Electrochemical Difunctionalization of Olefines: Access to Selenomethyl-Substituted Cyclic Ethers or Lactones

Article abstract of DOI:10.1002/adsc.201901115

A metal- and oxidant-free electrochemical method for preparing selenomethyl-substituted cyclic ethers or lactones via difunctionalization of olefines is presented. A series of selenomethyl-substituted cyclic ethers, particularly 9- and 11- membered, selen

Full text of DOI:10.1002/adsc.201901115

Title: Electrochemical Difunctionalization of Olefines: Access to
Selenomethyl-Substituted Cyclic Ethers or Lactones
Authors: Xiu-Jin Meng, Ping-Fu Zhong, Yu-Mei Wang, Heng-shan
Wang, Hai-Tao Tang, and Ying-ming Pan
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Advanced Synthesis & Catalysis
10.1002/adsc.201901115
COMMUNICATION
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Electrochemical Difunctionalization of Olefines: Access to Selen
omethyl-Substituted Cyclic Ethers or Lactones
a,c
a,c
a
,a
,a
Xiu-Jin Meng, Ping-Fu Zhong, Yu-Mei Wang, Heng-Shan Wang,* Hai-Tao Tang,* and Ying-
Ming Pan*
,
a,b
a
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry
and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People’s Republic of China. E-
mail: hshwang@mailbox.gxnu.edu.cn；httang@gxnu.edu.cn; panym@mailbox.gxnu.edu.cn
b
Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, Yulin Normal University,
Yuilin 537000, People’s Republic of China.
cThese authors contributed equally to this work
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract. A metal- and oxidant-free electrochemical
method for preparing selenomethyl-substituted cyclic
ethers or lactones via difunctionalization of olefines is
presented. A series of selenomethyl-substituted cyclic
ethers, particularly 9- and 11- membered, selenomethyl-
substituted lactones (4–6 membered), and selenomethyl-
substituted phthalides can be obtained via this reaction.
This method features convenient operation, an electron
as oxidant, and ammonium iodide as electrolyte, thereby
making it a green synthesis method.
direct construction of C-O bond within
[8]
corresponding acids or alcohols
. In 2005, Togo
and coworker reported the photochemical
preparation of 2-substituted 1,3-dioxane and
tetrahydrofuran from alcohols with polymer-
supported hypervalent iodine reagent in the
[
9]
presence of I2 (Scheme 1b). Over the past
decade, the syntheses of these molecules have
been extensively investigated, and significant
achievements, have been reached. However,
shortcomings, such as: harsh reaction conditions,
multistep reactions , and formation of undesired
by-products, are ubiquitous in most routes.
Therefore, developing new tactics is desirable.
Organoselenium compounds have been
extensively studied given their wide application
to drug design, functional organic materials, food
chemistry, and molecular probes.[ Given the
importance of organoselenium compounds,
introducing selenium to organic compounds has
attracted considerable attention. Recently, our
Keywords: electrochemistry, difunctionalization of
olefines, cyclic ethers, lactones, phthalides
Cyclic ethers and lactones are the two most
common structural units in nature and exist widely
in the areas of agrochemicals, pharmaceuticals, and
polymer materials.[
1]
For example, Zoapatanol
(
Figure 1), a natural diterpenoid oxepane, is isolated
10]
from the leaves of a Mexican zoapatle plant, namely,
Montanoa tomentosa and is found to display
antifertility activity.[ Normally, lactones are
known for their fruity aroma. For example,
tetrahydro-6-pentyl-2H-pyran-2-one (DDL),[ is a
2]
group has reported
decarboxylative/click
a
copper-catalyzed
3]
cascade reaction to
type of decalactone that is naturally found in fruits, construct selenium-containing triazole comp-
such as coconut and milk products, and has a large
market demand, given its application to flavor pest
control, and as food additive. In addition, a
series of lactones, such as -lactones, and δ-
lactones, is extensively used in cosmetic
fragrance and flavor considering their own
ounds. Three of the 5-selanyl-1,2,3-triazoles have
,
[
4]
[5]

characteristic odors (Figure 1).[ Accordingly,
6]
a
various of synthetic routes have been developed
to construct these scaffolds. The attractive methods
for the synthesizing of these skeletons are ring
Figure 1. Bioactive molecules containing a cyclic ether
moiety and food additives containing a lactone moiety.
[
7]
closing metathesis (RCM) (Scheme 1a) and
1
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Advanced Synthesis & Catalysis
10.1002/adsc.201901115
We selected pent-4-en-1-ol (1a) and diphenyl
diselenide (2a) as model substrates for optimizing
reaction conditions (Table 1). Electrolysis was
conducted in an undivided cell equipped with a
reticulated vitreous carbon (RVC) cathode and a
platinum anode. The optimal yield of 3-(phenyl-
selanyl) tetrahydro-2H-pyran (3a) (98%) was
obtained when constant current of 10 mA and 5
mol% NH
electrocatalyst. Control experiments showed that the
reaction was completely abolished when NH Br or
NH Cl (Entries 2 and 3) was chosen as the electrolyte
4
I were used as the electrolyte and
4
4
or when dichloroethane (Entry 9) was adopted as the
solvent or when no electric current (Entry 11) was
used. Selecting KI as the electrolyte (Entry 5), using
another solvent (e.g., MeOH [entry 8]), and
exchanging electrode (Entry 14) were found to be
minimally efficient in this reaction. However, using
another electrolyte (e.g., TBAI [Entry 4]), using
another solvent (e.g., DMF or DMSO [Entries 6 and
Scheme 1. Synthesis of O-containing heterocycles
7
]), choosing Pt plate or RVC (Entries 12 and 13) as
been found to display potent inhibitory activities
against MGC-803 cell lines, and one kind of 5-
selanyl-1,2,3-triazoles is found to be cytotoxic
electrode significantly decreased product (3a) yield.
Table 1. Optimization of reaction conditions.
a, b
[
11]
agents to T-24 cell lines
.
Inspired by these
reports, we suspect that introducing selenium to
lactones and cyclic ethers is of significant interest in
the pharmaceutical industry and academic research
Yield
Entry
Deviation from standard conditions
None
(%)b
(
Scheme 1d).
Currently, the difunctionalization of alkenes is a
1
2
3
4
5
6
7
8
9
98%
NR c
NH
NH
4
Br as the electrolyte
Cl as the electrolyte
powerful and straightforward method for synthetizing
various biologically active compounds and natural
products.[ Generally, this process mainly focuses
4
NR
39%
75%
54%
62%
88%
NR
trace
NR
45%
36%
82%
TBAI as the electrolyte
KI as the electrolyte
DMF as the solvent
DMSO as the solvent
12]
[13]
[14]
on transition metal catalysis (including Pd, Ni,
Cu,[
metal-free
15]
[16]
[17]
Au, , Fe , and others[20]),
[18]
[19]
CH
3
OH as the solvent
Ag,
Re,
catalysis
CH ClCH
3
3
Cl as the solvent
(but
requires
[over-]
and
1
0
1,4-Dioxane as the solvent
no electricity
Pt plate (1 cm × 1 cm) as the anode and cathode
RVC (1 cm × 1 cm) as the anode and cathode
RVC (1 cm × 1 cm) as the anode, Pt plate (1 cm × 1
cm) as the cathode
[21]
stoichiometric amount of oxidants),
11
12
photocatalysis.[
22]
In recent years, electrochemical
1
3
synthesis has attracted considerable attention in
synthetic organic chemistry considering its utilization
of electrons as “reagents” to accomplish the redox
14
aReaction conditions: undivided cell with Pt plate anode
(1 cm × 1 cm) and reticulated vitreous carbon (RVC)
cathode (100 PPI, 1 cm × 1 cm × 1.2 cm), constant current
process; this process is a powerful tool for
synthesizing organic compounds.[
23]
Xu’s group
successfully realized the difunctionalization of
alkenes via electrochemical synthesis in a simple and
moderate condition to construct saturated O-
heterocycles (Scheme 1c).[24] Although there were
some tactics for the construction of selenomethyl-
substituted ether/lactone products in the previous
=
10 mA, 1a (0.5 mmol), 2a (0.25 mmol), NH
4
I (5 mol%),
and solvent (6 mL) under air atmosphere at room
temperature for 6 h. Isolated yields. NR = no reaction.
b
c
We explored the scope of the substrate with
optimized conditions by first varying the olefinic
alcohols (1) of different lengths (Scheme 2). The
reaction showed broad compatibility with various
olefinic alcohols, and the corresponding products 5–
[25]
reports, the oxidants were essential (Scheme 1d).
Given our consistent and continuous interest in
synthesizing functionalized heterocycles via
electrochemical synthesis,[
we reported an
26]
7
-, 9-, and 11-membered ring selenomethyl-
electrochemical method for preparing selenomethyl-
substituted cyclic ethers and lactones via
difunctionalization of olefines.
substituted ethers were obtained in good to excellent
yields (3a–3e) (Scheme 2). We then subjected
various selenides to proceed to selenylation with
2
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Advanced Synthesis & Catalysis
10.1002/adsc.201901115
pent-4-en-1-ol 1a (Scheme 2). When the para which obtained from pent-1-en-3-ol, was
position of phenyl selenide was replaced with confirmed via X-ray analysis. However, when
alkyl (ethyl) electron-withdrawing group (Br or CH
CF ), the reaction generated the expected obtained other ring opening products with R =
products (3f 3h, and 3i) in good to excellent methoxyl groups (3l′–3n′).
3
OH was chosen as solvent unexpectedly, we
3
,
yields, and the structure of 3i was confirmed via
X-ray analysis. [ Furthermore, when the meta
position of phenyl selenide was replaced with -F,
the target product 3g was obtained in a
satisfactory yield. Notably, benzyl selenide can
also undergo this reaction smoothly and deliver the
final product 3j in excellent yield.
Given that olefinic acids and enols had double
bonds and OH groups, we speculated that olefinic
acids may also occur in the abovementioned reaction.
Therefore, we tested various olefinic carboxylic acids
(Scheme 4). Moreover, a series of olefinic carboxylic
acids was also well tolerated under the optimal
conditions and resulted in the desired products 4- to
27]
6- membered ring selenomethyl-substituted lactones
in good to excellent yields (5a–5d).
Scheme 2. Substrate scope of olefinic alcohols and
selenides. Reaction conditions: Undivided cell with Pt plate
as the anode (1 cm × 1 cm) and reticulated vitreous carbon
Scheme 4. Substrate scope of olefinic acids and selenides.
Reaction conditions: Undivided cell with Pt plate as the
anode (1 cm × 1 cm) and reticulated vitreous carbon
(
RVC) as the cathode (100 PPI, 1 cm × 1 cm × 1.2 cm),
constant current = 10 mA, 1 (0.5 mmol), 2 (0.25 mmol),
catalyst (5 mol%), and solvent (6 mL) under atmospheric
air at room temperature for 6 h. Isolated yields.
(
RVC) as the cathode (100 PPI, 1 cm × 1 cm × 1.2 cm),
constant current = 10 mA, 4 (0.5 mmol), 2 (0.25 mmol),
catalyst (5 mol%), and solvent (6 mL) under atmospheric
air at room temperature for 6 h. Isolated yields.
By contrast, we cannot obtain the
corresponding 4-, 8-, and 10- membered ring
selenomethyl-substituted ethers in Scheme 2, but we
achieved their ring opening products (Scheme 3).
Phthalides, which contain a γ-lactone fused with an
aromatic ring, are ubiquitous structural motifs in
When CH
obtained ring opening products with R =
hydroxyl groups (3k 3n), and the structure of 3k
3
CN was chosen as the solvent, we
[28]
medicinal and natural products. Many approaches
[29]
have been explored to achieve this goal.
The
–
,
primary disadvantages of these methods are long
reaction time, low yield, and use of expensive metal
catalysts. Thus, 2-vinylbenzoic acid (4e) with
different selenides were investigated via the current
electrosynthesis. Furthermore, diphenyl diselenide
with a strong electron-withdrawing group, such as -
CF , can produce the expected product with
3
satisfactory yield. Moreover, diphenyl diselenide with
a fused ring structure can also transform the target
product with 52% yield. Finally, diselenides with
alkyl groups were found to proceed well with 2-
vinylbenzoic acid (4e) to provide the target product
5h at 84% yield. However, the reaction of 2-
vinylbenzoic acid (4e) with diphenyl diselenides
bearing electron-donating groups (OMe) failed to
Scheme 3. Substrate scope of olefinic alcohols. Reaction
conditions: Undivided cell with Pt plate as the anode (1 cm
×
1 cm) and reticulated vitreous carbon (RVC) as the
cathode (100 PPI, 1 cm × 1 cm × 1.2 cm), constant current
=
10 mA, 1 (0.5 mmol), 2a (0.25 mmol), catalyst (5 mol%), produce the desired product 5j. Compared with
and solvent (6 mL) under atmospheric air at room
temperature for 6 h. Isolated yields.
previous literature reports, our strategy for building
b
3
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Advanced Synthesis & Catalysis
10.1002/adsc.201901115
phthalide structures can circumvent the drawbacks
mentioned above.
Some control experiments were performed to gain
additional insights into this selenylation reaction.
Initially, hex-5-en-1-ol (1b) and diphenyl diselenide
(
2a) were reacted with NH I in the absence of current.
4
No reaction was observed between the two raw
materials (Scheme 5, Eq. 1). Subsequently, hex-5-
en-1-ol (1b) and diphenyl diselenide (2a) were
reacted with I without current, and product 3b was
2
obtained with 50% isolated yield (Scheme 5, Eq. 2).
Finally, TEMPO/BHT, 1a, and 2a were reacted under
standard conditions, and the target product 3b was
produced
in
75%/74%
isolated
yields,
correspondingly (Scheme 5, Eq. 3). These results
might exclude the possibility of a radical mechanism.
We also did a controlled experiment in a divided cell,
no product 3b was obtained (Scheme 5, Eq. 4). This
result proved that the regeneration of iodide is from
the reduction of iodine at cathode.
Figure 2. Cyclic voltammograms of reactants and their
mixtures in 0.1 M LiClO /CH CN using a glassy carbon
4 3
disk (3 mm diameter), Pt disk, and Ag/AgCl (in saturated
KCl solution) as working counter, and reference electrodes,
respectively, at a scan rate of 100 mV/s: (a) background,
(
b) 1a (10 mmol/L), (c) 2a (10 mmol/L), (d) NH
mmol/L) , (e) NH I (2 mmol/L)+ 1a (10 mmol/L), (f) NH
2 mmol/L)+ 2a (10 mmol/L)
4
I (2
4
4
I
(
−
the anode, the electrochemical oxidation of I initially
+
results in the formation of I by losing two electrons,
which then react with olefinic alcohols to provide the
iodonium cations intermediate A. The intermediate A
undergoes intramolecular cyclization and releases a
proton to afford intermediate B. Finally, the target
product 3 and a half molar equivalent of I
2
are
At the
and proton are reduced to the iodine
[31]
obtained by a rapid chemical selenation.
cathode, The I
2
anion and hydrogen, which completes the rection
cycle.
Scheme 5. Control experiments.
Lastly, cyclic voltammetry experiments were
performed to enhance the understanding of the
reaction relationship between substrates. As shown in
Figure 2, curve b (substrate 1a) and curve c (substrate
2
a) had no oxidation peak when the potential was less
than 0.8 V. In order to investigate whether the NH
plays a redox role in the reaction, we had measured
the curve of NH I separately (curve d).The CV of
NH I (curve d) displays two oxidation peaks at 0.38
V (Ox ) and 0.67 V (Ox ) versus Ag/AgCl, and these
two anodic peaks of iodide were attributed to I anion
4
I
4
4
1
2
Scheme 6. Plausible mechanism.
-
-
to I
2
and I
3
2
to I , respectively. The curves of NH
4
I
In summary, we have developed a metal- and
oxidant-free electrolysis method for synthesizing
selenomethyl-substituted cyclic ethers and lactones
in the presence of a catalytic amount of ammonium
iodide at room temperature from selenides and
unsaturated alcohols or acids, respectively. Notably,
medium-sized ethers (7-, 9-, and 11-membered ring)
and 4–6-membered ring lactones can be obtained
with 1a (curve e) and NH
also measured, respectively, as shown in Figure 2,
and there was no change, which indicated that I did
not oxidize the substrates in this reaction.
4
I with 2a (curve f) were
-
[30]
On the basis of the above mentioned results, a
plausible mechanism was proposed (Scheme 6). At
4
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Advanced Synthesis & Catalysis
10.1002/adsc.201901115
smoothly via this straightforward route because these
transformations are difficult in conventional
technologies. Moreover, this environment-friendly
strategy is applicable to preparing a wide array of Se-
containing phthalides. Some notable features of this
electrochemical method are broad substrate scope,
convenient operation, inexpensive electrolyte
requirement, high conversion efficiency, and
practicality.
Rowand, S. D. Levine, M. P. Wachter, R. E. Adams,
D. W. Hahn, J. Med. Chem. 1985, 28, 796–803.
[3] M. I. Alam, T. S. Khan, M. A. Haider, ACS
Sustainable Chem. & Eng. 2019, 7, 2894-2898.
4] D. J. Menger, J. J. A. Vanloon, W. Takken, Med. Vet.
Entomol. 2014, 28, 407–413.
5] The forty-ninth meeting of the Joint FAO/WHO
Expert Committee on Food Additives; WHO food
additive series 40; WHO: Geneva, 1998.
6] F. Mehl, I. Bombarda, N. Vanthuyne, R. Faure, E. M.
Gaydou, Food Chem. 2010, 121, 98–104.
7] a) J. S. Clark, Chem. Commun., 2006, 3571–3581; b)
J. Skardon-Duncan, M. Sparenberg, A. Bayle, S.
Alexander, J. S. Clark, Org. Lett. 2018, 20, 2782–
[
[
[
[
Experimental Section
Pent-4-en-1-ol 1a or pent-4-enoic acid 4c (0.5 mmol, 1.0
equiv), diphenyl diselenide (0.25 mmol, 0.5 equiv), and
NH I (0.1 mmol, 5 mol%) were placed in a 10 mL three-
4
necked round-bottomed flask. The flask was equipped with
a condenser, RVC (100 PPI, 1 cm × 1 cm × 1.2 cm)
cathode, and a platinum plate (1 cm × 1 cm) anode.
2
786; c) A.-L. Lee, S. J. Malcolmson, A. Puglisi, R. R.
Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2006,
28, 5153–5157; d) A. E. Sutton, B. A. Seigal, D. F.
Finnegan, M. L. Snapper, J. Am. Chem. Soc. 2002,
24, 13390–13391.
8] a) S. Sathyamoorthi, J. D. Bois, Org. Lett. 2016, 18,
308–6311; b) T. Dohi, N. Takenaga, A. Goto, A.
1
1
[
3
CH CN (6 mL) was added. Electrolysis was performed at
6
room temperature using a constant current of 10 mA until
complete consumption of the substrate (monitored by TLC,
approximately 6 h). Water (30 mL) and ethyl acetate (30
ml) were added. The phases were separated, and the
aqueous phase was extracted with ethyl acetate (2 × 30
mL). The combined organic solution was dried over
Maruyama, Y. Kita, Org. Lett. 2007, 16, 3129–3132;
c) G. Pandey, S. Pal, R. Laha, Angew. Chem. Int. Ed.
2013, 52, 5146–5149; d) H. Nakatsuji, Y. Sawamura,
A. Sakakura, K. Ishihara, Angew. Chem. Int. Ed. 2014,
53, 6974–6977.
4
anhydrous MgSO , filtered, and concentrated under
[
[
9] T. Teduka, H. Togo, Synlett, 2005, 6, 923–926.
10] a) S. T. Manjare, Y. Kim, D. G. Churchill, Acc. Chem.
Res. 2014, 47, 2985–2998; b) G. Mugesh,W.-W. du
Mont, H. Sies, Chem. Rev. 2001, 101, 2125–2179; c)
C. W. Nogueira, G. Zeni, J. B. T. Rocha, Chem. Rev.
reduced pressure. The residue was subjected to
chromatography via silica gel elution with ethyl
acetate/petroleum ether to yield product 2-((phenylselanyl)
-
-
methyl)tetrahydrofuran 3a or 5-((phenylselanyl)methyl)di
hydrofuran-2(3H)-one 5c.
2
004, 104, 6255–6285.
[
[
11] F. Cui, J. Chen, Z. Mo, S. Su, Y. Chen, X. Ma, H.
Tang, H. Wang, Y. Pan, Y. Xu, Org. Lett. 2018, 20,
925–929.
Acknowledgements
12] a) R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev.
2
011, 111, 2981–3019; b) R. Giri, S. KC, J. Org.
We thank the National Natural Science Foundation of China
Chem. 2018, 83, 3013–3022.
(
21861006), Ministry of Education of China (IRT_16R15),
Guangxi Natural Science Foundation of China
2016GXNSFEA380001, 2016GXNSFGA380005,
018GXNSFBA281151), Guangxi Key R&D Program (No.
[
[
13] Z. Liu, H.-Q. Ni, T. Zeng, K. M. Engle, J. Am. Chem.
Soc. 2018, 140, 3223–3227.
14] a) B. Shrestha, P. Basnet, R. K. Dhungana, S. KC, S.
Thapa, J. M. Sears, R. Giri, J. Am. Chem. Soc. 2017,
(
2
AB18221005), Science and Technology Major Project of Guangxi
AA17204058-21), Guangxi science and technology base and
1
39, 10653–10656; b) J.-W. Gu, Q.-Q. Min, L.-C. Yu,
X. Zhang, Angew. Chem. Int. Ed. 2016, 55, 12270–
2274.
(
special talents (guike AD19110027), Guangxi Funds for
Distinguished Experts and State Key Laboratory for Chemistry
and Molecular Engineering of Medicinal Resources
1
[
[
15] a) F. Wang, D. Wang, X. Mu, P. Chen, G. Liu, J. Am.
Chem. Soc. 2014, 136, 10202–10205; b) Y.-T. He, L.-
H. Li, Y.-F. Yang, Z.-Z. Zhou, H.-L. Hua, X.-Y. Liu,
Y.-M. Liang, Org. Lett. 2014, 16, 270–273.
(CMEMR2019-A03) for financial support.
16] a) W. Kong, N. Fuentes, A. García-Domínguez, E.
References
Merino, C. Nevado, Angew. Chem. Int. Ed. 2015, 54,
2
487–2491; b) A. K. Singh, R. Chawla, L. D. S.
[
[
1] a) P. A. Clarke, S. Santos, Eur. J. Org. Chem. 2006,
Yadav, Tetrahedron Lett. 2014, 55, 4742–4746.
17] Y. Wang, L. Zhang, Y. Yang, P. Zhang, Z. Du, C.
Wang, J. Am. Chem. Soc. 2013, 135, 18048–18051.
18] M. J. Harper, E. J. Emmett, J. F. Bower, C. A. Russell,
J. Am. Chem. Soc. 2017, 139, 12386–12389.
19] a) D.-F. Lu, C.-L. Zhu, Z.-X. Jia, H. Xu, J. Am.
Chem. Soc. 2014, 136, 13186-13189; b) P. Wu, K. Wu,
L. Wang, Z. Yu, Org. Lett. 2017, 19, 5450–5453.
2
1
045–2053; b) T. Nakata, Chem. Soc. Rev., 2010, 39,
955–1972; c) Z. Zhang, N. A. Butt, W. Zhang,
[
[
[
Chem. Rev. 2016, 116, 14769–14827; d) K. J. R.
Murauski, A. A. Jaworski, K. A. Scheidt, Chem. Soc.
Rev. 2018, 47, 1773–1782; e) S. Pal, V. Chatare, M.
Pal, Curr. Org. Chem. 2011, 15, 782–800.
2] R. M. Kanojia, E. Chin, C. Smith, R. Chen, D.
5
This article is protected by copyright. All rights reserved.

Advanced Synthesis & Catalysis
10.1002/adsc.201901115
[
20] a) J. Xu, X. Li, Y. Gao, L. Zhang, W. Chen, H. Fang,
Green Chem. 2019, 21, 3807–3811.
G. Tang, Y. Zhao, Chem. Commun. 2015, 51, 11240–
[27] CCDC 1897763 (3i) and CCDC 1897764 (3k)
contain the supplementary crystallographic data for
this paper. The data can be obtained free of charge
from the Cambridge CrystallographicData Centre via
www.ccdc.cam.ac.uk/data_request/cif.
1
1243; b) G.-Y. Zhang, C.-K. Li, D.-P. Li, R.-S. Zeng,
A. Shoberu, J.-P. Zou, Tetrahedron Lett. 2016, 72,
972–2978; c) S.-S. Zhang, J. Xia, J.-Q. Wu, X.-G.
Liu, C.-J. Zhou, E. Lin, Q. Li, S.-L. Huang, H. Wang,
2
Org. Lett. 2017, 19, 5868–5871; d) S. Tang, D. Wang, [28] a) X. Pang, X. Lin, J. Yang, X. Zhou, B. Yang, J.
Y. Liu, L. Zeng, A. Lei, Nat. Commun. 2018, 9, 798–
Wang, Y. Liu, J. Nat. Prod. 2018, 81, 1860-1868; b)
W. Fang, J. Wang, J. Wang, L. Shi, K. Li, X. Lin,Y.
Min, B. Yang, L. Tang, Y. Liu, X. Zhou, J. Nat.
Prod. 2018, 81, 1405-1410; c) H. Kamauchi, Y.
Shiraishi, A. Kojima, N. Kawazoe, K. Kinoshita, K.
Koyama, J. Nat. Prod. 2018, 81, 1290-1294; d) D. R.
McMullin, B. D. Green, N. C. Prince, J. B. Tanney, J.
D. Miller, J. Nat. Prod. 2017, 80, 1475-1483; e) L.
Zuo, Z. Sun, Y. Hu, Y. Sun, W. Xue, L. Zhou, J.
Zhang, X. Bao, Z. Zhu, G. Suo, X. Zhang, J
Pharmaceut. Biomed. Anal. 2017, 137 220–228.
8
05.
[
21] a) Q. Lu, J. Zhang, F. Wei, Y. Qi, H. Wang, Z. Liu, A.
Lei, Angew. Chem. Int. Ed. 2013, 52, 7156–7159; b)
Q. Xue, J. Xie, P. Xu, K. Hu, Y. Cheng, C. Zhu, ACS
Catal., 2013, 3, 1365–1368; c) C. Liu, M. Zhu, W.
Wei, D. Yang, H. Cui, X. Liu, H. Wang, Org. Chem.
Front. 2015, 2, 1356–1360.
[
[
22] a) L. Zheng, H. Huang, C. Yang, W. Xia, Org. Lett.
2
015, 17, 1034−1037; b) D. Zhang, H. Wang, C.
Bolm, Chem. Commun. 2018, 54, 5772–5775.
[
29] a) R. Karmakar, P. Pahari, D. Mal, Chem. Rev. 2014,
23] a) Y. Jiang, K. Xu, C. Zeng, Chem. Rev. 2018, 118,
114, 6213-6284; b) S. Borthakur, S. Baruah, B. Sarma,
4
485−4540; b) M. Yan, Y. Kawamata, P. S. Baran,
Chem. Rev. 2017, 117, 13230−13319.
24] C.-Y. Cai, H.-C. Xu, Nat. Commun. 2018, 9, 3551–
S. Gogoi, Org. Lett., 2019, 21, 2768-2771; c) S. K.
Ray, M. M. Sadhu, R. G. Biswas, R. A. Unhale, V. K.
Singh, Org. Lett. 2019, 21, 417-422.
[
[
3
558.
25] a) F. V. Singh, T. Wirth, Org. Lett. 2011, 13, 6504–
[30] a) L.-S. Kang, M.-H. Luo, C. M. Lam, L.-M. Hu, R.
D. Little, C.-C. Zeng, Green Chem. 2016, 18, 3767–
3774. b) Q.-Q. Wang, K. Xu, Y.-Y. Jiang, Y.-G. Liu,
B.-G. Sun, C.-C. Zeng, Org. Lett. 2017, 19, 5517-
5520.
6
1
507. b) G. Pandey, B. B. V. S. Sekhar, J. Org. Chem.
992, 57, 4019-4023. c) A. A. Vieira, J. B. Azeredo,
M. Godoi, C. Santi, E. N. S. Júnior, A. L. Braga, J.
Org. Chem. 2015, 80, 2120−2127.
[
26] a) Z.-Y. Mo, T. R. Swaroop, W. Tong, Y.-Z. Zhang,
H.-T. Tang, Y.-M. Pan, H.-B. Sun, Z.-F. Chen, Green
Chem. 2018, 20, 4428–4432; b) Y.-Z. Zhang, Z.-Y.
Mo, H.-S. Wang, X.-A. Wen, H.-T. Tang, Y.-M. Pan,
[31] X. Zhang, C. Wang, H. Jiang, L. Sun, Chem. Commun.
2018, 54, 8781-8784.
6
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Advanced Synthesis & Catalysis
10.1002/adsc.201901115
COMMUNICATION
Electrochemical Difunctionalization of Olefines:
Access to Selenomethyl-Substituted Cyclic Ethers
or Lactones
Adv. Synth. Catal. Year, Volume, Page – Page
a,c
a,c
Xiu-Jin Meng,
Ping-Fu Zhong, Yu-Mei
a
,a
,a
Wang, Heng-Shan Wang,* Hai-Tao Tang,*
and Ying-Ming Pan*,
a,b
7
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