Regioselective Ring-Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]-FeIII Triflate Complex

Article abstract of DOI:10.1002/cssc.201901329

A Fe^III-triflate complex, bearing a bis-thioether-di-phenolate [OSSO]-type ligand, was discovered to promote the ring-opening of glycidol with alcohols under mild reaction conditions (0.05 mol % catalyst and 80 °C). The reaction proceeded with high activity (initial turnover frequency of 1680 h^?1 for EtOH) and selectivity (>95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84–96 % yield of the non-symmetric regioisomer). This synthetic approach allows the conversion of a glycerol-derived platform molecule (i.e., glycidol) to high-value-added products by using an Earth-crust abundant metal-based catalyst.

Full text of DOI:10.1002/cssc.201901329

Accepted Article
Title: Regioselective Ring Opening of Glycidol to Monoalkyl Glyceryl
Ethers Promoted by an [OSSO]-FeIII Triflate Complex
Authors: Francesco Della Monica, Maria Ricciardi, Antonio Proto,
Raffaele Cucciniello, and Carmine Capacchione
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ChemSusChem
10.1002/cssc.201901329
COMMUNICATION
Regioselective Ring Opening of Glycidol to Monoalkyl Glyceryl
Ethers Promoted by an [OSSO]-Fe(III) Triflate Complex
†
[a]
† [a]
[a] [a]
Antonio Proto, Raffaele Cucciniello* and Carmine
Francesco Della Monica,
Maria Ricciardi,
[a]
Capacchione*
Abstract: A new Fe(III)-triflate complex, bearing a bis-thioether-di-
phenolate [OSSO]-type ligand, is reported to promote the ring-
opening of glycidol with alcohols under mild reaction conditions (0.05
mol% of catalyst and 80 °C). The reaction proceeds with high activity
-
1
(
(
(
initial turnover frequency of 1680 h for ethanol) and selectivity
>95%) toward the formation of twelve monoalkyl glyceryl ethers
MAGEs) in a regioselective fashion (84-96% of non-symmetric
regioisomer). This synthetic approach allows the conversion of a
glycerol-derived platform molecule, such as glycidol, to high value-
added products using an Earth-crust abundant metal-based catalyst.
The regioselective ring-opening of epoxides has been
1–7]
[
intensively investigated during the last two decades.
In
particular, since the discovery of many useful synthetic
strategies that have given access to a wide variety of chiral
epoxides, this reaction became an important entry in the toolbox
of organic synthesis for the obtaining of enantiopure
[
8–11]
molecules.
Among oxiranes, glycidol (GLY) has attracted
much attention, not only because can act as corner-stone for the
synthesis of more complex molecules, but also because the
presence of
[12–14]
reactivity.
a
hydroxyl group profoundly influence its
We have recently shown that glycidol can be
Scheme 1. Comparison between previously reported homogeneous catalytic
systems for the preparation of MAGEs from GLY (top), and the [OSSO]-Fe(III)
triflate complex 1 proposed in this work.
conveniently obtained as value-added product from bio-based
epichlorohydrin (ECH) production plants (EPICEROL® process,
[
15]
Solvay)
enhancing the environmental sustainability of the
entire ECH chain and interest towards GLY conversion to
[18–20]
[16]
[17]
Indeed, Pires and colleagues reported the selective preparation
of MAGEs from GLY and alcohols in the presence of 20% in
moles of KOH as basic homogeneous catalyst, with good
valuable chemicals
[21,22]
(polymers,
drugs,
diols,
[12,13]
solketal
and organic carbonates
). Among the possible
products that can be obtained by nucleophilic ring-opening of
GLY, monoalkyl glyceryl ethers (MAGEs) are a relevant class of
molecules, not only because they represent one of the most
successful example of glycerol valorisation, but also because
[
26]
yields.
reaction media to improve the reaction selectivity to MAGEs
inhibiting oligomerization side-reaction. However, the
Herein, glycidol was added drop-by-drop to the
[23]
regioselectivity strongly depended from the alcoholic substrate,
ranging from 30 to 93%. Recently, we have shown that simple
Lewis acid catalysts, such as Al, Bi and Fe(III) triflates, catalyse
the same process more efficiently, under mild reaction
they find application in many significant industrial areas.
Unfortunately, the direct synthesis of MAGEs form GLY is
affected by many drawbacks (high temperature, low chemo- and
regioselectivity, high catalyst loading) rendering this synthetic
[
29]
[
24,25]
conditions with good chemoselectivity and wider scope.
Moreover, the reaction showed certain degree of
strategy inconvenient for industrial implementation.
Nevertheless, such synthesis was recently accomplished both
a
[
26]
regioselectivity (66-78%) to the formation of non-symmetric
regioisomer A with respect to the symmetric regioisomer B
(Scheme 1), suggesting that the nucleophilic attack takes place
preferably at the less substituted carbon atom (C3) of GLY. In
order to increase the regioselectivity of this reaction, a possible
approach is to wrap the metal centre in a sterically encumbered
ligand in order to favour the nucleophilic attack to the C3
position. This synthetic strategy is extremely important to obtain
MAGEs without difficult and expensive purification procedures
between A and B regioisomers, since they show very similar
chemical-physics properties.
under basic conditions,
or in the presence of acidic
heterogeneous (i.e. Amberlyst® IRA-400 and Nafion
[29,30]
[
27,28]
NR50®)
and homogenous (metal triflates)
catalytic
‡
systems. Since the first efforts both synthetic strategies have
been optimized in the tentative to milder the reaction conditions
and enlarge substrates scope (Scheme 1).
[a]
Dr. F. Della Monica, Dr. M. Ricciardi, Prof. A. Proto, Dr. R.
Cucciniello, Prof. Dr. C. Capacchione
Dipartimento di Chimica e Biologia “Adolfo Zambelli”
Università degli Studi di Salerno
With this target in mind we decided to use a new [OSSO]-Fe(III)
triflate complex 1 (Scheme 1), supported by a bis-thioether-di-
phenolate ligand, as catalyst for the ring opening reaction of
GLY with alcohols.
Via Giovanni Paolo II, 132 – 84084 (SA) Italy
E-mail: rcucciniello@unisa.it, ccapacchione@unisa.it
These authors contributed equally to this work.
†
Supporting information for this article is given via a link at the end of
the document.((Please delete this text if not appropriate))
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ChemSusChem
10.1002/cssc.201901329
COMMUNICATION
Figure 1. [OSSO]-Fe(III) chloride complexes 2-4.
Indeed, the use of [OSSO]-Fe(III) halide complexes for the
efficient activation of epoxides toward reaction with CO
2
producing cyclic and polycarbonates under mild conditions, was
[31,32]
recently reported by us.
In addition, iron is a low-cost, non-
toxic, Earth-crust abundant metal and the implementation of
[
catalytic protocols using this element are highly desirable.
33–40]
Initially, complexes 2-4 (Figure 1) have been tested in the
reaction of GLY with ethanol as benchmark. The reactions were
carried out under solventless condition, with 0.1 mol% of Fe and
in the presence of 9 equivalents of alcohol to avoid GLY
[
29]
oligomerization.
All the complexes were found to be active,
with the best result observed with complex 2, reaching a
conversion of 61% in 24 hours with 94% of selectivity toward
regioisomer A (compare entries 2-4, Table S2 in Supporting
Information). Since Fe(OTf)
29]
3
demonstrated to be much more
[
3
effective than FeCl ,
complex 1 has been prepared by
reaction of complex 2 with silver triflate (see Supporting
Information Figure S1), and was completely characterized by
elemental analysis, NMR Evans method, Fourier transform
infrared spectroscopy and FT-ion cyclotron resonance mass
spectrometry (see Supporting Information).
Under the same conditions used for 2-4, catalyst 1 was found to
be twenty times more active, reaching 88% of conversion in only
2
hours (entry 13, Table S2).
Encouraged by these results, complex 1 has been tested in the
reaction of GLY with ethanol as benchmark, with the purpose to
find the best reaction conditions. On using 0.1 mol% of Fe, the
catalyst was found to be active even at 30 °C (Figure 2a).
However, a strong enhancement of the catalytic activity was
observed at temperatures higher than 50 °C, reaching complete
conversion at 80 °C in 4.5 hours. To our delight, the reaction
proceeds with high selectivity toward monoethoxyglyceryl ethers
Figure 2. Effect of reaction temperature (a), catalyst loading (b) and reaction
time (c) on the reaction of GLY with EtOH. Reaction conditions: a) GLY = 3.0
mmol, EtOH = 27.0 mmol, 1 = 0.1 mol% with respect to GLY, time = 4.5 h; b)
GLY = 3.0 mmol, EtOH = 27.0 mmol, time = 2 h (5h for the point at 0.025
mol% of 1), temperature = 80 °C; c) GLY = 3.0 mmol, EtOH = 27.0 mmol, 1 =
0.05 mol% with respect to GLY, temperature = 80 °C. Selectivity to MAGEs
was always >95%. Carbon balance based on the carbon content in the
unconverted glycidol and in the desired products is systematically calculated
and is in all cases higher than 95%.
(
>95%), and high degree of regioselectivity, with 90% of
regioisomer A (Scheme 1). In addition, at this temperature, the
catalyst loading can be reduced from 0.1 to 0.05 mol% saving
catalytic activity and selectivity (Figure 2b), whereas in the
presence of 0.025 mol% of catalyst the conversion decreases to
Under these optimized reaction conditions, an initial turnover
-1
frequency (TOF) of 1680
h
was recorded. Notably, the
3
0% after 5 hours maintaining high regioselectivity in A (90%).
regioselectivity is almost constant during the whole course of
reaction.
Finally, the reaction was monitored during a period of 5 hours,
and the reaction profile is reported in Figure 2c.
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ChemSusChem
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COMMUNICATION
Table 1. Regioselective etherification of GLY with alcohols catalysed by
[
complex 1.
differences related with the substrates. All the reactions proceed
smoothly, with conversions similar to that obtained with the
EtOH using both short and long-chain alcohols.
a]
This result had not previously been reported with any catalytic
system wherein generally glycidol etherification to MAGEs
proceeds faster with short-chain alcohols. Notably, the reaction
proceeds faster in the case of iso-propanol and iso-butanol
(entries 7 and 9). The as-obtained MAGEs and the unreacted
alcohol can be simply separate at the end of the reaction owing
[
b]
[b]
-1 [c]
Entry
R
Time [h]
1
Conversion [%]
A/B
TOF [h ]
1
2
3
4
5
6
7
8
9
methyl
8
n.d.
160
8
[
d]
24
1
5
1
5
1
5
1
5
1
5
1
5
1
5
1
5
1
5
1
5
1
5
99
44
88
46
85
60
80
42
78
57
82
40
57
42
63
38
66
41
75
38
58
40
68
94/6
[43]
to the highly different boiling points among them. Complex 1 is
removed by adding 100 µL of distilled water to the reaction
medium and then filtering on celite. ICP-OES analyses confirm a
reduction of 95% of the iron content (from 43.4 to 2.2 mg/L, see
Supporting Information).
ethyl
90/10
89/11
90/10
88/12
93/7
880
352
920
340
1200
320
840
312
1140
328
800
228
840
252
760
264
820
300
760
232
800
272
n-propyl
iso-propyl
n-butyl
We verified this possibility, by using ethanol as nucleophile, and
monoethoxyglyceryl ether was quantitatively isolated by using a
rotary evaporator under reduced pressure (isolated yield of 97%
after 8 hours).
It is worth noting that methanol (entry 1) represents the only
exception, recording a conversion of only 8% in 1 hour. This
drawback could be reasonably ascribed to the higher acidity and
nucleophilicity of MeOH with respect to other alcohols. However,
reducing the reaction temperature from 80 to 40 °C, it is possible
to obtain complete conversion in 24 hours, with high selectivity
to A (94%). To test the robustness of complex 1, we investigated
the catalyst stability after completion of the reaction between
GLY and EtOH under optimized reaction conditions (Figure 3).
Experiments were performed by adding an extra amount of GLY
to the reaction medium, keeping a GLY/EtOH molar ratio of 9:1
in order to preserve the chemoselectivity of the reaction.
91/9
90/10
88/12
90/10
89/11
96/4
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
iso-butyl
tert-butyl
n-pentyl
iso-pentyl
n-octyl
95/5
87/13
89/11
88/12
90/10
88/12
92/8
iso-octyl
benzyl
91/9
90/10
84/16
88/12
[
a] Reaction conditions: GLY = 3.0 mmol (0.2 mL); alcohol = 27 mmol; 1 = 1.5 ∙
-
6
1
0
mol (0.05 mol%); temperature = 80 °C. [b] Determined by gas
chromatography. The selectivity toward the formation of MAGEs was always
-
1
-1
found to be >95%. [c] Turnover frequency: TOF = conversion ∙ mol
2
∙ time .
Figure 3. Stability test for catalyst 1 during the reaction of GLY with EtOH.
Reaction conditions at start: GLY = 15.0 mmol (1.0 mL); EtOH = 135 mmol; 1
-
5
[d] 1 = 1.5 ∙ 10 mol (0.5 mol%); temperature = 40 °C.
-
6
=
7.5 ∙ 10 mol (0.05 mol%); temperature = 80 °C. First addition: GLY = 13.3
mmol; time = 8 h. Second addition: GLY = 11.9 mmol; time = 16 h.
The formation of MAGEs from GLY was then performed under
optimised reaction conditions using twelve different alcohols
The yield of MAGEs remained constant after two consecutive
additions (at 8 and 16 hours), showing that the catalyst is stable
under the investigated reaction conditions reaching a final
turnover number (TON) higher than 5000.
(
Table1), to enlarge the reaction scope and to obtain MAGEs
with
different
[
chemical-physics
properties
and
then
23,41,42]
applications.
The conversions were determined at two
selected times (1 and 5 hours) in order to evaluate possible
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ChemSusChem
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COMMUNICATION
In order to get deeper insights into the reaction mechanism,
demonstrated that the reaction proceeds well for a large number
of substrates and, in the case of ethanol, with TOF and TON as
1
9
complex 1 was analysed by F NMR in CD
the addition of a large excess of deuterated methanol (See
Supporting Information). Before the addition of CD OD, due to
the paramagnetism of the iron centre any signal was observed in
2 2
Cl , prior and after
-1
high as 1680 h and 5120 respectively, suppressing the
undesirable oligomerization side-reaction. Moreover, all the
3
products have been obtained with
a
high degree of
1
9
the F NMR spectrum. After the addition, a sharp singlet at -76
ppm appeared (-79 in pure CD OD), compatible with the
formation of free triflic acid (HOTf).
regioselectivity (84-96%) toward the non-symmetric regioisomer.
On the basis of the species formed from reaction of the catalyst
and methanol, we proposed a reaction mechanism in which the
Fe-mediated ring-opening of glycidol is the rate limiting step,
justifying the high selectivity and activity of the reaction.
3
[
44]
In concomitance, the
signals of free tetrahydrofuran (THF), at 3.69 and 1.83 ppm, also
1
appeared in the H NMR spectrum. These observations suggest
the formation of an Fe-alcoholate species derived from the
reaction of 1 with methanol. In fact, the formation of this [OSSO]-
2
-
Fe(OMe) derivative was confirmed by HR ESI MS analysis of a
DCM/MeOH solution of 1 (see Supporting Information). The
formation of this species is not unconventional, indeed the
chloride complex 2 has already proven to generate an anionic
Experimental Section
Experimental Details are given in the Supporting Information.
2
-
[
OSSO]-Fe(Br) metallate species in presence of an excess of
[
32]
exogenous halide. According with the observations described
before, we propose the catalytic cycle depicted in Figure 4 for
the regioselective ring-opening of GLY promoted by 1.
Acknowledgements
Ministero dell’Istruzione dell’Università e della Ricerca (MIUR,
Roma, Italy) and Università degli Studi di Salerno (FARB 2017-
ORSA175172), Dr. Patrizia Oliva, Dr. Patrizia Iannece, Dr.
Mariagrazia Napoli, and Dr. Ivano Immediata from Università
degli Studi di Salerno for technical assistance are deeply
acknowledged.
Keywords: iron • glycidol • homogeneous catalysis • glycerol
ethers • ring opening
‡
An update summary of MAGEs synthetic methodologies from direct reaction
of glycidol with alcohols was obtained from the Reaxys® online
database.
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[
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COMMUNICATION
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COMMUNICATION
COMMUNICATION
This study proposes the use of an
Earth-crust abundant metal-based
catalyst for the regioselective
production of monoalkylglyceryl ethers
through ring opening of glycidol with
alcohols under mild reaction
conditions.
F. Della Monica, M. Ricciardi, A. Proto,
R Cucciniello*, C. Capacchione*
Page No. – Page No.
Regioselective Ring Opening of
Glycidol to Monoalkyl Glyceryl Ethers
Promoted by an [OSSO]-Fe(III) Triflate
Complex
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