Synthesis of selenol esters from diorganyl diselenides and acyl chlorides under solvent-free conditions and microwave irradiation

Article abstract of DOI:10.1039/c1gc16243h

Herein, we report an efficient, quick and eco-friendly new method for the synthesis of a variety of selenol esters. This novel solvent-free methodology gave good to excellent isolated yields of desired products after just 2 min under microwave irradiation

Full text of DOI:10.1039/c1gc16243h

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PAPER
Synthesis of selenol esters from diorganyl diselenides and acyl chlorides
under solvent-free conditions and microwave irradiation†
Marcelo Godoi,a Eduardo W. Ricardo,a Giancarlo V. Botteselle,a Fabio Z. Galetto,a,b Juliano B. Azeredoa
and Antonio L. Braga*a
Received 6th October 2011, Accepted 18th November 2011
DOI: 10.1039/c1gc16243h
Herein, we report an efficient, quick and eco-friendly new method for the synthesis of a variety of
selenol esters. This novel solvent-free methodology gave good to excellent isolated yields of desired
products after just 2 min under microwave irradiation. Furthermore, by using the same green
approach, we were also able to synthesize selenocarbonates bearing interesting functionalities.
special attention for the synthesis of new molecular materials,
Introduction
including superconducting materials and liquid crystals.15 Fur-
Organoselenium compounds have been gaining increasing atten-
thermore, applications of selenol esters have been expanded to
tion in recent years, mainly due to their properties as antioxidant
the synthesis of proteins by chemical ligation of chalcogenol
and antitumor agents, apoptosis inducers and in the effective
esters,16 to the synthesis of substrates which undergo facile and
chemoprevention of cancer in a variety of organs.1,2
efficient radical decarbonylation, as well as to the synthesis of
Moreover, this class of compounds has become an attractive
the natural alkaloid.17
synthetic target in chemo-, regio- and stereoselective reactions.3,4
Although several methods were reported in the past,18 new
Notably in this context, organoselenium compounds have been
methods for the synthesis of selenol esters have still been
used as chiral catalysts in asymmetric catalysis,5,6 as well as
described. In this context, these compounds have been prepared
electrophilic, nucleophilic and radical species in cross-coupling
under different reaction conditions, for instance, from aldehydes
reactions.7
using both i-Bu2AlSeR19 and SeCO,20 from anhydride using ron-
The most convenient methodologies for the incorporation
galite/base system.21 Moreover, employing selenoacetylenes22
of selenium into organic compounds generally involve the
as selenium source and by coupling of aryl iodides with
preparation of selenolate anions, which can be generated via
reductive cleavage of Se–Se bonds. The most commonly used
protocols for generating selenolates in situ have employed several
reducing agents, such as NaBH4, LiAlH4 and other expensive
metal sources such as La, In, Yb, Sm, etc.8,9 Thus, research
aimed at improving these transformations is currently of great
interest. In particular, studies on the use of Zn dust for the
cleavage of diselenides have received special attention due to the
unique properties of this material, including easy manipulation
and better stability in air compared to other metals.10,11
CO and PhSeSnBu3 catalyzed by Pd.23 However, the vast
majority of methodologies reported have used acyl chlorides
with nucleophilic species of selenium involving reagents such
as Hg(SePh)2,24 PhSeSiMe325 and PhSeSnBu3/Pd,26 or reductive
cleavage of diselenides with indium,27 indium(I) iodide28 and
magnesium.29 Furthermore, the reductive coupling of diselenide
and acyl chloride in an Rh/H2 system has also been reported.30
All of the methods cited above are detailed in Fig. 1.
Despite the variety of methodologies described to date, it
is well recognized that most of the protocols shown in Fig. 1
have their respective drawbacks, such as air reactivity of some
selenium compounds, use of toxic and carcinogenic solvents,
and long reaction time. In addition, some procedures which
do not require the use of an inert atmosphere, such as the
synthesis of selenol esters from selenoacetylenes, also have their
own limitations since these compounds are not readily available.
Alternatively, in order to minimize these limitations concern-
ing the synthesis of selenol esters, we have recently reported
new methods employing the use of ionic liquids as eco-
friendly solvents in different reaction systems.31 However, the
development of new methodologies to carry out the preparation
of selenol esters under mild reaction conditions, open to the
Selenol esters have been shown to be of great importance as
intermediates in several organic transformations.12 For instance,
these kinds of compounds have been successfully employed as
precursors of acyl radicals13 and anions14 and also have attracted
aDepartamento de Qu´ımica, Universidade Federal de Santa Catarina,
Floriano´polis, SC, Brazil. E-mail: albraga@qmc.ufsc.br; Fax: +55-48
3721 6427; Tel: +55-48 3721 6844
bDepartamento de Qu´ımica, Universidade Federal de Santa Maria, Santa
Maria, RS, Brazil; Fax: +55-55 3220 8998; Tel: +55-55 3220 8761
† Electronic supplementary information (ESI) available: Detailed exper-
imental procedures, NMR spectra of all isolated compounds. See DOI:
10.1039/c1gc16243h
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Table 1 Optimization of the reaction conditionsa
MW
power (W)
Time
(min)
Yield
(%)b
Entry
T (◦C)
1
2
3
4
5
6
7
8
100
100
100
100
100
100
100
150
50
80
80
80
80
80
50
130
80
80
80
0.5
1.0
2.0
5.0
2.0
2.0
2.0
2.0
2.0
90.0
61
72
88
90
88c
63
91
88
40
67d
9
10
—
a Reaction conditions: benzoyl chloride (0.5 mmol), diphenyl diselenide
(0.25 mmol), Zn dust (0.25 mmol), MW. b Isolated yields. c Reaction was
carried out under argon atmosphere. d Conventional heating.
reaction was carried out for 2 min the corresponding product
was enhanced, in this case to 88% yield (entry 3). On further
extension of the irradiation time, no significant change in the
yield was observed (Table 1, entry 4).
Furthermore, it was observed in this study that the inert
atmosphere did not influence the reaction, since we obtained
the desired product in the same yield compared with open
atmosphere (entry 3 vs. 5).
On the other hand, the reaction temperature proved to have a
great influence on the yield values (entries 3, 6 and 7). Screening
this reaction parameter revealed that a value of 80 ◦C wa◦s most
appropriate, since on decreasing the temperature to 50 C the
desired selenol ester was obtained in lower yield, whilst on
increasing the temperature from 80 to 130 ◦C no significant
change in the yield was observed (entry 3 vs. 7).
Fig. 1 General methodologies for the synthesis of selenol esters.
air, employing stable and non-hazardous starting materials and
short reaction time coupled with neat conditions, is still highly
desirable.
On the other hand, microwave (MW) irradiation has provided
higher yields, avoiding the synthesis of side products and
allowing milder conditions and shorter reaction times in several
transformations.32 From an environmental point of view, the
use of microwave irradiation associated with neat conditions
has been described and is emerging as an environmentally
benign alternative.33 Nonetheless, this irradiation source has
not been widely employed in organoselenium chemistry and
studies exploring a combination of microwaves and solvent-free
conditions are rare in this area.34
Focusing on the influence of the microwave irradiation on
the system we carried out the reaction with different levels of
microwave power (50–150 W). An increase in the power from 100
to 150 W did not affect the reaction since the desired product 3a
was obtained in the same yield (entry 8). However, on decreasing
the power to 50 W the yield decreased considerably (entry 9).
Therefore, this optimization of the irradiation power showed
that 100 W was the best choice for the synthesis of selenol
esters (entry 3). Moreover, we also carried out the reaction
under conventional heating and even after a long reaction time
only 67% yield of the desired product was achieved (entry 10).
Thus, these results indicated that the reaction performed under
microwave irradiation has significant advantages compared to
conventional heating, since the reaction time was reduced and
the desired product was obtained in better yield.
Thus, in connection with our continuing interest in organose-
lenium chemistry using eco-friendly conditions,31,35 herein we
describe a novel method for the synthesis of selenol esters in the
absence of solvent, under microwave irradiation in a very short
reaction time (Scheme 1).
Scheme 1 Synthesis of selenol esters.
Results and discussion
In order to optimize our protocol, we performed the reaction
using benzoyl chloride, diphenyl diselenide and zinc dust in
the absence of solvent with an irradiation power of 100 W
(Table 1). Firstly, the reaction was carried out for only 0.5 min,
affording the desired product in 61% yield (entry 1). However,
on increasing the reaction time to 1 min, the selenol ester 3a
was obtained with 72% yield (entry 2). Similarly, when the
Once we had established the best conditions, we then exam-
ined the scope of the reaction (Table 2). At first, a variety of
diorganyl diselenides were reacted with benzoyl chloride in order
to synthesize different selenol esters (entries 1–6).
The electronic effects of substituents in the aryl diselenides
were evaluated and showed a remarkable effect on the reaction.
For instance, when diselenides containing withdrawing groups
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Table 2 Synthesis of selenol esters with a variety of diselenidesa
Table 3 Synthesis of several selenol estersa
Yield (%)b
90
Entry
1
R1
Product
Yield (%)b
80
Entry
1
R
Product
p-MePh, 1b
p-ClPh, 2b
2
3
p-BrPh, 1c
o-ClPh, 1d
95
64
2
3
4
p-MePh, 2c
p-MeOPh, 2d
o-ClPh, 2e
66
61
92
4
5
Me, 1e
86
40
t-Bu, 1f
5
o-MePh, 2f
70
6
ClC4H8, 1g
41
6
7
Bn, 2g
Et, 2h
71
70
a Reaction conditions: acyl chloride (0.5 mmol), diorganyl diselenide
(0.25 mmol), Zn dust (0.25 mmol), MW (100 W), 80 ◦C, 2 min. b Isolated
yields.
a Reaction conditions: acyl chloride (0.5 mmol), diorganyl diselenide
(0.25 mmol), Zn dust (0.25 mmol), MW (100 W), 80 ◦C, 2 min. b Isolated
yields.
used the corresponding product was obtained with 80% yield
(entry 1).
Notably, when p-bromo benzoyl chloride was employed as
the acyl source the yield increased to 95% (entry 2). However,
benzoic acid chloride with a halide in the ortho position did not
provide an active substrate under the same reaction conditions,
affording the desired product in only 64% yield (entry 3).
Some aliphatic acyl chlorides were also used in order to
synthesize alkylic selenol esters (entries 4–6). It was noted that
when the acyl chloride 1e was used the corresponding product
was achieved with 86% yield (entry 4).
However, the aliphatic acyl chlorides which were sterically
hindered proved to be less reactive substrates in the present
methodology. Thus, using either 2,2-dimethylpropionyl chloride
or 3-chloro-2,2-dimethylpropanoyl chloride afforded the corre-
sponding products 3n and 3o in lower yields (entries 5 and 6).
It is well known that selenium-containing protecting groups
make these reagents particularly valuable for efficient ap-
plication in palladium-catalyzed decarboxylation.37 Thus, we
also attempted to synthesize different selenocarbonates bearing
interesting functionalities by using the same methodology.
Gratifyingly, the corresponding products were obtained with
satisfactory yields, as depicted in Fig. 2.
attached to the aromatic ring were used, a significant improve-
ment in the yield values was observed and the desired products
were achieved in 90% and 92% yields, respectively (entries 1
and 4). Meanwhile, by using either a weak or a strong electron
donating group, the corresponding products were obtained in
lower yields (entries 2, 3 and 5). These considerable decreases in
the yield values may be explained by the stronger Se–Se bond of
electron-rich aryl diselenides.
It is well recognized that diaryl diselenides are more reactive
than aliphatic ones and are also much more easily cleaved.36
Applying the same methodology, we prepared the selenol
ester starting from aliphatic diselenides. Using both dibenzyl
diselenide and diethyl diselenide as a source of selenolate anions,
the corresponding compounds 3f and 3g were obtained in good
yields (entries 6 and 7).
In our reaction system we also investigated the combination
of a range of structurally diverse acid chlorides with diphenyl
diselenide (Table 3). When compound 1b, with a soft electron-
donor group in the para position of the aromatic ring, was
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esters by carrying out all reactions in the absence of solvent,
open to the air, with a short reaction time and under microwave
irradiation.
We believe that the chemistry described fulfils most of the aims
of “green chemistry” and may represent an environmentally-
benign alternative for the synthesis of different types of selenol
esters, including selenocarbonates ,which can be used either
as protecting groups for organoselenium compounds or in the
synthesis of selenoamino acids. Intensive research in this area
remains in progress in our laboratory.
Experimental section
Detailed experimental procedures, H and 13C NMR spectra
for all compounds are available in the supporting information,
ESI†.
1
Fig. 2 Synthesis of selenocarbonates.
Interestingly, as described previously by our group,27 the
FMOC-modified substrate 1j is an efficient protecting group
for organic selenium compounds and can also be extended to
the synthesis of seleno amino acids.
Acknowledgements
We are grateful to CAPES, CNPq (INCT-Cata´lise)andFAPESC
for financial support. CAPES is also acknowledged for the
doctorate fellowship received by M. G.
It is well established that metallic zinc can be inserted into
a diselenide bond, and an RSeZnSeR complex is formed in
the reaction medium.9 A plausible pathway for the synthesis of
selenol esters is illustrated in Scheme 2. We assumed that initially
the diselenide bridge is rapidly cleaved by Zn dust, affording
the complex di(organylselenyl)zinc 4, which reacts with acyl
chloride furnishing the product 3 and RSeZnCl. Subsequently,
compound 5, which is a versatile reagent according to Santi
et al.,38 undergoes a nucleophilic attack on another equivalent of
acyl chloride 1, giving another equivalent of the desired selenol
ester.
Notes and references
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to excellent yields. Moreover, this procedure is highly efficient
and environmentally benign, allowing the synthesis of selenol
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460 | Green Chem., 2012, 14, 456–460
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