Oxone-Mediated Oxidation of Vinyl Selenides in Water

Article abstract of DOI:10.1002/ejoc.201800498

A simple and practical procedure for the oxidation of vinyl selenides into the corresponding selenones using Oxone in water at 60 °C has been reported. Structurally diverse phenyl vinyl selenones were oxidized under heterogeneous conditions without organi

Full text of DOI:10.1002/ejoc.201800498

A Journal of
Accepted Article
Title: Oxone mediated oxidation of vinyl selenides in water
Authors: Martina Palomba, Francesco Trappetti, Luana Bagnoli,
Claudio Santi, and Francesca Marini
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10.1002/ejoc.201800498
European Journal of Organic Chemistry
FULL PAPER
Oxone mediated oxidation of vinyl selenides in water
Martina Palomba,[a] Francesco Trappetti,[a] Luana Bagnoli,[a] Claudio Santi[a] and Francesca Marini*[a]
Abstract: A simple and practical procedure for the oxidation of vinyl
selenides into the corresponding selenones using Oxone in water at
60 °C has been reported. Structurally diverse phenyl vinyl selenones
were oxidized under heterogeneous conditions without organic co-
solvents or additional catalysts.
for the domino synthesis of carbo- and hetero-cycles,[11] and for
the synthetically challenging, enantioselective construction of
quaternary stereocenters via organocatalysis.[12] They found also
useful applications in natural product synthesis[12g] and in
nucleoside[13] and carbohydrate[14] chemistry. Many of the
developed transformations are Michael-initiated domino
reactions in which the selenonyl moiety consecutively plays
different roles as strong electron-withdrawing group in the
Introduction
Michael step, as efficient leaving group in the next nucleophilic
[11f]
substitution and, in one case
also as an oxidant after the
Selenones are organic compounds containing a hexavalent,
tetra-coordinated selenium species.[1] These compounds are
accessible by direct oxidation of selenides. The initially formed
tetravalent selenoxides are converted into the selenones by
using an excess of oxidant. Despite the formal similarities, redox
properties of selenides are quite different in respect to the
analogous sulfides.[1,2] The Se=O bonds have more dipolar
character than S=O bonds and, even though the first oxidation of
selenides to selenoxides is fast, the decreased electron density
on the selenium atom makes selenoxides less susceptible to
further oxygen transfer. As a consequence, only few oxidizing
agents are strong enough to convert selenides into the
corresponding selenones. Organic peroxyacids,[3] such as m-
chloroperbenzoic acid (m-CPBA) or trifluoroperacetic acid in
MeOH or dichloromethane, and magnesium bis(monoperoxy
phtalate) (MMPP)[4] in alcohols or THF have been successfully
employed. Hydrogen peroxide with catalytic amounts of
benzenseleninic acid[5] and inorganic oxidants such as
displacement. Despite the increasing attention, few methods are
available for their preparation. In fact, to date, the only effective
access to vinyl selenones relies on the oxidation of the
corresponding selenides[15] with organic peroxyacids, being the
m-CPBA the oxidant of choice.[1d-e,11-14] In light of these facts and
as part of our interest in the chemistry of vinyl selenones, we
decided to explore alternative and greener methods for their
preparation. We were inspired by the wide number of oxidative
protocols recently employed in the synthesis of sulfones, that
involve hydrogen peroxide in the presence of catalysts[16] or
Oxone,[17] (triple salt: 2KHSO5 KHSO4 K2SO4). These oxidants,
due to the non-toxic nature of the by-products, the easy handling
and the low cost are greatly employed for eco-friendly
transformations.[18] Preliminary experiments showed that Oxone
in water without any organic co-solvent, additional catalyst or
promoter generate vinyl selenones in good yields. Structurally
diverse phenyl vinyl selenones have been prepared and
characterized by nuclear magnetic resonance of 77Se. Although
this spectroscopy is considered a very powerful tool for the
characterization of selenium–containing compounds,[19] to date,
only sporadic data are available for selenones.[3,10d-f,12c]
.
.
[3]
potassium permanganate or Oxone[6] are also suitable for the
oxidation. Two procedures employing the HOF.CH3CN complex
prepared by bubbling dilute F2 into aqueous acetonitrile[7] and the
HMPA molibdenum complex [MoO(O)2(H2O)(HMPA)][8] have
been developed recently. All these methods show drawbacks in
terms of safety, cost, waste, or use of heavy metals or
halogenated solvents. Furthermore, none of these protocols is
general, being the efficiency of the methods strictly dependent
from the structural features of the starting selenide. For example,
some selenones are not accessible due to the high instability of
the selenoxide intermediates that spontaneously decompose by
elimination.[9] Moreover, selenones are sensitive to nucleophiles
or bases, due to the excellent leaving ability of the selenonyl
group in nucleophilic substitutions. For this reason in many
cases they undergo further transformations as soon as they are
formed.[6,10] Recently, under-investigated phenyl vinyl selenones
(Scheme 1) have been rediscovered as versatile building blocks
Scheme 1.Synthesis of phenyl vinyl selenones and synthetic applications.
Results and Discussion
[a]
Department of Pharmaceutical Sciences, Group of Catalysis and
Organic Green Chemistry
Table 1 shows the results of the experiments carried out with
different oxidizing systems on the phenyl (E)-2-phenylvinyl
selenide 1a as the model substrate. The results of the typical
reaction with m-CPBA is reported for comparison.
University of Perugia
Via del Liceo, 1 06123 Perugia, Italy
E-mail: francesca.marini@unipg.it
Supporting information for this article is given via a link at the end of
the document.
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10.1002/ejoc.201800498
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All the experiments carried out with H2O2 in combination with
different inorganic catalysts failed to generate the selenones
even after keeping the reactions for 24 hours. In fact, only the
formation of the selenoxide 2a was observed with variable
conversions. The experiment with Oxone in MeOH under
reaction conditions previously reported in the literature[6] for the
oxidation of aryl alkyl selenides (Table 1, entry 5) was also
unsuccessful. In fact, only the 2-methoxy-2-phenylethyl phenyl
selenone 4a was isolated from the crude reaction mixture in
50% yield. The formation of this product can be easily explained:
Oxone converted the vinyl selenide 1a into the corresponding
selenone 3a, but this compound was sensitive to the basic
conditions (pH 11) employed and underwent an intermolecular
oxa-Michael reaction in the presence of methanol. The
experiment carried out in the absence of the basic buffer
afforded the vinyl selenoxide 2a as the major product (Table 1,
entry 6). A greater amount of selenone was obtained when the
reactions were carried out in water without any co-solvent. The
almost exclusive formation of 3a (83% isolated yield) was
observed with 2.2 molar equivalents of Oxone under “on-water”
conditions after 14 h heating at 60 °C (Table 1, entry 12) and
vigorous stirring. Interestingly, the reaction proceeded chemo-
selectively without any epoxidation of the C=C double
bonds[18b,c,f,20] Moreover the method is mild enough to avoid the
addition of water on the electrophilic carbon-carbon double bond.
A control over the degree of oxidation was also possible varying
the oxidant loading and lowering the temperature. In fact, the
selective access to the vinyl selenoxide 2a was performed
working with 0.6 equivalents of Oxone in water at room
temperature (Table 1, entry 11).
The formation of the selenone 3a was also observed in several
protic and aprotic polar organic solvents, but 1H NMR of the
crude reaction mixtures showed consistent amounts of the
selenoxide. Only the oxidation in acetonitrile gave a selenoxide:
selenone ratio comparable with those obtained in water,
however the rate of the oxidation was slower. In fact, an
incomplete conversion of the vinyl selenide 1a was observed,
after identical reaction times (Table 1, entry 14).
In order to explain the role of water, a reaction mechanism has
been proposed. Water not only readily dissolves the Oxone, but
it also modulates the activity of this oxidant.[17a] In fact, the
formation of inter- and intra-molecular hydrogen bonds can
facilitate the oxygen transfer (Scheme 2).
Table 1. Comparative study with various oxidative systems and optimization of
reaction conditions
entry
oxidant
(equiv.)
conditions
t
conv.
(%)[a,b]
2a:3a
[a]
(h)
H2O2 (3)
neat, 75 °C
5
88
90:10
100:0
1
2[16a]
H2O2 (8)
MeCN/0.2 M
NaHCO3, rt
24
100
MnSO4 (0.02)
3[16b]
4[16d]
H2O2 (3)
MeOH/0.1 M
NaOH, rt
7
2
low
low
100:0
100:0
Na2B4O7 (0.1)
H2O2 (8)
neat, rt
H3BO3 (0.5)
5[6]
6
Oxone (2.2)
Oxone (2.2)
Oxone (2.2)
Oxone (2.2)
Oxone (2.2)
Oxone (1.5)
Oxone (0.6)
Oxone (2.2)
Oxone (2.2)
Oxone (2.2)
Oxone (2.2)
MeOH/NaOH, rt
MeOH/H2O, rt
H2O, rt
1
8
100
100
-
72:28
60:40
10:90
30:70
13:87
100:0
5:95
7
8
100
8
H2O, 60 °C
H2O, 60 °C
H2O, 60 °C
H2O, rt
8
100 (80)
100 (77)
100 (70)
100 (72)
100 (83)
100
9
4
10
11
12
13
14
15
16[1f]
24
4
H2O, 60 °C
EtOH, 60 °C
MeCN, 60 °C
DMF, 60 °C
MeOH, rt
14
8
29:71
8:92
8
92
8
100
81:18
7:93
m-CPBA(2.6)
12
100
K2HPO4(4.4)
[a] Conversions and 2a:3a ratios are calculated by 1H NMR on crude mixtures.
[b] Isolated yields are reported in parentheses.
With the best conditions in hand, oxidation reactions of variously
substituted vinyl selenides to selenones were examined.
Compounds 1a-q were treated with 2.2 equivalents of Oxone
.
.
(2KHSO5 KHSO4 K2SO4) in H2O at 60° C without additional
catalysts, co-solvents or buffers. Reaction products, times and
isolated yields are shown in table 2. In parentheses the yields of
oxidation reactions carried out with an excess of m-CPBA (2.6 to
4 equivalents) are reported for comparison. Several - aryl or
alkyl substituted phenyl vinyl selenides were oxidized into the
corresponding selenones in comparable or even better yields
than those obtained with m-CPBA. Work-up and purification
procedures were facilitated in respect to reactions with m-CPBA.
Scheme 2. Plausible mechanism for Oxone mediated oxidations of vinyl
selenides in aqueous medium
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Table 2.Synthesis of the selenones 3[a]
3a,14h, 83%,(90%)[ref11q]
3b, 15h, 68%, (60%)[ref11a]
3c, 3h, 64%, 77%,[b]
3d, 8h, 53%, (63%)[ref11a]
(67%)[11a]
3e, 8h, 86%, (40%)
3f, -(50)[b]
3g, 14h, 89%, (78%)
3h, 15h, 67%, (76%)[ref11o]
3l,[d] 4h, 70%, 84%,[b]
3i, 14h, 45%
3j,[c] 5h, 64%, (45%)[ref11f]
3k,-
(60%)[ref11b]
3m, 4h, 83%,
3n,[d] 8h, 50%, (60%)
3o, 20h, 60%, (44%)
3p, -
3q, 3h, 80%
[a] Yields of the oxidations carried out with m-CPBA are reported in parenthesis for a comparison. [b] Yield calculated on the crude mixture. [c] The reaction was
carried out on a 1:1 mixture of E:Z selenides (by 1H NMR). [d] Reactions with 0.6 equiv.of Oxone gave selenoxides in poor yields.
The reported yields refer to compounds purified by filtration
through a short pad of silica gel, however crude products
obtained by simple extraction of the reaction mixtures with
EtOAc or by filtration of the suspended solid, as for 3c, were
almost pure by 1H NMR analysis. The oxidations of sterically
hindered Z vinyl selenides, such as 3i and 3j were also
successful, albeit in moderate yields. Unfortunately, the butyl
(E)-2-phenylvinyl selenone 3f and the trisubstituted vinyl
selenone 3k could not be formed. Probably, the oxidation of 1f
failed in consideration of the high instability of the alkyl
selenones. In fact, also the crude 3f initially obtained when the
reaction was performed with m-CPBA in dichloromethane, gave
rapid decomposition during the chromatography and storage.
With the exception of 3p, the formation of -substituted vinyl
selenones occurred in good yields. Interestingly, the oxidation of
diphenyl selenide gave 3q in 80% yield.
slightly lower than those observed for alkyl aryl selenones (980-
1040 ppm).[3] are compatible with shielding effects due to
conjugation. The presence in the IR spectrum of two strong
absorptions around 930 and 880 cm-1, diagnostic for the
asymmetric and symmetric Se=O stretching frequencies,
respectively, completed the characterization.[10d,21]
Conclusions
In conclusion, the development of simple methods for the
preparation of synthetically[10-14] and biologically[22] useful
selenones is desirable. Our method expands the use of Oxone
to the synthesis of vinyl selenones providing a convenient
alternative in respect to the conventional procedure with
peroxyacids. Other advantages consist in easy handling, clean
reactions, no organic wastes derived from oxidant, easy work up,
and good yields. The development of a practical synthesis of
vinyl selenones should trigger further advances in the chemistry
of this interesting class of organoselenium compounds.
The scale up of the reaction was attempted at a 1g scale on 1l.
The desired selenone 3l was isolated in 68% yield.
Finally, considering the few information about 77Se NMR
resonance of selenones, a set of data have been collected for
their characterization. NMR spectra gave chemical shift values
around 960 ppm, shifted at lower magnetic fields respect to
those reported for the corresponding selenoxides (resonance
range: 812-941 ppm).[19] The deshielding is related with the
decreased electron density around the selenium atom. Values
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a white solid (m.p. 87-89°C) in 83% yield. 1H NMR (400 MHz, CDCl3,
25 °C, TMS): δ = 8.04 (d, J = 7.5 Hz, 2H), 7.92 (d, J = 15.6 Hz, 1H), 7.75-
7.65 (m, 2H), 7.56-7.43 (m, 6H), 7.19 (d, J = 15.6 Hz, 1H). 13C NMR (100
MHz, CDCl3): δ = 145.3, 142.0, 134.1, 131.8, 131.5, 130.2 (2C), 129.2
(2C), 128.7 (2C), 127.3, 126.8 (2C). 77Se NMR (76.27 MHz, CDCl3,
25°C): δ = 964. FT-IR (KBr): νmax 938.0, 878.4 cm-1 (Se=O stretching).
HRMS (ESI-TOF) m/z: [M+H]+calcd for C14H13O2Se 293.0080; found:
293.0086.
Experimental Section
Materials and methods
Commercial reagents and solvents were purchased from Sigma Aldrich,
Alfa Aesar or VWR International and used without further purifications.
According to literature procedures[23] the starting vinyl selenides 1a-f
were prepared by nucleophilic vinylic substitution of commercially or
easily available vinyl bromides or by selenodecarboxylation of cinnamic
acids. The vinyl selenides 1g-h were synthesized from the corresponding
alkenes by a sequence of selenobromination and dehydrobromination
with LDA.[24] The selenides 1i,n-o were prepared by reduction with
DIBAL-H of the corresponding alkynyl selenides.[25] Finally the vinyl
selenides 1j-m were obtained by treatment of diphenyl diselenide with an
excess of commercial vinyl magnesium bromides.[26] 1H NMR, 13C NMR
(acquired using a JMODXH pulsed sequence) and 77Se NMR spectra
were recorded respectively at 400, 100 and 76.7 MHz, with a Bruker
Avance-DRX 400 instrument. Chemical shifts (δ) are reported in ppm
(E)-2-(4-Chlorophenyl)vinyl phenyl selenone 3b [11a,12b]
The crude product was purified by chromatography (gradient elution:
from dichloromethane to dichloromethane/methanol 98:2) to afford 3b as
1
a white solid (m.p. 159-161°C) in 68% yield. H NMR (400 MHz, CDCl3,
25 °C, TMS): δ = 8.03 (d, J = 7.5 Hz, 2H), 7.87 (d, J = 15.3 Hz, 1H), 7.75-
7.64 (m, 3H), 7.48 (d, J = 8.3 Hz, 2H), 7.43 (d, J = 8.3 Hz, 2H), 7.16 (d, J
= 15.3 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ = 143.8, 141.9, 138.0,
134.2, 130.3 (2C), 130.0, 129.9 (2C), 129.6 (2C), 128.0, 126.8 (2C). 77Se
NMR (76.27 MHz, CDCl3, 25°C): δ = 963. FT-IR (KBr): νmax 932.9, 880.8
cm-1 (Se=O stretching). HRMS (ESI-TOF) m/z: [M+H]+ calcd for
C14H12ClO2Se 326.9691; found: 326.9696.
1
respecting residual solvent signals (CHCl3 7.26 ppm for H NMR, CDCl3
77.0 ppm for 13C NMR). For 77Se NMR the chemical shifts are relative to
external diphenyl diselenide in CDCl3 (δ = 463.0 ppm relative to Me2Se δ
= 0.0 ppm). Coupling constants J are expressed in Hz. The following
abbreviations are used to indicate the multiplicity: s, singlet; d, doublet; t,
triplet; q, quartet; (s = singlet, d = doublet, t = triplet, q = quartet, quint =
quintet, sex = sextet, m = multiplet;. FT-IR spectra were recorded with a
Jasco 410 spectrometer equipped with a diffuse reflectance accessory.
High resolution mass spectra (HRMS) were recorded on Agilent 6540-
UHD Accurate Mass QTOF LC/MS instrument or APEX IV 7T FTICR.
The peaks arising from the selenium–80 isotope are given. The melting
points are uncorrected. Thin layer chromatography (TLC) was performed
in 60 F254 (Merck) silica gel supported on aluminium sheets. Reaction
products were purified by column chromatography on Merck 60 (70-230
mesh) silica gel.
(E)-2-(4-Methylphenyl)vinyl phenyl selenone 3c[11a,12b]
The crude product was purified by chromatography (eluent:
dichloromethane) to afford 3c as a white solid (m.p. 145-146 °C) in 64%
yield. 1H NMR (400 MHz, CDCl3, 25 °C, TMS): δ = 8.05-8.00 (m, 2H),
7.88 (d, J = 15.4 Hz, 1H), 7.75-7.63 (m, 3H), 7.44 (d, J = 8.0 Hz, 2H),
7.25 (d, J = 8.0 Hz, 2H), 7.13 (d, J = 15.4 Hz, 1H), 2.41 (s, 3H). 13C NMR
(100 MHz, CDCl3): δ = 145.3, 142.7, 142.2, 134.1, 130.2 (2C), 130.0 (2C),
128.8, 128.7 (2C), 126.8 (2C), 126.0, 21.6. 77Se NMR (76.27 MHz, CDCl3,
25°C): δ = 964. FT-IR (KBr): νmax 932.4, 877.4 cm-1 (Se=O stretching).
HRMS (ESI-TOF) m/z: [M+H]+calcd for C15H15O2Se 307.0237; found:
307.0243.
General procedure for the synthesis of selenones 3
(E)-2-(4-Methoxyphenyl)vinyl phenyl selenone 3d[11a,12b]
To the Oxone triple salt (2KHSO5 KHSO4 K2SO4, 2.2 equiv.) dissolved in
5 mL of H2O the vinyl selenides 1a-p or the Ph2Se 1q (1 equiv.) were
added. The reaction mixtures were vigorously stirred at 60 °C for 3-24
hours. Then, the reactions were cooled to room temperature and
extracted with ethyl acetate (3 x 5 mL). After drying with Na2SO4, the
organic extracts were filtered and evaporated under reduced pressure.
The crude mixtures were purified through a short plug of silica gel giving
access to the corresponding selenones 3. The vinyl selenoxide 2a was
recovered as a single product when 0.6 equivalents of Oxone were used
in the oxidation of 1a.
The crude product was purified by chromatography (eluent:
dichloromethane/methanol 99:1) to afford 3d as a brownish solid (m.p.
138-140 °C) in 53% yield. 1H NMR (400 MHz, CDCl3, 25 °C, TMS): δ =
8.04 (d, J = 7.6 Hz, 2H), 7.86 (d, J = 15.4 Hz, 1H), 7.74-7.64 (m, 3H),
7.50 (d, J = 7.5 Hz, 2H), 7.01 (d, J = 15.4 Hz, 1H), 6.96 (d, J = 7.8 Hz,
2H), 3.87 (s, 3H). 13C NMR (100 MHz, CDCl3): δ = 163.0, 145.4, 142.8,
134.4, 131.1 (2C), 130.6 (2C), 127.2 (2C), 124.7, 124.6, 115.1 (2C), 55.9.
77Se NMR (76.27 MHz, CDCl3, 25°C): δ = 965. FT-IR (KBr): νmax 934.8,
880.4 cm-1 (Se=O stretching). HRMS (ESI-TOF) m/z: [M+Na]+calcd for
C15H14NaO3Se 345.0005; found: 345.0016.
Phenyl (E)-phenyl vinyl selenoxide 2a [11q]
(E)-2-(2-Methylphenyl)vinylphenylselenone 3e[12b]
The crude product was purified by chromatography (gradient elution:
from dichloromethane to dichloromethane/methanol 98:2) to afford 2a as
a white solid (m.p. 100-101°C) in 72% yield. H NMR (400 MHz, CDCl3,
The crude product was purified by chromatography (eluent:
1
dichloromethane/methanol 99:1) to afford 3e as a white solid (m.p. 110-
1
25 °C, TMS): δ = 7.78-7.71 (m, 2H), 7.54-7.42 (m, 6H), 7.38-7.32 (m, 3H),
7.09 (d, J = 15.6 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ = 141.3, 138.7,
133.6, 131.4, 130.0, 129 9, 129.8 (2C), 128.8 (2C), 127.7 (2C), 126.3
(2C). 77Se NMR (76.27 MHz, CDCl3, 25°C): δ = 853. FT-IR (KBr): νmax
972.0 cm-1 (Se=O stretching). HRMS (ESI-TOF) m/z: [M+H]+calcd for
C14H13OSe 277.0132; found: 277.0121.
112 °C) in 86% yield. H NMR (400 MHz, CDCl3, 25 °C, TMS): δ = 8.19
(d, J = 15.3 Hz, 1H), 8.05 (d, J = 7.5 Hz, 2H), 7.75-7.66 (m, 3H), 7.51 (d,
J = 7.5 Hz, 1H), 7.37 (t, J = 7.2 Hz, 1H), 7.29-7.24 (m, 2H), 7.11 (d, J =
15.3 Hz, 1H), 2.50 (s, 3H). 13C NMR (100 MHz, CDCl3): δ = 143.1, 142.2,
138.5, 134.1, 131.6, 131.2, 130.6, 130.2 (2C), 128.3, 1271, 126.9 (2C),
126.6, 19.8. 77Se NMR (76.27 MHz, CDCl3, 25°C): δ = 964. FT-IR (KBr):
νmax 936.3, 879.4 cm-1. HRMS (ESI-TOF) m/z: [M+Na]+calcd for
C15H14NaO2Se 329.0056; found: 329.0058.
Phenyl (E)-phenyl vinyl selenone 3a [11q]
(1E)-Oct-1-en-1-yl phenyl selenone 3g[12b]
The crude product was purified by chromatography (gradient elution:
from dichloromethane to dichloromethane/methanol 99:1) to afford 3a as
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The crude product was purified by chromatography (eluent:
981, 928, 882 cm−1 (Se=O stretching). HRMS (ESI-TOF) m/z: [M+Na]+
calcd for C8H8NaO2Se 238.9587; found: 238.9586.
dichloromethane/methanol 99:1) to afford 3g as a yellow oil in 89% yield
1
and 95:5 E/Z ratio. E isomer: H NMR (400 MHz, CDCl3, 25 °C, TMS): δ
= 8.01-7.85 (m, 2H), 7.75-7.52 (m, 3H), 7.16 (td, J = 6.6, 15.1 Hz, 1H, ),
6.61 (d, J = 15.1 Hz, 1H), 2.37-2.26 (m, 2H), 1.54-1.05 (m, 8H), 0.84 (s,
3H). 13C NMR (100 MHz, CDCl3): δ = 150.5, 141.9, 134.0, 130.1 (2C),
129.7, 126.7 (2C), 32.1, 31.3, 28.6, 27.2, 22.3, 13.9. 77Se NMR (76.27
MHz, CDCl3, 25°C): δ = 961. FT-IR (KBr): νmax 938.7, 882.8 cm-1. HRMS
(ESI-TOF) m/z: [M+Na]+ calcd for C14H20NaO2Se 323.0526; found:
323.0538.
4-Chlorophenyl vinyl selenone 3m
The crude product was purified by chromatography (gradient elution:
from dichloromethane to dichloromethane/methanol 98:2) to afford 3m as
a pale oil in 83% yield. 1H NMR (400 MHz, CDCl3, 25 °C, TMS): δ = 7.87
(d, J = 8.4 Hz, 2H), 7.59 (d, J = 8.4 Hz, 2H), 7.03 (dd, J = 9.0, 16.4 Hz,
1H), 6.71 (dd, J = 2.1, 16.4 Hz, 1H), 6.47 (dd, J = 2.1, 9.0 Hz, 1H). 13C
NMR (100 MHz, CDCl3): δ=141.1, 139.2, 138.5, 131.7, 130.7 (2C), 128.4
(2C). 77Se NMR (76.27 MHz, CDCl3, 25 °C): δ = 960. FT-IR (KBr): νmax
941.6, 883.7 cm−1 (Se=O stretching). HRMS (ESI-TOF) m/z: [M+H]+
calcd for C8H8ClO2Se 250.9378; found: 250.9370.
(E)-Hex-1-en-1yl phenyl selenone 3h[11o]
The crude product was purified by chromatography (gradient elution:
from light petroleum/ethyl acetate 70:30 to light petroleum/ethyl acetate
50:50) to afford 3h as a yellow oil in 67% yield. 1H NMR (400 MHz,
CDCl3, 25 °C, TMS): δ = 8.0-7.93 (m, 2H), 7.74-7.62 (m, 3H), 7.21 (td, J
= 7.0, 15.1 Hz, 1H), 6.63 (d, J = 15.1 Hz, 1H), 2.37 (q, J = 7.0 Hz, 2H),
1.51 (quin, J = 7.0 Hz, 2H), 1.37 (sex, J = 7.3 Hz, 2H), 0.92 (t, J = 7.3,
3H). 13C NMR (100 MHz, CDCl3): δ = 150.5, 141.9, 134.0, 130.2 (2C),
129.6, 126.8 (2C), 31.8, 29.4, 22.1, 13.7. 77Se NMR (76.27 MHz, CDCl3,
25 °C): δ = 961. FT-IR (KBr): νmax 937.7, 882.3 cm-1. HRMS (ESI-TOF)
m/z: [M+Na]+calcd for C12H16NaO2Se 295.0213; found: 295.0224.
Isopropenyl phenyl selenone 3n
The crude product was purified by chromatography (eluent:
dichloromethane/methanol 98:2) to afford 3m as a pale oil in 50% yield.
1H NMR (400 MHz, CDCl3, 25 °C, TMS): δ = 7.95-7.88 (m, 2H), 7.72-
7.61 (m, 3H), 6.40-6.37 (m, 1H), 6.02-5.97 (m, 1H), 2.20-2.15 (m, 3H).
13C NMR (100 MHz, CDCl3, 25°C): δ = 149.6, 139.8, 134.2, 130.3 (2C),
127.2 (2C), 124.9, 16.4. 77Se NMR (76.27 MHz, CDCl3, 25°C): δ = 976.
FT-IR (KBr): νmax 938.2, 881.3 cm-1 (Se=O stretching). HRMS (ESI-TOF)
m/z: [M+H]+calcd for C9H10NaO2Se 252.9743; found: 252.9739.
(Z)-Hex-1-en-1yl phenyl selenone 3i
The crude product was purified by chromatography (gradient elution:
from light petroleum ether/ethyl acetate 70:30 to light petroleum
ether/ethyl acetate 50:50) to afford 3i as a pale oil in 45% yield. H NMR
1-Butylvinyl phenyl selenone 3o
1
The crude product was purified by chromatography (eluent:
dichloromethane/methanol 99:1) to afford 3n as a yellow oil in 60% yield.
1H NMR (400 MHz, CDCl3, 25 °C, TMS): δ = 7.99-7.94 (m, 2H), 7.74-
7.60 (m, 3H), 6.50-6.35 (m, 1H), 6.05-5.95 (m, 1H), 2.54-2.40 (m, 2H),
1.53 (quin, J = 7.4 Hz, 2H), 1.29 (sex, J = 7.4 Hz, 2H), 0.85 (t, J = 7.4 Hz,
3H). 13C NMR (100 MHz, CDCl3): δ = 154.6, 140.7, 134.1, 130.2 (2C),
127.2 (2C), 123.4, 29.6, 29.2, 21.8, 13.5. 77Se NMR (76.27 MHz, CDCl3,
25°C): δ = 977. FT-IR (KBr): νmax 939.6, 881.8 cm-1 (Se=O stretching).
HRMS (ESI-TOF) m/z: [M+Na]+calcd for C12H16NaO2Se 295.0213; found:
295.0207.
(400 MHz, CDCl3, 25 °C, TMS): δ = 8.0-7.93 (m, 2H), 7.71-7.60 (m, 3H),
6.66 (td, J = 7.6, 9.3 Hz, 1H), 6.56 (d, J = 9.2 Hz, 1H), 2.67 (q, J = 7.6 Hz,
2H), 1.40-1.23 (m, 4H), 0.84 (t, J = 7.3 Hz, 3H). 13C NMR (100 MHz,
CDCl3): δ = 150.7, 143.6, 134.0, 131.6, 130.1 (2C), 126.5 (2C), 30.4,
29.2, 22.1, 13.6. 77Se NMR (76.27 MHz, CDCl3, 25°C): δ = 962. FT-IR
(KBr): νmax 937.7, 883.2 cm-1 (Se=O stretching). HRMS (ESI-TOF) m/z:
[M+Na]+calcd for C12H16NaO2Se 295.0213; found: 295.0222.
Phenyl (1E/Z)-prop-1-en-1-yl selenone 3j[11f]
Diphenyl selenone 3q[7,27]
The crude product was purified by chromatography (gradient elution:
from dichloromethane to dichloromethane/methanol 99:1) to afford 3j
(yellow oil) as a 50:50 mixture of E:Z isomers in 64% yield.
The crude product was purified by chromatography (eluent:
dichloromethane/methanol 99:1) to afford 3q as a colourless solid (m.p.
141-142 °C) in 80% yield. 1H NMR (400 MHz, CDCl3, 25 °C, TMS): δ =
8.02-7.96 (m, 4H), 7.69-7.58 (m, 6H). 13C NMR (100 MHz, CDCl3): δ =
142.4 (2C), 134.2(2C), 130.3 (4C), 126.8 (4C). 77Se NMR (76.27 MHz,
CDCl3, 25°C): δ = 966. FT-IR (KBr): νmax 936.7, 880.4 cm-1 (Se=O
stretching).
E isomer:1H NMR (400 MHz, CDCl3, 25 °C, TMS): δ = 7.97-7.91 (m, 2H),
7.74-7.57 (m, 3H), 7.17 (qd, J = 7.0, 15.0 Hz, 1H), 6.65 (qd, J = 1.4, 15.0
Hz, 1H), 2.03 (dd, J = 1.4, 7.0 Hz, 3H). 13C NMR (100 MHz, CDCl3): δ =
145.9, 141.7, 134.1 (2C), 131.0, 130.2 (2C), 126.7, 17.9. 77Se NMR
(76.27 MHz, CDCl3, 25°C): δ = 960. Z isomer: 1H NMR (400 MHz, CDCl3,
25 °C, TMS): δ 8.03–7.96 (m, 2H), 7.74-7.57 (m, 3H), 6.77 (qd, J = 7.3,
9.3 Hz, 1H), 6.57 (qd, J = 1.4, 9.3 Hz, 1H), 2.25 (dd, J = 1.4, 7.3 Hz, 3H).
13C NMR (100 MHz, CDCl3, 25°C): δ = 145.8, 143.1, 134.1 (2C), 132.3,
130.2 (2C), 126.5, 15.5. 77Se NMR (76.27 MHz, CDCl3, 25°C): δ = 962.
FT-IR (KBr): νmax 937.7, 883.2 cm-1 (Se=O stretching).
2-methoxy-2-phenylethyl phenyl selenone 4a[11r]
The crude product was purified by chromatography (eluent:
dichloromethane/methanol 98:2) to afford 4a as a white solid (m.p. 162-
1
165 °C) in 50% yield. H NMR (400 MHz, CDCl3, 25 °C, TMS): δ = 8.06
Phenyl vinyl selenone 3l[11b]
(d, J = 7.5 Hz, 2H), 7.75-7.60 (m, 3H), 7.50-7.10 (m, 5H), 4.97 (dd, J =
2.2, 11.2 Hz, 1H), 3.92 (dd, J = 11.2, 12.8 Hz, 1H), 3.65 (dd, J = 2.2, 12.8
Hz, 2H), 3.18 (s, 3H). 13C NMR (100 MHz, CDCl3): δ = 143.8, 137.0,
133.9, 129.8 (2C), 129.1 (3C), 127.1 (2C), 126.5 (2C), 77.1, 66.8, 56.5.
77Se NMR (76.27 MHz, CDCl3, 25°C): δ = 988. FT-IR (KBr): νmax 926.2,
884.2 cm-1 (Se=O stretching). HRMS (ESI-TOF) m/z: [M+Na]+ calcd for
C15H16NaO3Se 347.0162; found: 347.0170.
The crude product was purified by chromatography (gradient elution:
from dichloromethane to dichloromethane/methanol 98:2) to afford 3l as
a white solid (m.p. 97-102 °C) in 70% yield. 1H NMR (400 MHz, CDCl3,
25 °C, TMS): δ = 8.0–7.91 (m, 2H), 7.77–7.59 (m, 3H), 7.0 (dd, J = 9.0,
16.5 Hz, 1H), 6.72 (d, J = 16.5 Hz, 1H), 6.46 (d, J = 9.0 Hz, 1H). 13C
NMR (100 MHz, CDCl3): δ=141.0, 138.8, 134.4, 131.3, 130.3 (2C), 126.9
(2C). 77Se NMR (76.27 MHz, CDCl3, 25 °C): δ = 961. FT-IR (KBr): νmax
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10.1002/ejoc.201800498
European Journal of Organic Chemistry
FULL PAPER
Org. Biomol. Chem. 2016, 14, 2015-2024; (i) M.Palomba, E.Vinti, F.
Marini, C. Santi, L. Bagnoli, Tetrahedron 2016, 72, 7059-7064. (l) T.
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Acknowledgements
University of Perugia “Fondo Ricerca di Base 2017“ and
Consorzio CINMPIS
-
Bari (Consorzio Interuniversitario
Nazionale di Metodologie e Processi Innovativi di Sintesi) are
gratefully acknowledged. The research was undertaken as part
of the scientific activity of the international multidisciplinary “SeS
Redox and Catalysis network.
Keywords: Oxone • Selenium • Oxidation • Water •
Organochalcogen Compounds
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European Journal of Organic Chemistry
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A simple and practical procedure for
the oxidation of vinyl selenides to the
corresponding selenones using Oxone
in water at 60 °C has been reported.
Key Topic Organoselenium chemistry
Martina Palomba, Francesco Trappetti,
Luana Bagnoli, Claudio Santi and
Francesca Marini*
Page No. – Page No.
Title Oxone mediated oxidation of
vinyl selenides in water
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Key Topic*
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