Polystyrene-bound electron-deficient tin(IV) porphyrin: A new, highly efficient, robust and reusable catalyst for acetylation of alcohols and phenols with acetic anhydride

Article abstract of DOI:10.1016/j.crci.2011.06.001

In the present work, tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [Sn^IV(TNH₂PP)(OTf) ₂], supported on chloromethylated polystyrene was prepared and characterized by elemental analysis, FT IR and diffuse reflectance UV-Vis spectroscopic methods. This new heterogenized catalyst was used for acetylation of alcohols and phenols with acetic anhydride in short reaction times and high yields. The catalyst is of high reusability and stability in the acetylation reactions and was recovered several times without loss of its initial activity and catalyst leaching.

Full text of DOI:10.1016/j.crci.2011.06.001

C. R. Chimie 14 (2011) 1080–1087
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Full paper/Memoire
Polystyrene-bound electron-deficient tin(IV) porphyrin: A new, highly
efficient, robust and reusable catalyst for acetylation of alcohols and
phenols with acetic anhydride
*
*
Majid Moghadam , Shahram Tangestaninejad , Valiollah Mirkhani,
Iraj Mohammadpoor-Baltork, Shadab Gharaati
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran
A R T I C L E I N F O
A B S T R A C T
Article history:
In the present work, tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfo-
nate, [SnIV(TNH2PP)(OTf)2], supported on chloromethylated polystyrene was prepared and
characterized by elemental analysis, FT IR and diffuse reflectance UV-Vis spectroscopic
methods. This new heterogenized catalyst was used for acetylation of alcohols and
phenols with acetic anhydride in short reaction times and high yields. The catalyst is of
high reusability and stability in the acetylation reactions and was recovered several times
without loss of its initial activity and catalyst leaching.
Received 8 May 2011
Accepted after revision 1 June 2011
Available online 22 July 2011
Keywords:
Alcohol
Phenol
´
ß 2011 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
Acetylation
Polystyrene
High-valent tin(IV) porphyrin
1. Introduction
The protection of hydroxyl groups is often necessary
during the course of various transformations in a synthetic
The development of environmentally benign synthesis
has attracted much attention in recent years. Therefore,
development of polymer-bound catalysts and reagents
with high activity and selectivity is of great importance in
organic synthesis [1–3]. Since most of metal complexes are
often expensive to purchase or prepare, the immobiliza-
tion of these complexes on a support can provide catalysts
which are easier to handle, and may exhibit improved
selectivities and activities because of the support environ-
ment [4].
From synthetic point of view, polystyrene is one of the
most popular polymeric supports used in synthetic organic
chemistry because of its low cost, ready availability,
mechanical robustness, chemical inertness, and facile
functionalization.
sequence, especially in the synthesis of fine chemicals and
natural products. Several methods such as acetylation,
tetrahydropyranylation, methoxymethylation and tri-
methylacetylation have been reported for protection of
hydroxyl groups [5,6]. A variety of procedures using
homogeneous or heterogeneous catalysts such as iodine
[7], p-toluenesulfonic acid [8], alumina [9], zinc chloride
[10], cobalt chloride [11], montmorillonite K-10 and KSF
[12], zeolite HSZ-360 [13], zirconium sulfophenyl phos-
phonate [14], Sc(OTf)3 [15], TaCl5 [16], TMSOTf [17],
Cu(OTf)2 [18], In(OTf)3 [19], magnesium bromide [20],
bismuth(III) salts [21], ferric perchlorate adsorbed on
silica-gel [22], RuCl3 [23], InCl3 [24], Ce(OTf)3 [25],
Mg(ClO4)2 [26], ZrCl4 [27], Cp2ZrCl2 [28], ZrOCl2Á8H2O
[29], Al(OTf)3 [30], NaHSO4ÁSiO2 [31], La(NO3)3Á6H2O [32],
NbCl5 [33], Gd(OTf)3 [34], Alumina supported MoO3 [35],
cerium polyoxometalate [36], Zn(ClO4)2Á6H2O [37],
Mg(NTf2)2 [38], Cu(BF4)2 [39], BiO(ClO4)2 [40], HClO4-
SiO2 [41], HBF4-SiO2 [42], electron-deficient tin [IV]
porphyrins [43–45] and ZrO(OTf)2 [46] have been routine-
* Corresponding authors.
E-mail addresses: moghadamm@sci.ui.ac.ir (M. Moghadam),
stanges@sci.ui.ac.ir (S. Tangestaninejad).
1631-0748/$ – see front matter ß 2011 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
doi:10.1016/j.crci.2011.06.001

M. Moghadam et al. / C. R. Chimie 14 (2011) 1080–1087
1081
ly reported for acetylation of alcohols and phenols with
Ac2O. Although these procedures provide an improvement,
many of these catalysts or activators need long reaction
times, drastic reaction conditions or tedious work-up and
are moisture-sensitive or expensive in terms of the
catalyst. Hence, the introduction of new procedures to
circumvent these problems is still in demand.
Electron-deficient metalloporphyrins have been used as
mild Lewis acid catalysts [47–50]. The Suda group has
reported the use of chromium and iron porphyrins in
organic synthesis. They used Cr(tpp)Cl for regioselective
[3,3] rearrangement of aliphatic allyl vinyl ethers and for
Claisen rearrangement of simple aliphatic allyl vinyl ethers,
for 72 h. After cooling to room temperature, the green solids
were filtered, washed with Et2O and acetone and dried.
2.2. Conversion of [SnIV(TNH2PP)Cl2]@CMP to
[SnIV(TNH2PP)(OTf)2]@CMP
To a suspension of [SnIV(TNH2PP)Cl2]@CMP (2 g) in THF
(50 mL) was added NaOTf (1 g) and stirred at 60 8C for 8 h,
after which the catalyst was filtered and washed with THF.
2.3. General procedure for acetylation of alcohol and phenols
with Ac2O catalyzed by [SnIV(TNH2PP)(OTf)2]@CMP
To a solution of alcohol or phenol (1 mmol) and Ac2O
(3 mmol per OH group) in CH3CN (0.5 mL) was added
[SnIV(TNH2PP)Cl2]@CMP (70 mg, 0.01 mmol) and stirred at
room temperature for appropriate time. The progress of the
reaction was monitored by GC. After completion of the
reaction, Et2O (10 mL) was added and the catalyst was
filtered. The filtrates were washed with brine, dried over
Na2SO4 and concentrated under reduced pressure to afford
the crude product.
Fe(tpp)OTf for rearrangement of
a,b-epoxy ketones into
1,2-diketones and Cr(tpp)OTf for highly regio- and stereo-
selective rearrangement of epoxides to aldehydes [51–54].
Recently, we have reported the use of tetraphenylpor-
phyrinatotin(IV) perchlorate [43,55], tetraphenylporphyri-
natotin(IV) trifluoromethanesulfonate [44,56–59], and
tetraphenylporphyrinato- tin(IV) tetrafluoroborate [45,59–
61] in organic transformations.
In the present work, we report the preparation,
characterization and investigation of catalytic activity of
tetrakis(p-aminophenyl)porphyrinatotin(IV)
2.4. Catalyst reusability
trifluoro-
methanesulfonate, [SnIV(TNH2PP)(OTf)2], supported on
chloromethylated polystyrene in the acetylation of alco-
hols and phenols with acetic anhydride (Scheme 1).
At the end of each reaction, the catalyst was filtered,
washed thoroughly with Et2O, dried and reused.
3. Results and discussion
2. Experimental
3.1. Preparation and characterization of
[SnIV(TNH2PP)(OTf)2]@CMP
Chemicals werepurchasedfromMerckorFlukachemical
companies. Chloromethylated polystyrene (cross-linked
with 2% divinylbenzene, 4–5% Cl content, 1.14–
1.40 mmol/g Cl) was purchased from Fluka. FT IR spectra
were obtained with potassium bromide pellets in the range
400–4000 cmÀ1 with a Nicolet Impact 400D spectrometer.
Gas chromatography experiments (GC) were performed
with a Shimadzu GC-16A instrument using a 2-m column
packed with silicon DC-200 or Carbowax 20 m. In the GC
experiments, n-decane was used as an internal standard. 1H
NMR spectra were recorded on a Bruker-Avance AQS
400 MHz spectrometer. Tetra(4-aminophenyl)porphyrin
was prepared according to the literature [62]. The
[SnIV(TNH2PP)Cl2] catalyst was prepared according to the
procedure reported for metallation of porphyrins [63]. In
this manner, tetra(4-aminophenyl)porphyrin was reacted
with SnCl2Á2H2O in refluxing DMF.
Scheme 2 shows the preparation route for [SnIV(TNH2P-
P)(OTf)2]@CMP. First, chloromethylated polystyrene
(cross-linked with 2% divinylbenzene, 4–5% Cl content,
1.14–1.40 mmol/g Cl) was reacted with [SnIV(TNH2PP)Cl2]
to afford the [SnIV(TNH2PP)Cl2]@CMP. Then, the chlorines
were substituted by OTfÀ by the reaction of
[SnIV(TNH2PP)Cl2]@CMP with NaOTf. This substitution
increases the electron-deficiency of tin(IV).
The prepared catalyst was characterized by elemental
analysis, FT IR and UV-Vis spectroscopic methods. The
nitrogencontentofthecatalyst, measuredbyCHNSanalysis,
was obtained as 1.64% (1.17 mmol/g). According to this
value, the amount of porphyrin introduced to polystyrene
was calculated as 0.146 mmol/g. The Sn content of the
catalyst was also determined by ICP (0.143 mmol/g) which
was in accordance with the data obtained by CHNS analysis.
The evidence for attachment of tin(IV) porphyrin on the
polystyrene was obtained from FT IR spectra of chloro-
methylated polystyrene and [SnIV(TNH2PP)(OTf)2]@CMP.
The sharp C-Cl peak (due to -CH2Cl groups) at 1264 cmÀ1 in
the starting polymer (Fig. 1A) was practically absent or seen
as a weak band after introducing of tin(IV) porphyrin on the
polymer (Fig. 1B). A peak at 1622 cmÀ1 assigned to C = N and
a peak at 1175 cmÀ1 assigned to C-N stretching modes also
appeared, which confirmed the supporting of tin(IV)
porphyrin on the support.
2.1. Supporting of [SnIV(TNH2PP)Cl2] on chloromethylated
polystyrene, [SnIV(TNH2PP)Cl2]@CMP
Toa solution of [SnIV(TNH2PP)Cl2] (0.5 g)in DMF (50 mL),
were added chloromethylated polystyrene (2.5 g) and
triethylamine (3 mL). The mixture was heated at 100 8C
[SnIV(TNH2PP)(OTf)2]@CMP
Ac2O, CH3CN
R
OH
or
R
OAc
or
Ar OH
Ar OAc
The reflectance spectrum of the polymer-bound por-
phyrin resembles solution counterpart spectrum with only
Scheme 1. Acetylation of alcohols and phenols with Ac2O catalyzed by
[SnIV(TNH2PP)(OTf)2]@CMP.

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M. Moghadam et al. / C. R. Chimie 14 (2011) 1080–1087
NH2
Cl
N
N
N
N
Sn
Cl
NH2
CH2Cl
H2N
+
NH2
NH2
DMF, 100 o
Et3N, 72 h
C
Cl
N
N
N
Sn
Cl
NH2
H2CHN
N
THF, 60 oC
NaOTf, 8 h
NH2
NH2
OTf
N
N
N
Sn
NH2
H2CHN
N
OTf
NH2
Scheme 2. The preparation route for [SnIV(TNH2PP)(OTf)2]@CMP.
a slight red shift, and the Soret band was appeared at
445 nm and the Q bands observed at 558 and 619 nm.
These observations clearly proved the presence of metal-
loporphyrin on the polystyrene (Fig. 2).
the acetylation of 4-chlorobenzyl alcohol with Ac2O. In this
case, only 23% of the corresponding acetate was obtained
while in the presence of [SnIV(TNH2PP)(OTf)2]@CMP, the
reaction was completed after 6 min. These observations
indicated that the presence of OTf groups is necessary for
catalytic activity of tin(IV) porphyrin. The OTf groups
increases the electron-deficiency of tin(IV) porphyrin
which in turn increases the activity of the catalyst.
3.2. Acetylation of alcohols and phenols with Ac2O catalyzed
by [SnIV(TNH2PP)(OTf)2]@CMP
First, the amount of catalyst was optimized in the
acetylation of 4-chlorobenzyl alcohol with Ac2O. The
results, which are summarized in Table 1, showed that
in the presence of 0.01 mmol (70 mg) of [SnIV(TNH2
PP)(OTf)2]@CMP the highest yield was obtained. Then,
the amount of Ac2O was also optimized. The results
showed that in the presence of 3 mmol of Ac2O, the
reaction was completed (Table 2).
The optimized conditions, which were obtained for
acetylation of 4-chlorobenzyl alcohol, were alcohol, Ac2O
and catalyst in a molar ratio of 100: 300: 1. Under these
conditions, a wide variety of alcohols were subjected to
acetylation with Ac2O. The obtained results showed that
different primary, secondary (including aliphatic and
aromatic alcohols) and tertiary alcohols were acetylated
successfully at room temperature (Table 3). As can be seen,
in benzylic alcohols the nature of substituent (electron-
withdrawing or electron-releasing) has no significant
effect on the product yield. In the absence of catalyst only
In order to show the effect of OTf groups on the catalytic
activity of tin (IV) porphyrin, the catalytic activity of
[SnIV(TNH2PP)Cl2]@CMP (1 mol%) was also investigated in

M. Moghadam et al. / C. R. Chimie 14 (2011) 1080–1087
1083
Fig. 2. The DR UV-Vis spectrum of [SnIV(TNH2PP)(OTf)2]@CMP.
Table 2
Optimization of Ac2O amount in the acetylation of 4-chlorobenzyl
alcohola.
Entry
Time (min)
Ac2O (mmol)
Yield (%)b
1
2
3
4
5
6
6
6
6
6
6
6
0.5
1.0
1.5
2.0
2.5
3.0
18
38
55
81
92
100
Fig. 1. The FT IR spectrum of (A) chloromethylated polystyrene and (B)
[SnIV(TNH2PP)(OTf)2]@CMP.
a
Reaction conditions: alcohol (1 mmol), Ac2O, catalyst (1 mol%),
CH3CN (1 mL).
b
GC yield.
small amounts of the corresponding acetates were
produced. In the case of tertiary alcohols such as 1-
adamantol and 2-methyl-1-phenyl-2-propanol (entries 17
and 18) no elimination product was observed.
In order to show the advantage of the presented method
in the acetylation reactions, we have compared the
obtained results in the acetylation of benzyl alcohol with
acetic anhydride catalyzed by [SnIV(TNH2PP)(OTf)2]@CMP
with some of those reported in the literature (Table 4). It is
clear that the method presented is superior in terms of
reaction time, catalyst amount, or product yield. Recently,
we reported the use of homogeneous [SnIV(TPP)(OTf)2] and
[SnIV(TPP)(BF4)2] in the acetylation of alcohols and phenols
[44,45]. The reaction times in the presence of 1 mol% of
homogeneous catalysts were 1–15 min and the product
yields were 87–99%. In comparison with its homogeneous
counterparts [44,45], in the presence of
1 mol% of
[SnIV(TNH2PP)(OTf)2]@CMP, the corresponding acetates
were obtained in 96–100% in 8–12 min. These observations
showed that [SnIV(TNH2PP)(OTf)2]@CMP, which is
a
heterogeneous catalyst, in some cases the reaction times
are longer for [SnIV(TNH2PP)(OTf)2]@CMP. On the other
hand, the reusability of this catalyst was higher and can be
separated by simple filtration in which does not contami-
nate the reaction product.
Table 1
Optimization of catalyst amount in the acetylation of 4-chlorobenzyl
alcohol with Ac2Oa.
Under the optimized conditions, which were described
for acetylation of alcohols, the acetylation of phenols with
Ac2O was also investigated in the presence of [SnIV(TNH2P-
P)(OTf)2]@CMP. The results showed that all reactions were
completed after 8 min at room temperature (Table 5). The
acetylation of polyhydroxybenzenes such as hydroqui-
none, pyrocatechol, resorcinol and pyrogallol was also
performed. The results showed that all hydroxyl groups
were acetylated and the desired polyacetates were
obtained in excellent yields (Table 5, entries 5–8).
Entry
Time (min)
Catalyst amounts
(mmol, mg)
Yield (%)b
1
2
3
4
5
6
6
6
6
6
40 mg (0.006 mmol)
50 mg (0.0071 mmol)
60 mg (0.0086 mmol)
70 mg (0.010 mmol)
80 mg (0.011 mmol)
31
54
88
100
100
a
Reaction conditions: alcohol (1 mmol), Ac2O (3 mmol), catalyst,
CH3CN (1 mL).
b
GC yield.

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M. Moghadam et al. / C. R. Chimie 14 (2011) 1080–1087
Table 3
Acetylation of alcohols with Ac2O catalyzed by [SnIV(TNH2PP)(OTf)2]@CMP at room temperaturea.
Entry
1
Hydroxy compound
Acetate
Time (min)
6
Yield (%)b,c
100 (95)
CH2OH
CH2OAc
CH2OAc
CH2OAc
CH2OAc
NO2
2
3
4
6
100 (96)
100 (95)
100 (93)
Cl
CH2OH
CH2OH
Cl
6
O2N
O2N
12
CH2OH
NO2
5
6
6
6
100
100
MeO
Me
CH2OAc
MeO
Me
CH2OH
CH2OAc
OMe
CH2OH
OMe
7
6
6
100 (96)
100
CH2OH
CH2OH
CH2OAc
CH2OAc
8
9
Me
Me
6
6
100 (94)
CH2OH
CH2OAc
Me
Me
10
100
CH2CH2CH2OAc
CH2CH2CH2OH
OH
OH
OAc
OAc
11
12
13
6
6
6
100
100
100
OH
OAc
OAc
Me
Me
14
15
6
6
100 (95)
100 (93)
OH
OH
OAc
16
17
OH
OAc
6
8
99
96
OH
OAc
Me
OAc
Me
OH
Me
18
8
98 (90)
Me
a
Reaction conditions: alcohol (1 mmol), Ac2O (3 mmol), catalyst (1 mol%), CH3CN (1 mL).
b
c
GC yield.
Yields in the parentheses refer to isolated products.

M. Moghadam et al. / C. R. Chimie 14 (2011) 1080–1087
1085
Table 4
Comparison of the results obtained for the acetylation of benzyl alcohol catalyzed by [SnIV(TNH2PP)(OTf)2]@CMP with those obtained by the recently
reported catalysts.
catalyst
CH2OH
CH2OAc
Entry
Catalyst
Catalyst (mol%)
Temperature
Time (min)
Yield (%)
Ref.
1
2
[SnIV(TNH2PP)(OTf)2]@CMP
I2
1
RT
RT
RT
RT
60 8C
RT
RT
RT
RT
RT
RT
RT
RT
RT
RT
RT
RT
RT
6
1
100
99
98
90
84
77
97
97
98
96
99
95
85
98
100
93
99
99
-
10
[7]
3
CoCl2
0.5
240
60
60
-
[11]
[12]
[13]
[16]
[18]
[19]
[21]
[21]
[21]
[23]
[24]
[25]
[26]
[28]
[44]
[45]
4
Montmorillonite KSF
Zeolite HSZ-360
TaCl5
20 mg
5
20 mg
6
10 mg
7
Cu(OTf)2
2
30
15
35
60
5
8
In(OTf)3
0.1
10
5
9
BiCl3
10
11
12
13
14
15
16
17
18
Bi(TFA)3
Bi(OTf)3
1
RuCl3
5
10
30
12
15
600
1
InCl3
0.1
1
Ce(OTf)3
Mg(ClO4)2
Cp2ZrCl2
[SnIV(TPP)(OTf)2]
[SnIV(TPP)(BF4)2]
1
1
1
1
1
Table 5
Acetylation of phenols with Ac2O catalyzed by [SnIV(TNH2PP)(OTf)2]@CMP at room temperaturea.
Entry
1
Phenol
Acetate
Time (min)
Yield (%)b,c
100 (96)
8
8
8
8
OAc
OH
2
3
4
100 (95)
100 (93)
100 (95)
Cl
OAc
OAc
Cl
OH
OH
OH
OH
O2N
O2N
H3C
AcO
OAc
OAc
H3C
HO
5d
6d
8
8
100 (94)
100
OAc
OAc
OH
OH
7d
8
100
OH
OAc
HO
HO
AcO
AcO
8d
8
8
100
OH
OAc
OH
OH
OAc
OAc
9
100 (94)
a
Reaction conditions: phenol (1 mmol), Ac2O (3 mmol), catalyst (1 mol%), CH3CN (1 mL).
GC yield.
b
c
Yields in the parentheses refer to isolated products.
Reaction was performed with 2 mmol of Ac2O per OH group.
d

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M. Moghadam et al. / C. R. Chimie 14 (2011) 1080–1087
O
O
O
and Ac2O. The catalyst was consecutively reused seven
H3C
H3C
times without a detectable catalyst leaching or a signifi-
cant loss of its activity. After each run the filtrates were
used for determination of catalyst leaching. No Sn was
detected in the filtrates by ICP. This is not surprising
because the reaction times are short. When the same
reaction was continued for 2 h, about 2% of initial Sn was
leached. Also, the catalytic behavior of the separated liquid
was tested by addition of fresh 4-chlorobenzyl alcohol and
Ac2O to the filtrates after each run. Execution of the
acetylation reaction under the same reaction conditions, as
with catalyst, showed that the obtained results were as
same as blank experiments. The nature of recovered
catalyst was monitored by diffuse reflectance UV-Vis
spectrophotometery. No change was observed in the DR
UV-Vis spectrum of the catalyst which indicates the
stability and robustness of the catalyst (Fig. 3).
H3C
H3C
O
O
IV
Sn
O
IV
Sn
1
O
C
O
C
H3C
OH
+ RO
CH3
ROH
Scheme 3. The proposed mechanism.
4. Conclusion
In conclusion, a new, robust, stable and heterogeneous
tin(IV) catalyst was prepared, characterized for the first
time. This new electron-deficient tin(IV) porphyrin,
[SnIV(TNH2PP)(OTf)2]@CMP, was used for efficient and
chemoselective acetylation of primary, secondary and
tertiary alcohols and phenols with Ac2O. Short reaction
times, excellent yields, easy work-up and reusability and
stability of the catalyst are noteworthy advantages of this
method.
The actual mechanism is not clear at present. However,
a plausible explanation is that acetic anhydride is first
activated by catalyst to afford 1. Alcohol or phenol attacks
1 which in turn converts to the final product and releases
the catalyst for the next catalytic cycle (Scheme 3).
3.3. Catalyst reuse and stability
The stability of the [SnIV(TNH2PP)(OTf)2]@CMP catalyst
was monitored using multiple sequential acetylation of
4-chlorobenzyl alcohol with Ac2O. For each of the repeated
reactions, the catalyst was filtered, washed exhaustively
with water, acetonitrile and diethyl ether, respectively,
and dried before using with fresh 4-chlorobenzyl alcohol
Acknowledgement
We are thankful to the Center of Excellence of
Chemistry of University of Isfahan (CECUI) for financial
support of this work.
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