Visible light-promoted, iodine-catalyzed selenoalkoxylation of olefins with diselenides and alcohols in the presence of hydrogen peroxide/air oxidant: an efficient access to α-alkoxyl selenides

Article abstract of DOI:10.1007/s11426-017-9158-y

Under iodine-catalyzed and visible light-irradiated aerobic conditions, selenoalkoxylation of olefins with diselenides and alcohols can be efficiently achieved to afford the useful α-alkoxyl selenides in the presence of only 0.5 equiv. of H₂O₂. Controlling the sub-stoichiometric H₂O₂ amount is crucial to avoid the non-selective over-oxidation of the diselenides that leads to the ineffective hyper-valent selenium compounds. Meanwhile, under visible light irradiation, the green, safe, and low-cost air can work as a supplemental mild oxidant in the reaction to ensure selective oxidation of the diselenides, full conversion of the reactants, and ultimately good yield of the products.

Full text of DOI:10.1007/s11426-017-9158-y

SCIENCE CHINA
Chemistry
https://doi.org/10.1007/s11426-017-9158-y
• ARTICLES •
Visible light-promoted, iodine-catalyzed selenoalkoxylation of
olefins with diselenides and alcohols in the presence of hydrogen
peroxide/air oxidant: an efficient access to α-alkoxyl selenides
Mingxuan Liu1,2, Yiming Li2, Lei Yu1*, Qing Xu1 & Xuefeng Jiang2*
1Institute of Pesticide, School of Chemistry and Chemical Engineering and School of Horticulture and Plant Protection, Yangzhou University,
Yangzhou 225002, China
2Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, Shanghai
200062, China
Received September 13, 2017; accepted October 16, 2017; published online December 27, 2017
Under iodine-catalyzed and visible light-irradiated aerobic conditions, selenoalkoxylation of olefins with diselenides and alcohols
can be efficiently achieved to afford the useful α-alkoxyl selenides in the presence of only 0.5 equiv. of H2O2. Controlling the
sub-stoichiometric H2O2 amount is crucial to avoid the non-selective over-oxidation of the diselenides that leads to the ineffective
hyper-valent selenium compounds. Meanwhile, under visible light irradiation, the green, safe, and low-cost air can work as a
supplemental mild oxidant in the reaction to ensure selective oxidation of the diselenides, full conversion of the reactants, and
ultimately good yield of the products.
selenium, alkoxyl selenide, aerobic oxidation, visible light, iodine catalysis
Citation:
Liu M, Li Y, Yu L, Xu Q, Jiang X. Visible light-promoted, iodine-catalyzed selenoalkoxylation of olefins with diselenides and alcohols in the presence
of hydrogen peroxide/air oxidant: an efficient access to α-alkoxyl selenides. Sci China Chem, 2017, 60, https://doi.org/10.1007/s11426-017-9158-y
1 Introduction
also very interested in screenings of organoselenium com-
pounds that might serve as the starting materials for selenium
catalyst development. Recently, α-alkoxylselenides came
into our sight because of their unique chemical structures.
The selenium-containing moieties of these compounds might
have catalytic activities, while the adjacent alkoxyl group
might allow fixing these molecules onto solid phase carriers
to develop the recyclable heterogeneous catalysts [5b,7]. In
addition, the adjacent oxygen and selenium groups might
well coordinate with transition metals to prepare novel metal
complexes with potential unique catalytic activity [8].
Currently, α-alkoxyl selenides can be directly synthesized
through the selenoalkoxylation reaction of alkenes with elec-
trophilic organoselenium compounds (e.g., RSeBr, RSeCl,
etc.) and alcohols, which employs the sensitive organose-
lenium halides, resulting in the undesirable side reactions
Organoselenium compounds have been widely used in
biochemistry, medicinal chemistry, organic synthesis, and
material science [1,2]. Recently, the eco-friendly aspects of
organoselenium chemistry began to draw much attention [3].
Among reported works, organoselenium catalysis [3–5] is an
important subject with good industrial application potential
because of the clean procedures, transition-metal-free condi-
tions and the metabolizable catalytic element, which is safe
to the environment [6]. During the last three years, our group
[5] has been taking great effort in organoselenium-catalyzed
reactions to develop the green synthetic methods. We were
*Corresponding authors (email: yulei@yzu.edu.cn; xfjiang@chem.ecnu.edu.cn)
© Science China Press and Springer-Verlag Berlin Heidelberg 2017
chem.scichina.com link.springer.com

2
Liu et al. Sci China Chem
that leads to the carcinogenic organohalide by-products [9].
The reaction of diselenides with chemical oxidants can gen-
erate the electrophilic organoselenium cations in situ as well,
which avoids the formation of organohalides, but produces
mass wastes in the procedures and limits the further large-
scale applications [10]. Braga et. al. [11] have reported a
nice method to prepare α-alkoxyl selenides through a solvent-
free selenoalkoxylation reaction of alkenes with diselenides
and alcohols, but the reaction employed dimethyl sulphox-
ide (DMSO) as the oxidant that inevitably led to the smelly
by-product Me2S. Moreover, this protocol used micro-wave
as the driven force, which was highly effective in laboratory
but required specialized equipment and might result in the
high energy consumption in large-scale preparation. There-
fore, novel methods that are free of waste generations and
employ renewable energy are still required from the practical
viewpoint.
Yet, reactions driven by visible light have attracted
chemists because of their clean procedures, mild conditions
and simple equipments for industrial production [12,13].
These methods afforded additional opportunities to utilize
sunlight as the abundant, renewable, and clean energy as
well. Recently, we developed an efficient protocol to pre-
pare α-alkoxyl selenides through the visible light-promoted
selenoalkoxylation reaction of alkenes with alcohols and
diselenides. The reactions were catalyzed by low-loading I2
and employed H2O2/air as the clean oxidant that generated
no wastes. Moreover, compared with the reported visible
light-promoted reactions [12,13], the method is free of
the expensive metal complex catalysts or photosensitizers.
Herein, we wish to report our findings.
initially added into a reaction tube. Air was then introduced
at the rate of 0.88ꢀcm3/s into the system and at room tempera-
ture under the irradiation of a 200ꢀW incandescent light. The
reaction was monitored by thin-layer chromatography (TLC).
When the reaction terminated, the solvent was evaporated un-
der reduced pressure. The residue was purified by column
chromatography (EtOAc/petroleum ether: 1/20) to give the
corresponding compounds 4. For the reaction with PhCH2OH
(Table 2, vide infra, entry 8 in text), 1ꢀmmol of PhCH2OH was
employed and the reaction was performed in 1ꢀmL of MeCN
solvent. The characterization data and NMR spectra of the
compounds were given in Supporting Information online.
2.3 Detailed procedure for the outdoor reaction under
sunlight
1ꢀmmol of styrene 1a, 0.5ꢀmmol of diphenyl diselenide
2a, 1ꢀmL of ethanol 3a, 0.5ꢀmmol of 30 w/w% H2O2 and
0.1ꢀmmol of iodine were initially added into a reaction
tube. Air was then introduced into the system at the rate
of 0.88ꢀcm3/s and at room temperature under sunlight for
20ꢀh, totally. The reaction was performed in sunny days in
the summer of 2016. It spent two days and the reaction time
was from 7ꢀa.m. to 5 p.m. for each day. When the reaction
terminated, the solvent was evaporated under reduced pres-
sure. The residue was purified by column chromatography
(EtOAc/petroleum ether: 1/20) to give the corresponding
compound 4a in 95% yield.
3 Results and discussion
The selenoalkoxylation reaction of styrene 1a with (PhSe)2
and EtOH was initially employed to optimize the reaction
conditions. Irradiating the solution of styrene 1a (1 M) and
(PhSe)2 2a (0.5 M) in EtOH 3a with sub-stoichiometric H2O2
oxidant (50ꢀmol%) by a 200ꢀW incandescent lamp for 20ꢀh af-
forded the desired adduct 4a in 45% yield (Table 1, entry 1).
Further screenings demonstrated that addition of catalytic I2
obviously improved the reaction (Table 1, entries 2–5) and
the product 4a could be obtained in almost quantitative yield
by using 10ꢀmol% of I2, (Table 1, entry 5). Experiment per-
formed under N2 protection decreased the product yield, in-
dicating that air might participate as an additional oxidant in
the process (Table 1, entry 6). Nevertheless, the reactions
were retarded without H2O2 even when performed in pure
O2 atmosphere (Table 1, entries 7, 8); Extending the reaction
time only slightly enhanced the product yield in the absence
of H2O2 (Table 1, entry 9). The effect of H2O2 amount was
also examined and using 50ꢀmol% of H2O2 was found to be
the preferable condition (Table 1, entries 5 vs. 10–12). In-
creased H2O2 amount contrarily reduced the product yield,
probably due to the over-oxidation of (PhSe)2 into PhSeO3H,
which was ineffective for the reaction (Table 1, entries 11–12)
[5].
2 Experimental
2.1 General methods
All solvents employed were analytical pure (AR) and were di-
rectly used. Reagents were purchased from the reagent mer-
chant and their purities were more than 98% and were di-
rectly used. Styrene is distilled by vacuum distillation be-
fore using. IR spectra were measured on Bruker Tensor 27
Infrared spectrometer (Germany). H and 13C NMR spectra
1
were recorded on a Bruker Avance 600/400 instrument (600
or 400ꢀMHz for 1H NMR and 150 or 100ꢀMHz for 13C NMR)
using CDCl3 as the solvent and Me4Si as the internal stan-
dard. Chemical shifts for 1H and 13C NMR were reported in
parts per million (ppm). Mass spectra were measured on a
Shimadzu GCMS-QP2010 Ultra spectrometer (EI) and maxis
(ESI) (Japan).
2.2 General procedure for the preparation of 4
1 mmol of olefin 1, 0.5ꢀmmol of selenide 2, 1ꢀmL of alcohol
3, 0.5ꢀmmol of 30 w/w% H2O2 and 0.1ꢀmmol of iodine were

Liu et al. Sci China Chem
3
Table 1 Condition optimizationsa)
Entry
1
I2 (mol%)
H2O2 (mol%)
Atm.
air
air
air
air
air
N2
air
O2
O2
air
air
air
4a (%)b)
45
–
50
50
50
50
50
50
–
2
2
75
3
6
82
4
8
90
5
10
10
10
10
10
10
10
10
99
6
50
7
60
–
8
65
69c)
–
9
10
11
12
40
80
160
91
88
53
a) 1ꢀmmol of 1a and 0.5ꢀmmol of 2a in 1ꢀmL of EtOH were irradiated by a 200ꢀW incandescent lamp at room temperature for 20ꢀh; b) isolated yields based
on 1a; c) the reaction time was extended to 60ꢀh.
Table 2 Synthesis of α-alkoxyl selenidesa)
Entry
1
R1, R2
Ph, H
R
R′
Et
4: yield (%)b)
4a: 99, 97c)
4b: 69 (79)
4c: 98
Ph
2
Ph, H
3-FC6H4
Et
3
Ph, H
4-FC6H4
Et
4
Ph, H
4-MeC6H4
Et
4d: 76
5
Ph, H
4-MeOC6H4
Et
4e: 86
6
Ph, H
n-Bu
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Et
4f: 41 (50)
4g: 98
4h: 90d)
7
Ph, H
Me
PhCH2
c-C6H11
i-Pr
t-Bu
Et
8
Ph, H
9
Ph, H
4i: 61
10
11
12
13
14
15
16
17
Ph, H
4j: 47 (70)
4k: 41 (51)
4l: 86
Ph, H
4-BrC6H4, H
4-ClC6H4, H
4-MeC6H4, H
4-ClC6H4, Me
Ph, c-C6H11
Ph, Ph
Et
4m: 90
Et
4n: 99
Et
4o: 73
Et
4p: 80
4q: 40 (51)e)
Et
4-ClC6H4,
4-ClC6H4
18
Ph
Et
Et
4r: 40 (53)
4s: 70
19
Ph
a) Without special instructions, the reactions were performed under optimized conditions described in Table 1, entry 5; b) isolated yields based on the feed
amount of 1 outside the parentheses; isolated yields based on the converted 1 inside the parentheses; c) reaction performed at 10 mmol-scale; d) 1ꢀmmol of
benzyl alcohol and 1ꢀmL of MeCN were employed; e) reaction time was extended to 48ꢀh.

4
Liu et al. Sci China Chem
Under the optimized conditions, a series of α-alkoxyl se-
lenides 4 were then synthesized (Table 2). It was found that
both of the electron-deficient or -enriched diaryl diselenides
led to the corresponding α-alkoxyl selenides 4a–4e smoothly
in 69%–99% yields (Table 2, entries 1–5). Dialkyl dise-
lenide (n-BuSe)2 as substrate was also tested, but the reac-
tion proceeded slowly and gave the desired product 4f in
low yield, while the starting materials were not converted
completely (Table 2, entry 6). Primary alcohols, such as
EtOH, MeOH, and PhCH2OH, were preferable for the reac-
tion, affording the corresponding product 4a, 4g, and 4h in
excellent yields (Table 2, entries 1, 7, 8), while secondary or
tertiary alcohols were obviously unfavorable substrates and
gave the related products in decreased yields (Table 2, en-
tries 9–11). It was found that both electron-enriched and-de-
ficient styrene derivatives led to the corresponding α-alkoxyl
selenides smoothly in good to excellent yields (Table 2, en-
tries 12-14). 1-Alkyl-1-aryl-substituted ethenes afforded the
products in good yields (Table 2, entries 15, 16), but the
1,1-bisaryl-substituted alkenes were obviously not preferable
for the reaction, giving 4q and 4r in poor yields even with
extended reaction time (Table 2, entries 17, 18). Exocyclic
alkene 1s was also fit for the reaction, affording 4s in 70%
yield (Table 2, entry 19). The reaction of the cyclic alkenes
cyclohexene (1t) and 1-phenylcyclohexene (1u) with dise-
lenide and alcohol led to the α-alkoxyl selenides 4t and 4u,
which were syn-adducts, as confirmed by the nuclear over-
hauser effect spectroscopy (NOESY) analysis (Figure 1, for
details please see Supporting Information online). The re-
action of 1,2-disubstited alkene, such as 1,2-diphenylethene,
was tested, but was retarded under the mild visible light-ir-
radiation conditions. Benzoic acid, the oxidative C=C cleav-
age by-product was generated and detected in gas chromatog-
raphy-mass spectrum (GC-MS) after heating at 80 °C in a
sealed tube.
Figure 1 NOESY study of the products 4t and 4u (color online).
Reactions of 1a with 2a in EtOH driven by different light
sources were also examined. As shown in Eq. (1), the reac-
tions irradiated by LEDs blue or white light both led to very
good product yields at 90% and 91%, respectively. An out-
door experiment under sunlight afforded the product 4a in
95% yield. The results clearly showed the possibility for the
utilization of solar energy in this reaction for future indus-
trial-scale production.
Mechanisms of this interesting reaction were our next con-
cern and a series of control experiments were conducted. The
reaction was slowed down without light irradiation (Table 3,
entry 1) and was further restrained in dark (Table 3, entries 2,
3). Comparison of the results with those in Table 1, entries 5,
6 indicated that the use of air as oxidant required visible light
irradiation as the driven force. Without I2, the product was
obtained in very low yield (Table 3, entries 4, 5). No reac-
tion occurred when H2O2 was further removed (Table 3, entry
6). But with sufficient I2 (50–100ꢀmol%), the reaction could
occur even without H2O2 in dark and under N2 protection to
give 4a in 48%–89% yields and AgI precipitations could be
observed after adding the solutions into aqueous AgNO3
Table 3 Control experimentsa)
c)
Entry
Conditionsb)
Without additional light irradiation (ambient light), I2 (10%), H2O2 (50%), air
In dark, I2 (10%), H2O2 (50%), air
C1a
73
4a (%)d)
70
1
2
63
58
3
In dark, I2 (10%), H2O2 (50%), N2
47
43
4
In dark, H2O2 (50%), air
14
12
5
In dark, H2O2 (50%), N2
11
10
6
In dark, N2
0
0
7
In dark, I2 (50%), N2
61
48
8
In dark, I2 (100%), N2
>99e)
>99e)
>99e)
>99e)
89
9
Visible light irradiation, I2 (10%), H2O2 (50%), air hydroquinone (100%)
Visible light irradiation, I2 (10%), H2O2 (50%), air TEMPO (100%)
Visible light irradiation, I2 (10%), H2O2 (50%), air AIBN (100%)
91
10
11
93
45f)
a) 1ꢀmmol of 1a, 0.5ꢀmmol of 2a, and 1ꢀmL of EtOH were employed; the reactions were conducted at room temperature for 20ꢀh; b) molar ratio of I2, H2O2
or additives based on 1a inside the parentheses; c) conversion ratio of 1a determined by GC; d) isolated yields of 4a based on 1a; e) full conversion of 1a; f)
reaction finished within 4ꢀh

Liu et al. Sci China Chem
5
(Table 3, entries 7, 8), showing that the re-oxidation of the
generated HI into I2 by H2O2 or air should be a crucial step
in the I2 catalysis circle. Although (PhSe)2 might generate
free radicals under the visible light irradiation conditions [1e],
the addition of hydroquinone or 2,2,6,6-tetramethylpiperidi-
nooxy (TEMPO) as free radical scavenger did not obviously
restrain the reaction (Table 3, entries 9, 10), while the addition
of free radical initiator azodiisobutyronitrile (AIBN) resulted
in the decreased 4a yield and the generation of many uniden-
tified by-products on the contrary (Table 3, entry 11), indicat-
ing that free-radical mechanisms should be excluded during
the processes. In summary, the above experimental results
showed that the alkene selenoalkoxylation occurred through
an I2-initiated non-free radical reaction which might release
HI. In the process, H2O2 and air were crucial oxidants to re-
generate I2 from HI and the aerobic oxidation of HI required
visible light irradiation condition.
backside led to the intermediate 6, in which the bulky sele-
nium groups were at the less steric hindrance carbon. An-
other nucleophilic substitution of alcohol with 6 afforded the
product 4 and HI (Table 3, entries 7, 8), which could be re-ox-
idized into I2 by H2O2 or air and the oxidation of HI by air
was driven by visible light irradiation. As indicated by the
results in Table 3, entries 9–11, the reactions of diselenides
in the presence of strong oxidants were inclined to occur via
electrophilic processes [16], which contributed to the high
stereo-selectivity for cyclic alkene substrates and led to only
syn-adducts (Figure 1) because of the double SN2 attacks
from the backsides (Scheme 1), as reported by Denmark’s
group in 2015 [4c].
4 Conclusions
In conclusion, an efficient alkene selenoalkoxylation method
for the synthesis of α-alkoxyl selenides was developed. In the
reaction, controlling of the sub-stoichiometric H2O2 amount
was crucial to avoid the non-selective over-oxidation of dis-
elenides. Catalyzed by I2 and under visible light irradiation,
air could be utilized as a supplemental oxidant to achieve the
full conversion of alkenes and diselenides. Further investiga-
tions on the applications of α-alkoxyl selenides in selenium
catalyst development are on the way in our laboratory.
On the basis of the above experimental results as well as
Refs. [14–16], a possible mechanism was supposed. First
of all, as supported by the result of our previous 77Se NMR
studies [5a], the oxidation of (PhSe)2 with 1 equiv. of H2O2
could furnish PhSeOH (Eq. (2)).
Acknowledgments This work was supported by the National Natural
Science Foundation of China (21202141, 21672069), Priority Academic
Program Development of Jiangsu Higher Education Institutions, the Open
Project Program of Jiangsu Key Laboratory of Zoonosis (R1509) and the
High Level Talent Support Project of Yangzhou University. We thank the
testing centre of Yangzhou University for assistances.
In the reaction, the amount of H2O2 was controlled to
be sub-stoichiometric to avoid the possible non-selective
over-oxidation that might lead to the hyper-valent selenium
species, which were ineffective for the reaction (Table 1,
entries 5 vs. 11, 12) [5]. The reaction of styrene with Ph-
SeOH and ethanol could afford the desired product 4a, but
because of the sub-stoichiometric H2O2 amount, styrene and
diselenide could not be completely converted (Table 1, entry
1). Addition of I2 led to PhSeI [14], which was more active
than PhSeOH and soon reacted with alkenes [15] to generate
the onium 5 (Scheme 1). Nucleophilic attack of I− at the
Conflict of interest
The authors declare that they have no conflict of
interest.
Supporting information The supporting information is available online
at http://chem.scichina.com and http://link.springer.com/journal/11426.
The supporting materials are published as submitted, without typesetting
or editing. The responsibility for scientific accuracy and content remains
entirely with the authors.
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