, J ¼ 7.7, 1H), 3.94e3.85 (m,
To a 25 mL glass test tube equipped a stir bar were added the
corresponding styrene Aryl-H 2a (0.5 mmol), diselenide 3a
(0.5 mmol), FeCl3 (0.1 mmol) and MeCN (4.0 mL). To avoid evapo-
ration of the solvent, the system was then closed with a rubber
septum under air atmosphere. The test tube was stirred in an oil
bath preheated at 80 ꢁC. After 12 h, reaction progress was checked
by TLC and confirmed reaction was completed. After cooled to room
temperature, the reaction mixture was quenched by the addition of
saturated NaCl solution (10 mL). The reaction mixture was extrac-
ted with ethyl acetate (15 mL ꢂ 3). The combined organic phase
was dried over MgSO4, filtered and concentrated in vacuum on a
rotary evaporator. The resulting residue was purified by silica gel
flash chromatography, eluting with petroleum ether/EtOAc ¼ 10/1
to afford the corresponding products as a yellow viscous liquid
(5aa).
4H), 3.82e3.75 (m, 4H), 3.38 (s, 3H), 2.26 (s, 3H); 13C NMR (75 MHz,
Chloroform-d)
d
¼ 152.55, 151.83, 143.81, 140.58, 132.50, 131.84,
131.06, 128.88, 128.23, 127.94, 127.48, 126.58, 125.73, 109.10, 60.40,
59.84, 55.68, 43.77, 31.23, 20.94; HRMS (ESI): calculated for
C
24H25O3SeNa [M þ Na]þ ¼ 465.0946, found 465.0939.
3,4,5-trimethoxy-2-(1-phenyl-2-(phenylselanyl)ethyl)phenol
(4aga). Dark red viscous liquid, 84% yield, 175 mg; 1H NMR
(400 MHz, DMSO‑d6)
d
¼ 9.42 (s, 1H), 7.49e7.44 (m, 2H), 7.39e7.34
(m, 2H), 7.29e7.20 (m, 5H), 7.16e7.11 (m, 1H), 6.30 (s, 1H),
4.78e4.72 (m, 1H), 3.92 (dd, J ¼ 11.4, 9.2, 1H), 3.77 (dd, J ¼ 11.4, 7.3,
1H), 3.72 (s, 3H), 3.63 (s, 3H), 3.54 (s, 3H); 13C NMR (101 MHz,
Chloroform-d)
d
¼ 152.67, 152.49, 150.30, 143.46, 136.25, 132.57,
131.03, 128.97, 128.36, 127.81, 126.69, 126.31, 116.11, 96.84, 60.86,
60.73, 55.77, 41.22, 31.15; HRMS (ESI): calculated for C23H24O4SeNa
[M þ Na]þ ¼ 467.0734, found 467.0733.
phenyl(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)selane
3-(1-phenyl-2-(phenylselanyl)ethyl)-1H-indole (4 aha). Yellow
viscous liquid, 81% yield,152 mg; 1H NMR (400 MHz, Chloroform-d)
(4aaa). [20] Yellow viscous liquid, 88% yield, 188 mg; 1H NMR
(400 MHz, CDCl3)
d
¼ 7.41e7.32 (m, 2H), 7.24 (d, J ¼ 7.3, 2H),
d
¼ 7.96 (s, 1H), 7.65e7.57 (m, 2H), 7.50 (dd, J ¼ 8.0, 1.1, 1H),
7.18e7.09 (m, 5H), 7.08e7.01 (m, 1H), 6.01 (s, 2H), 4.85 (dd, J ¼ 9.5,
7.46e7.25 (m, 10H), 7.15 (ddd, J ¼ 8.0, 6.9, 1.1, 1H), 7.06 (d, J ¼ 2.4,
1H), 4.69 (t, J ¼ 7.8, 1H), 3.87 (dd, J ¼ 11.7, 7.5, 1H), 3.65 (dd, J ¼ 11.8,
7.1,1H), 3.84e3.78 (m,1H), 3.70 (s, 3H), 3.67e3.59 (m, 7H); 13C NMR
(75 MHz, Chloroform-d)
d
¼ 159.88, 159.17, 144.24, 132.52, 131.37,
8.1, 1H). 13C NMR (101 MHz, Chloroform-d)
d
¼ 143.91, 136.56,
128.66, 127.83, 127.74, 126.28, 125.62, 112.40, 91.13, 55.58, 55.14,
40.18, 31.48; HRMS (ESI): calculated for C23H24O3SeNa [M þ
Na]þ ¼ 451.0787, found 451.0783.
132.82, 131.27, 129.22, 128.62, 128.03, 126.98, 126.81, 126.79, 122.29,
121.74, 119.58, 119.39, 118.86, 111.38, 43.68, 34.46; HRMS (ESI):
calculated for C22H19NSeNa [M þ Na]þ ¼ 400.0575, found 400.0577.
phenyl(2-(p-tolyl)-2-(2,4,6-trimethoxyphenyl)ethyl)selane
phenyl(2-phenyl-2-(2,4,5-trimethoxyphenyl)ethyl)selane
(4aba). Yellow viscous liquid, 84% yield,180 mg; 1H NMR (400 MHz,
(4baa). Yellow viscous liquid, 56% yield,123 mg; 1H NMR (400 MHz,
5

C. Xu, Z. He, H. Yang et al.
Tetrahedron xxx (xxxx) xxx
CDCl3)
d
¼ 7.53e7.40 (m, 2H), 7.27e7.10 (m, 6H), 7.05e6.95 (m, 1H),
(2-(4-fluorophenyl)-2-(4-methoxy-2,6-dimethylphenyl)ethyl)(-
phenyl)selane (4fda). Colorless oily liquid, 56% yield, 115 mg; 1H
6.15e6.07 (m, 2H), 4.92 (dd, J ¼ 9.7, 7.0, 1H), 3.93e3.87 (m, 1H),
3.84e3.80 (m, 3H), 3.78e3.66 (m, 7H), 2.32e2.29 (m, 3H); 13C NMR
NMR (400 MHz, CDCl3)
d
¼ 7.40e7.31 (m, 2H), 7.18e7.10 (m, 5H),
(75 MHz, Chloroform-d)
d
¼ 159.82, 159.21, 144.12, 137.12, 132.49,
6.88e6.79 (m, 2H), 6.55e6.49 (m, 1H), 6.43 (s, 1H), 4.49 (t, J ¼ 7.5,
128.65, 127.62, 126.45, 126.24, 124.83, 112.36, 91.14, 55.60, 55.14,
40.13, 31.60, 21.53; HRMS (ESI): calculated for C24H27O3Se [M þ
H]þ ¼ 443.1120, found 443.1120.
1H), 3.75 (dd, J ¼ 11.8, 8.5, 1H), 3.69e3.61 (m, 1H), 3.55 (s, 3H), 2.20
(s, 3H), 2.09 (s, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 160.99 (d,
J ¼ 243.8), 157.97, 139.15 (d, J ¼ 2.9), 137.40, 137.26, 132.61, 130.78,
129.19, 129.09, 128.82, 126.54, 124.04, 114.63, 114.35, 110.56, 54.96,
43.51, 31.54, 21.24, 20.59; HRMS (ESI): calculated for C23H23FNaOSe
[M þ Na]þ ¼ 437.0788, found 437.0791.
(2-(4-(tert-butyl)phenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)(-
phenyl)selane (4caa). Yellow viscous liquid, 51% yield, 123 mg; 1H
NMR (400 MHz, Chloroform-d)
d
¼ 7.47e7.28 (m, 2H), 7.23e7.01
(m, 8H), 6.01 (s, 2H), 4.82 (dd, J ¼ 10.0, 6.7, 1H), 3.85 (dd, J ¼ 11.4,
(2-(4-chlorophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)(phenyl)
selane (4gaa). [20] Yellow viscous liquid, 87% yield, 200 mg; 1H
10.0, 1H), 3.68 (s, 3H), 3.63e3.53 (m, 4H), 1.19 (s, 9H); 13C NMR
(101 MHz, Chloroform-d)
d
¼ 159.87, 159.32, 148.32, 141.28, 132.62,
NMR (400 MHz, CDCl3)
6.01 (s, 2H), 4.84e4.75 (m, 1H), 3.70 (d, J ¼ 4.6, 4H), 3.64e3.58 (m,
7H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 7.38e7.32 (m, 2H), 7.18e7.08 (m, 7H),
131.52, 128.71, 127.50, 126.31, 124.77, 112.40, 91.20, 55.68, 55.22,
39.98, 34.31, 31.94, 31.43; HRMS (ESI): calculated for C27H32O3SeNa
[M þ Na]þ ¼ 507.1411, found 507.1411.
d
¼ 160.04, 158.99, 142.68,
132.61, 131.20, 131.07, 129.27, 128.71, 127.77, 126.42, 112.01, 91.08,
(2-([1,10-biphenyl]-4-yl)-2-(2,4,6-trimethoxyphenyl)ethyl)(-
phenyl)selane (4daa). Yellow viscous liquid, 47% yield, 118 mg; 1H
55.56, 55.16, 39.62, 31.12. HRMS (ESI): calculated for C23H23ClO3
-
SeNa [M þ Na]þ ¼ 485.0390, found 485.0394.
(2-(4-chlorophenyl)-2-(2,4,5-trimethoxyphenyl)ethyl)(phenyl)
selane (4gba). Yellow viscous liquid, 76% yield, 175 mg; 1H NMR
NMR (400 MHz, Chloroform-d)
d
¼ 7.47e7.42 (m, 2H), 7.39e7.33
(m, 4H), 7.32e7.26 (m, 4H), 7.20e7.15 (m, 1H), 7.12e7.05 (m, 3H),
6.00 (s, 2H), 4.88 (dd, J ¼ 9.5, 7.1, 1H), 3.82 (dd, J ¼ 11.5, 9.5, 1H),
3.70e3.64 (m, 4H), 3.59 (s,3H); 13C NMR (75 MHz, Chloroform-d)
(300 MHz, CDCl3)
d
¼ 7.52e7.45 (m, 2H), 7.29e7.19 (m, 7H), 6.68 (s,
1H), 6.51 (s, 1H), 4.65 (t, J ¼ 8.0, 1H), 3.88 (s, 3H), 3.76 (d, J ¼ 16.3,
6H), 3.63e3.46 (m, 2H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 160.09, 159.31, 143.55, 141.29, 138.61, 132.71, 131.47, 128.85,
d
¼ 151.16, 148.43, 142.82, 141.83, 132.57, 131.83, 130.64, 129.24,
128.75, 128.42, 127.05, 126.98, 126.66, 126.48, 112.36, 91.28, 55.75,
55.29, 40.11, 31.62; HRMS (ESI): calculated for C29H28O3SeNa [M þ
Na]þ ¼ 527.1091, found 527.1096.
128.78, 128.21, 126.63, 122.86, 112.45, 97.78, 56.69, 56.13, 55.92,
43.75, 32.35; HRMS (ESI): calculated for C23H23ClO3SeNa [M þ
Na]þ ¼ 485.0388, found 485.0394.
phenyl(2-(4-(trifluoromethyl)phenyl)-2-(2,4,6-
(2-(4-chlorophenyl)-2-(2,3,4-trimethoxy-6-methylphenyl)eth-
yl)(phenyl)selane (4gca). White viscous liquid, 70% yield, 166 mg;
trimethoxyphenyl)ethyl)selane (4eaa). Yellow viscous liquid, 70%
yield, 173 mg; 1H NMR (400 MHz, CDCl3)
d
¼ 7.54e7.40 (m, 6H),
1H NMR (400 MHz, CDCl3)
d
¼ 7.43e7.34 (m, 2H), 7.18e7.10 (m, 7H),
7.28e7.21 (m, 3H), 6.12 (s, 2H), 4.99 (t, J ¼ 8.2, 1H), 3.90e3.80 (m,
4H), 3.79e3.70 (m, 7H); 13C NMR (75 MHz, Chloroform-d)
6.37 (s, 1H), 4.43 (s, 1H), 3.77e3.67 (m, 7H), 3.60 (dd, J ¼ 11.8, 8.1,
1H), 3.29 (d, J ¼ 18.2, 3H), 2.12 (s, 3H); 13C NMR (75 MHz,
d
¼ 160.18, 158.95, 148.31, 132.66, 130.86, 128.71, 128.16, 127.46,
Chloroform-d)
d
¼ 152.48, 152.06, 142.34, 140.62, 132.78, 131.74,
126.49, 124.58, 124.53, 111.58, 90.99, 55.45, 55.07, 40.07, 30.74;
HRMS (ESI): calculated for C24H24F3O3Se [M þ H]þ ¼ 497.0841,
found 497.0838.
131.48, 130.76, 129.00, 128.05, 127.73, 126.84, 124.24, 109.18, 60.49,
60.00, 55.76, 43.43, 31.16, 20.92; HRMS (ESI): calculated for
C
24H26ClO3Se [M þ H]þ ¼ 477.0735, found 477.0730.
(2-(4-fluorophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)(phenyl)
selane (4faa). [20] Yellow viscous liquid, 76% yield, 169 mg; 1H NMR
(2-(4-chlorophenyl)-2-(4-methoxy-2,6-dimethylphenyl)eth-
yl)(phenyl)selane (4gda). Colorless oily liquid, 67% yield, 144 mg;
(400 MHz, CDCl3)
d
¼ 7.47e7.40 (m, 2H), 7.30e7.19 (m, 5H),
1H NMR (400 MHz, CDCl3)
d
¼ 7.49e7.42 (m, 2H), 7.28e7.18 (m, 7H),
6.94e6.84 (m, 2H), 6.09 (s, 2H), 4.93e4.83 (m, 1H), 3.85e3.77 (m,
4H), 3.73e3.65 (m, 7H); 13C NMR (75 MHz, Chloroform-d)
6.62 (s, 1H), 6.52 (s, 1H), 4.58 (t, J ¼ 7.6, 1H), 3.86e3.73 (m, 2H), 3.64
(s, 3H), 2.30 (s, 3H), 2.19 (s, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 162.50, 159.87, 159.28, 158.88, 139.77, 132.45, 131.03, 129.25,
d
¼ 158.02, 142.06, 137.48, 132.73, 131.40, 130.75, 129.16, 128.90,
129.15, 128.62, 126.29, 114.41, 114.13, 112.08, 90.96, 55.42, 54.99,
127.92, 126.67, 126.58, 124.09, 110.60, 55.07, 43.62, 31.29, 21.31,
39.44, 31.33; HRMS (ESI): calculated for
C
23H24FO3Se [M
þ
H]þ ¼ 447.0856, found 447.0870.
20.65; HRMS (ESI): calculated for
C
23H23ClOSeNa [M
þ
Na]þ ¼ 453.0493, found 453.0495.
(2-(4-fluorophenyl)-2-(2,4,5-trimethoxyphenyl)ethyl)(phenyl)
selane (4fba). Yellow viscous liquid, 67% yield, 149 mg; 1H NMR
(2-(4-bromophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)(phenyl)
selane (4haa). [20] Yellow viscous liquid, 90% yield, 227 mg; 1H
(400 MHz, CDCl3)
d
¼ 7.47e7.32 (m, 2H), 7.15 (dddd, J ¼ 11.5, 8.4,
NMR (400 MHz, CDCl3)
d
¼ 7.42e7.30 (m, 2H), 7.30e7.20 (m, 2H),
5.6, 2.6, 5H), 6.94e6.83 (m, 2H), 6.56 (s, 1H), 6.41 (s, 1H), 4.55 (t,
J ¼ 8.1,1H), 3.79 (s, 3H), 3.67 (d, J ¼ 13.2, 6H), 3.52e3.36 (m, 2H); 13
C
7.14 (ddt, J ¼ 11.7, 9.5, 4.8, 5H), 6.00 (s, 2H), 4.84e4.71 (m, 1H),
3.75e3.68 (m, 4H), 3.66e3.57 (m, 7H); 13C NMR (75 MHz, CDCl3)
NMR (75 MHz, Chloroform-d)
d
¼ 162.94, 159.70, 151.20, 148.38,
d
¼ 160.03, 158.96, 143.20, 132.60, 131.03, 130.69, 129.68, 128.69,
142.84, 139.01, 132.61, 130.83, 129.38 (d, J ¼ 7.8), 128.86, 126.69,
126.41, 119.31, 111.90, 91.06, 55.53, 55.14, 39.67, 31.01; HRMS (ESI):
calculated for C23H24BrO3Se [M þ H]þ ¼ 507.0074, found 507.0069.
(2-(4-bromophenyl)-2-(2,4,5-trimethoxyphenyl)ethyl)(phenyl)
selane (4hba). Yellow viscous liquid, 85% yield, 215 mg; 1H NMR
123.24, 114.99 (d, J ¼ 21.1), 112.39, 97.79, 56.72, 56.26, 55.99, 43.65,
32.72; HRMS (ESI): calculated for
C
23H23FO3SeNa [M
þ
Na]þ ¼ 469.0673, found 469.0689.
(2-(4-fluorophenyl)-2-(2,3,4-trimethoxy-6-methylphenyl)eth-
yl)(phenyl)selane (4fca). White viscous liquid, 60% yield, 138 mg;
(400 MHz, CDCl3)
d
¼ 7.44e7.26 (m, 4H), 7.19e7.14 (m, 3H),
1H NMR (400 MHz, Chloroform-d)
d
¼ 7.42e7.33 (m, 2H), 7.15 (qd,
7.08e7.00 (m, 2H), 6.56 (s, 1H), 6.40 (s, 1H), 4.52 (t, J ¼ 8.1, 1H), 3.79
(s, 3H), 3.66 (d, J ¼ 18.5, 6H), 3.51e3.34 (m, 2H); 13C NMR (75 MHz,
J ¼ 5.1, 4.5, 2.5, 5H), 6.90e6.85 (m, 2H), 6.37 (s, 1H), 4.45 (t, J ¼ 6.9,
1H), 3.76e3.73 (m, 4H), 3.69 (s, 3H), 3.62 (dd, J ¼ 11.8, 8.2, 1H), 3.31
Chloroform-d)
d
¼ 151.23, 148.50, 142.87, 142.42, 132.68, 131.27,
(s, 3H), 2.13 (s, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 161.02 (d,
130.71, 129.72, 128.88, 126.75, 122.82, 120.09, 112.41, 97.77, 56.78,
56.24, 56.02, 43.90, 32.37; HRMS (ESI): calculated for C23H23BrO3
J ¼ 244.2), 152.45, 151.93, 140.57, 139.41, 132.65, 131.68, 130.79,
128.95, 128.29 (d, J ¼ 7.5), 127.92, 126.74, 114.66 (d, J ¼ 21.0), 109.10,
60.44, 59.94, 55.69, 43.28, 31.36, 20.90; HRMS (ESI): calculated for
-
SeNa [M þ Na]þ ¼ 528.9870, found 528.9888.
(2-(4-bromophenyl)-2-(2,3,4-trimethoxy-6-methylphenyl)eth-
yl)(phenyl)selane (4hca). White viscous liquid, 74% yield, 192 mg;
C
24H25FO3SeNa [M þ Na]þ ¼ 483.0858, found 483.0845.
1H NMR (400 MHz, CDCl3)
d
¼ 7.38e7.33 (m, 2H), 7.28 (d, J ¼ 8.5,
6

C. Xu, Z. He, H. Yang et al.
Tetrahedron xxx (xxxx) xxx
2H), 7.14e7.10 (m, 3H), 7.04 (d, J ¼ 8.3, 2H), 6.35 (s, 1H), 4.40 (s, 1H),
3.74e3.68 (m, 4H), 3.67 (s, 3H), 3.61e3.54 (m, 1H), 3.29 (s, 3H), 2.10
selane (4aag). Yellow viscous liquid, 82% yield, 207 mg; 1H NMR
(400 MHz, CDCl3)
d
¼ 7.36e7.22 (m, 8H), 7.15 (dd, J ¼ 8.1, 6.4, 1H),
(s, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 152.39,152.00,142.82,
6.11 (d, J ¼ 6.1, 2H), 4.94 (ddd, J ¼ 16.6, 9.7, 7.0, 1H), 3.94e3.85 (m,
140.52, 132.71, 131.67, 130.93, 130.67, 129.36, 128.95, 127.58, 126.78,
119.47, 109.09, 60.42, 59.93, 55.69, 43.41, 31.00, 20.88; HRMS (ESI):
calculated for C24H25BrO3SeNa [M þ Na]þ ¼ 543.0035, found
543.0045.
1H), 3.84e3.78 (m, 3H), 3.78e3.67 (m, 7H); 13C NMR (75 MHz,
Chloroform-d)
d
¼ 159.88, 159.02, 143.96, 134.16, 131.73, 131.56,
130.09, 127.73, 125.65, 120.35, 111.95, 90.94, 55.48, 55.08, 40.09,
31.61; HRMS (ESI): calculated for
C
23H24BrO3Se [M
þ
(2-(4-bromophenyl)-2-(4-methoxy-2,6-dimethylphenyl)eth-
yl)(phenyl)selane (4hda). Colorless oily liquid, 68% yield, 161 mg;
H]þ ¼ 507.0072, found 507.0069.
(2-chlorophenyl)(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)
1H NMR (400 MHz, CDCl3)
d
¼ 7.38e7.31 (m, 2H), 7.29e7.22 (m,
selane (4aah). Yellow viscous liquid, 78% yield, 180 mg; 1H NMR
(400 MHz, CDCl3)
¼ 7.43e7.12 (m, 9H), 6.13 (s, 2H), 5.01 (dt,
J ¼ 15.8, 7.9, 1H), 3.94 (ddd, J ¼ 11.0, 9.4, 5.4, 1H), 3.84e3.72 (m,
10H); 13C NMR (75 MHz, Chloroform-d)
2H), 7.18e7.12 (m, 3H), 7.06 (d, J ¼ 8.3, 2H), 6.53e6.39 (m, 2H), 4.45
(d, J ¼ 6.9, 1H), 3.75e3.62 (m, 2H), 3.53 (s, 3H), 2.19 (s, 3H), 2.08 (s,
d
3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 158.11, 142.70, 137.59,
d
¼ 159.95, 159.11, 144.02,
132.85, 130.98, 130.85, 129.69, 129.01, 126.79, 126.61, 124.20, 119.63,
110.70, 55.17, 43.90e43.67 (m), 31.31, 21.44, 20.78; HRMS (ESI):
calculated for C23H23BrOSeNa [M þ Na]þ ¼ 496.9985, found
496.9990.
133.68 (d, J ¼ 197.2), 131.08, 129.16, 127.79, 127.41, 126.84, 126.71,
125.72, 112.07, 91.09, 55.58, 55.14, 39.59, 29.99; HRMS (ESI):
calculated for C23H23ClNaO3Se [M þ Na]þ ¼ 485.0390, found
485.0394.
(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)(p-tolyl)selane
(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)(m-tolyl)selane
(4aab). Yellow viscous liquid, 82% yield,181 mg; 1H NMR (400 MHz,
(4aai). Yellow viscous liquid, 71% yield, 156 mg; 1H NMR (400 MHz,
CDCl3)
d
¼ 7.28e7.11 (m, 6H), 7.07e7.01 (m, 1H), 6.99e6.90 (m, 2H),
CDCl3)
d
¼ 7.35 (t, J ¼ 6.3, 2H), 7.30e7.22 (m, 4H), 7.18e7.10 (m, 2H),
6.01 (d, J ¼ 6.6, 2H), 4.91e4.75 (m, 1H), 3.81e3.74 (m, 1H),
7.03 (d, J ¼ 7.5, 1H), 6.12 (d, J ¼ 5.6, 2H), 4.97 (dt, J ¼ 18.4, 9.2, 1H),
3.94e3.89 (m, 1H), 3.81 (d, J ¼ 5.3, 3H), 3.77e3.71 (m, 7H), 2.34 (d,
3.72e3.69 (m, 3H), 3.65e3.56 (m, 7H), 2.27e2.19 (m, 3H); 13C NMR
(75 MHz, Chloroform-d)
d
¼ 159.76, 159.05, 144.23, 136.14, 132.93,
J ¼ 7.9, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 159.80, 159.10,
129.40, 127.74, 127.63, 127.31, 125.49, 112.29, 90.98, 55.45, 55.00,
40.12, 31.77, 20.92; HRMS (ESI): calculated for C24H27O3Se [M þ
H]þ ¼ 443.1116, found 443.1120.
144.23, 138.25, 133.16, 131.05, 129.49, 128.42, 127.80, 127.68, 127.11,
125.56, 112.32, 91.01, 55.52, 55.06, 40.23, 31.36, 21.17; HRMS (ESI):
calculated for C24H27O3Se [M þ H]þ ¼ 443.1106, found 443.1120.
phenyl(2,4,6-trimethoxyphenyl)selane (5aa). [26] Yellow
viscous liquid, 54% yield, 87 mg; 1H NMR (400 MHz, Chloroform-d)
(4-methoxyphenyl)(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)
selane (4aac). Yellow viscous liquid, 69% yield, 158 mg; 1H NMR
(400 MHz, CDCl3)
d
¼ 7.38e7.26 (m, 2H), 7.22 (d, J ¼ 7.4, 2H), 7.13
d
¼ 7.19e6.97 (m, 5H), 6.13 (s, 2H), 3.78 (s, 3H), 3.70 (s, 6H); 13C
(dd, J ¼ 10.3, 4.8, 2H), 7.03 (t, J ¼ 7.2, 1H), 6.74e6.64 (m, 2H), 6.01 (s,
NMR (101 MHz, Chloroform-d)
d
¼ 163.00, 161.95, 133.61, 128.83,
2H), 4.87e4.72 (m, 1H), 3.78e3.68 (m, 7H), 3.65e3.59 (m, 6H), 3.52
128.70, 125.28, 97.22, 91.21, 56.31, 55.42; HRMS (ESI): calculated for
(dt, J ¼ 11.9, 5.9, 1H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 159.76,
C
15H17O3Se [M þ H]þ ¼ 325.0336, found 325.0338.
159.09, 158.84, 144.31, 135.44, 127.78, 127.66, 125.51, 120.91, 114.30,
112.31, 91.00, 55.49, 55.12, 55.06, 40.25, 32.60; HRMS (ESI): calcu-
lated for C24H27O4Se [M þ H]þ ¼ 459.1076, found 459.1070.
(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)(4-(tri-
Declaration of competing interest
The authors declare that they have no known competing
financial interests or personal relationships that could have
appeared to influence the work reported in this paper.
fluoromethyl)phenyl)selane (4aad). Yellow viscous liquid, 75%
yield, 186 mg; 1H NMR (400 MHz, Chloroform-d)
d
¼ 7.43e7.30 (m,
4H), 7.24 (dd, J ¼ 8.0, 1.4, 2H), 7.14 (t, J ¼ 7.6, 2H), 7.09e7.02 (m, 1H),
5.99 (s, 2H), 4.85 (dd, J ¼ 9.6, 7.0, 1H), 3.85 (dd, J ¼ 11.6, 9.6, 1H),
3.70e3.65 (m, 4H), 3.60 (s, 6H); 13C NMR (75 MHz, Chloroform-d)
Acknowledgment
d
¼ 160.00, 159.04, 143.84, 137.01, 131.46, 129.86, 127.78, 127.73,
This work was financially supported by the National Natural
Science Foundation of China (No. 21372034) and the State Key
Laboratory of Geohazard Prevention and Geoenvironment Protec-
tion (No. SKLGP2020Z003).
125.75, 125.18 (q, J ¼ 3.9), 122.42, 111.85, 90.95, 55.43, 55.00, 39.97,
30.90; HRMS (ESI): calculated for
C
24H24F3O3Se [M
þ
H]þ ¼ 497.0838, found 497.0838.
(4-fluorophenyl)(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)
selane (4aae). Yellow viscous liquid, 70% yield, 156 mg; 1H NMR
(400 MHz, CDCl3)
Appendix A. Supplementary data
d
¼ 7.39e7.27 (m, 2H), 7.22 (d, J ¼ 7.2, 2H),
7.16e7.12 (m, 2H), 7.05 (ddd, J ¼ 7.2, 5.9, 1.2, 1H), 6.89e6.78 (m, 2H),
6.01 (d, J ¼ 4.8, 2H), 4.80 (dd, J ¼ 9.7, 7.0, 1H), 3.80e3.74 (m, 1H),
3.70 (d, J ¼ 4.1, 3H), 3.63e3.54 (m, 7H); 13C NMR (75 MHz,
Supplementary data to this article can be found online at
https://doi.org/10.1016/j.tet.2021.132239.
Chloroform-d)
d
¼ 161.99 (d, J ¼ 245.9), 159.86, 159.07, 144.11,
References
135.28, 135.18, 127.76, 127.72, 125.62, 125.37 (d, J ¼ 3.3), 115.79,
115.51, 112.10, 91.00, 55.48, 55.07, 40.21, 32.32. HRMS (ESI): calcu-
lated for C23H23FO3SeK [M þ K]þ ¼ 485.0452, found 485.0429.
(4-chlorophenyl)(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)
selane (4aaf). Yellow viscous liquid, 76% yield, 175 mg; 1H NMR
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M. Iwaoka, Chembiochem 19 (2018) 207;
(400 MHz, CDCl3)
d
¼ 7.25 (ddd, J ¼ 16.6, 9.2, 4.9, 4H), 7.17e7.04 (m,
(b) T. Wirth, Angew. Chem. 127 (2015) 10212;
5H), 6.01 (d, J ¼ 5.7, 2H), 4.81 (dd, J ¼ 9.6, 7.0, 1H), 3.82e3.76 (m,
1H), 3.70 (d, J ¼ 4.6, 3H), 3.64e3.58 (m, 7H); 13C NMR (75 MHz,
(c) W.W.D. Mont, Angew. Chem. Int. Ed. 27 (1988) 444.
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Lett. 21 (2019) 885.
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(b) F.V. Singh, T. Wirth, Catal. Sci. & Tech. 9 (2019) 1073.
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Chloroform-d)
d
¼ 159.89, 159.03, 143.99, 133.96, 132.35, 129.35,
128.65, 127.73, 125.65, 111.99, 90.97, 55.47, 55.07, 40.12, 31.73;
HRMS (ESI): calculated for C23H23ClO3SeK [M þ K]þ ¼ 501.0127,
found 501.0133.
(4-bromophenyl)(2-phenyl-2-(2,4,6-trimethoxyphenyl)ethyl)
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C. Xu, Z. He, H. Yang et al.
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