Efficient and selective hydrocarbon oxidation with sodium periodate catalyzed by supported manganese(III) porphyrin

Article abstract of DOI:10.1007/BF03246055

Manganese(III) tetrakis(p-sulfonatophenyl)porphyrin was successfully bound to silica modified with zirconium. The heterogeneous catalyst, MnTPPS-silica, was characterized by SEM, FT-IR and diffuse reflectance UV-Vis spectroscopic techniques. MnTPPS-silica catalyzes alkene epoxidation and alkanes hydroxylation with sodium periodate under agitation with magnetic stirring and ultrasonic irradiation in the presence of imidazole as an axial ligand. This catalytic system shows a good activity in the epoxidation of linear alkenes. Alkyl aromatic and cycloalkanes were efficiently oxidized to their corresponding alcohols and ketones in the presence of this catalyst. This new heterogeneous catalyst is of high stability and reusability in the oxidation reactions and can be reused several times without loss of its activity.

Full text of DOI:10.1007/BF03246055

J. Iran. Chem. Soc., Vol. 7, No. 3, September 2010, pp. 663-672.
JOURNAL OF THE
Iranian
Chemical Society
Efficient and Selective Hydrocarbon Oxidation with Sodium Periodate Catalyzed by
Supported Manganese(III) Porphyrin
S. Tangestaninejad, M. Moghadam*,V. Mirkhani, I. Mohammadpoor-Baltork and N. Hoseini
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan, 81746-73441, Iran
(Received 17 June 2008, Accepted 18 September 2009)
Manganese(III) tetrakis(p-sulfonatophenyl)porphyrin was successfully bound to silica modified with zirconium. The
heterogeneous catalyst, MnTPPS-silica, was characterized by SEM, FT-IR and diffuse reflectance UV-Vis spectroscopic
techniques. MnTPPS-silica catalyzes alkene epoxidation and alkanes hydroxylation with sodium periodate under agitation with
magnetic stirring and ultrasonic irradiation in the presence of imidazole as an axial ligand. This catalytic system shows a good
activity in the epoxidation of linear alkenes. Alkyl aromatic and cycloalkanes were efficiently oxidized to their corresponding
alcohols and ketones in the presence of this catalyst. This new heterogeneous catalyst is of high stability and reusability in the
oxidation reactions and can be reused several times without loss of its activity.
Keywords: Supported metalloporphyrin, Sodium periodate, Heterogeneous catalyst, Ultrasonic irradiation, Silica gel
INTRODUCTION
prevented progress with practical application for larger scale
oxidation. One way to prepare commercial metalloporphyrin
catalysts is to anchor them onto solid supports. Several
homogeneous and heterogenized metalloporphyrin catalysts
have been developed for oxidation of organic substrates [14-
53].
Silica gel is one of the most frequently used supports in
synthetic organic chemistry because of its inexpensiveness,
ready availability, mechanical robustness, chemical inertness
and facile functionalization. The immobilization of transition
metals on silica gel supports offers a number of advantages
over the traditional solution-phase chemistry. These
heterogeneous catalysts can be recovered from the reaction
media by simple filtration and reused. They do not
contaminate the product solution, and increase the selectivity.
Here, we report the use of Mn(TPPS) supported on silica,
[Mn(TPPS)-silica], in alkene epoxidation and alkane
hydroxylation with sodium periodate in the presence of
imidazole as an axial ligand under mechanical stirring and
Cytochrome P-450 enzymes catalyze various reactions
such as aliphatic and aromatic hydroxylation, olefin
epoxidation and N-, O- and S-oxidation [1,2]. In order to
understand the mechanism of cytochrome P-450
monooxygenation enzyme, synthetic metalloporphyrins were
used as cytochrome P-450 models [3-9]. Amongst them,
manganese porphyrin complexes have been extensively used
in homogeneous catalysis, mainly because of their high
activity and selectivity. Various single oxygen atom donors
-
-
such as PhIO, ClO , H O , ROOH and IO have been used for
2
2
4
oxidation reactions [10-15]. However, these homogeneous
expensive catalysts suffer from three major drawbacks such as
catalyst deactivation by irreversible dimerization, oxidative
self-destruction of metalloporphyrins via an intermolecular
process and non-reusable nature of the catalyst, which have
*
Corresponding author. E-mail: moghadamm@sci.ui.ac.ir

Tangestaninejad et al.
under ultrasonic irradiation conditions.
(20 ml) and filtered. The resin was thoroughly washed with
Et O and combined washings and filtrates were purified on
2
1
EXPERIMENTAL
silica gel plates or silica gel column. IR and H NMR spectral
data confirmed the identities of the products.
All materials were commercial reagent grade. Silica gel 60
was a product of Merck. Alkenes, alkanes and alkylaromatic
compounds were obtained from Merck or Fluka. All of these
compounds were passed through a column containing active
alumina to remove peroxidic impurities. Diffuse reflectance
spectra were recorded on a Shimadzu UV-265 instrument
General Procedure for Oxidation Reactions
Catalyzed by [Mn(TPPS)-Silica] under Ultrasonic
Irradiation
All reactions took place at room temperature in a 40 ml
glass reactor. A UP 400S ultrasonic processor equipped with a
3 mm wide and 140 mm long probe, which was immersed
directly in the reaction mixture, was used for sonication. To a
using optical grade BaSO as reference. Gas chromatography
4
experiments (GC) were performed with a Shimadzu GC-16A
instrument using a 2 m column peaked with silicon DC-200 or
solution of alkene or alkane (1 mmol) in CH CN (10 ml) was
3
1
Carbowax 20 m. H NMR spectra were recorded on a Bruker-
added Mn(TPP)-silica (0.026 mmol). After the addition of
Arance AQS 300 MHz spectrometer. FT-IR spectra were
obtained as potassium bromide pellets in the range 400-4000
cm with a Nicolet-Impact 400D instrument.
The tetraphenylporphyrin ligand was prepared, sulfonated
and metallated according to the methods suggested in
literature [56-58].
sodium periodate solution (2 mmol in 10 ml H O), the mixture
2
was sonicated at room temperature. The progress of the
reaction was followed by GLC. At the end of the reaction, the
silica beads were filtered off and the filtrates were extracted
-
1
with Et O and purified on a silica gel plate or silica gel column
2
(eluent: CCl -Et O). The identities of the products were
4
2
1
confirmed by IR and H NMR spectral data.
Preparation
Porphyrin, [Mn(TPPS)-Silica]
To solution of manganese(III) tetrakis (p-
of
Silica-Supported
Manganese
RESULTS AND DISCUSSION
a
sulfonatophenyl)porphyrin (0.5 g, 0.05 mmol) in methanol (50
ml) was added surface modified silica gel (5 g). The mixture
was vigorously stirred at room temperature for 6 h, the dark
violet resin was collected by filtration, washed thoroughly
with methanol and ethanol respectively, and dried in vacuum
at room temperature. The content of mangenese(III) porphyrin
on the silica support, which was calculated from manganese
content in heterogenized catalyst, was determined by NAA.
Preparation and Characterization of Silica
Supported
[Mn(TPPS)-Silica]
Silica surface modification with 3-aminopropyl
triethoxysilane, POCl and ZrOCl , was carried out through
Manganese
Porphyrin
Catalyst
3
2
the method described by Rodrigues and coworkers [54]. The
supported catalyst was prepared by stirring a suspension of the
support (silica) in a solution of Mn-porphyrin in methanol as
solvent. The catalyst was washed with methanol,
dichloromethane and acetone, consecutively to remove the
free manganese porphyrin. The diffuse reflectance UV-Vis
spectrum of the Mn(TPPS)-silica clearly indicated the
presence of manganese(III) meso-tetrakis(p-sulfonatophenyl)
porphyrin on the surface. The degree of incorporation of
manganese porphyrin on the silica was also determined by
neutron activation analysis (NAA), which showed a value of
about 2.50% w/w. The electrostatic bonding of the silica and
the metalloporphyrin was so strong that Mn-porphyrin could
not be eluted from the silica with water and common organic
General Procedure for Oxidation Reactions
Catalyzed by [Mn(TPPS)-Silica] under Agitation
with Magnetic Stirring
All of the reactions took place at room temperature under
air in a 25-ml flask equipped with a magnetic stirrer bar. A
solution of NaIO (2 mmol) in H O (10 ml) was added to a
4
2
mixture of alkene or alkane (1 mmol) and [Mn(TPPS)-silica]
0.026 mmol) in CH CN (10 ml). The progress of the reaction
(
3
was monitored by GLC. At the end of the reaction, H O (20
2
ml) was added and the reaction mixture was diluted with Et O
2
6
64

Efficient and Selective Hydrocarbon Oxidation with Sodium Periodate
ZrOCl2
O3P
PO3
H P O
PO H
3 2
2
3
Zr
Zr
PO3
PO H
3
2
Zr
Zr
R
_
SO3
MeOH, 4 h
_
N
N
N
_
R:
O3S
Mn
SO3
N
O3P
PO3
Zr
Zr
PO3
Zr
Zr
R
R
R
_
SO3
Scheme 1. Preparation of supported catalyst used in this study
solvents.
The prepared [Mn(TPPS)-silica] catalyst was characterized
by FT-IR, diffuse reflectance UV-Vis, SEM and elemental
analysis.
The reflectance of the silica-bound porphyrin resembled
the solution counterpart spectrum and the Soret band at 467
nm and Q bands at 526, 576 and 608 nm were observed, which
clearly indicated the presence of metalloporphyrins on the
surface (Fig. 1).
In order to ascertain the attachment of porphyrin to the
-
1
silica support, FT-IR spectra were recorded in (4000-400 cm )
regions. The appearance of metalloporphyrin bands in the IR
spectra of the supported catalyst confirmed that Mn(TPPS)
had been supported on the surface of silica (Fig. 2).
Scanning electron micrograph, (SEM), was recorded to
examine the morphological changes occurring on the surface
of the silica. A clear change in the morphology of the silica,
after the introduction of porphirin complex, was observed by
SEM (Fig. 3).
Fig. 1. Diffuse reflectance UV-Vis spectra of [Mn(TPPS)-
Silica].
6
65

Tangestaninejad et al.
Fig. 2. FT-IR spectrum of: (A) silica and (B) [Mn(TPPS)-silica].
6
66

Efficient and Selective Hydrocarbon Oxidation with Sodium Periodate
The Effect of Oxidants on the Oxidation of
Cyclooctene Catalyzed by [Mn(TPPS)-Silica]
In this study, we investigated the effect of different
oxidants such as NaOCl, NaIO , H O , KHSO tert-BuOOH
4
2
2
5
and (n-Bu) NIO on the epoxidation of cyclooctene, catalyzed
4
4
by the heterogeneous Mn(III) porphyrin under agitation with
magnetic stirring (MS) and under ultrasonic irradiation (US).
The results are summarized in Table 1. When, tert-BuOOH
and (n-Bu) NIO4 were used as the oxygen source in
4
acetonitrile, only small amounts of cyclooctene oxide was
detected in the reaction mixture. The use of Oxone (KHSO5)
was not favored because of the disadvantages such the need
for a buffered medium and the bleaching of the metal catalysts
during the oxidation reactions.
The results show that in the presence of the Mn(TPPS)-
silica catalyst, NaIO is the best oxygen source both under
4
mechanical stirring and under ultrasonic irradiation, because
of good oxidation conversion, inertness in the absence of the
catalyst and high solubility in CH CN/H O mixture.
3
2
The Effect of Solvent on the Oxidation of Cyclooctene
Catalyzed by [Mn(TPPS)-Silica]
The epoxidation of cyclooctene was studied in various
solvents under agitation with magnetic stirring (MS) and under
ultrasonic irradiation (US). Among the mixtures of methanol,
ethanol, acetone, acetonitrile (single phase systems),
chloroform, dichloromethane and carbontetrachloride (two
phase systems with Bu NBr as a phase transfer catalyst) with
water, the1:1 mixture of acetonitrile/water was chosen as the
4
Fig. 3. Scanning electron micrograph of: (A) zircunated silica;
B) [Mn(TPPS)-silica].
(
Table 1. The Effect of Oxidants on the Epoxidation of Cyclooctene Catalyzed by [Mn(TPPS)-Silica]a
Epoxide yield (%)
Entry
Oxidant
NaIO
Solvent
MS (8 h)b
US (30 min)b
1
2
3
4
5
6
4
CH
CH
3
3
CN/H
CN/H
2
O
O
97
90
81
33
19
38
96
86
64
48
41
40
Oxone (KHSO
H O
5
)
2
2
2
CH CN
3
NaOCl
CH CN
3
tert-BuOOH
n-Bu NIO
CH CN
3
4
4
CH CN
3
a
Reaction conditions: cyclooctene (1 mmol), oxidant (2 mmol), catalyst (0.026 mmol), CH
10 ml). GLC yield based on starting cyclooctene.
3
CN (10 ml), H O
2
b
(
6
67

Tangestaninejad et al.
reaction medium because of its higher epoxidation yield
Table 2).
styrene, benzaldehyde and acetophenone were produced as by-
(
products. The epoxidation of trans-stilbene under magnetic
stirring led to trans-epoxide in 30% yield, while under
ultrasonic irradiation 71% of trans-epoxide was produced. 1-
Octene and 1-dodecene as linear alkenes were epoxidized
efficiently through this heterogeneous system.
A blank experiment in the presence of oxidant using the
same experimental conditions in the absence the catalyst was
carried out for the epoxidation of cyclooctene. The obtained
Catalytic Alkene Epoxidation with NaIO
by [Mn(TPPS)-Silica]
4
Catalyzed
For the initial studies on the catalytic activity of
Mn(TPPS)-silica], the epoxidation of cyclooctene with NaIO4
[
in the presence of imidazole as an axial ligand was chosen as a
model substrate. The reaction took place at room temperature
under mechanical stirring and under ultrasonisc irradiation in
results showed that NaIO had poor ability to oxidize the
4
1
:1 CH CN/H O mixture. During the course of the
cyclooctene. Moreover, no cyclooctene oxide was detected in
the absence of oxidant in the reaction mixture.
3
2
epoxidation, the reaction solution remained colorless and there
was no evidence of leaching of the catalyst from silica support
into solution. This was further investigated by examining the
UV-Vis spectrum of the filtered reaction mixture and
determining the amount of manganese leached by atomic
absorption spectroscopy. A wide range of substituted alkenes
Oxidation of Alkanes with NaIO4 Catalyzed by
[Mn(TPPS)-Silica]
Direct oxidation of hydrocarbons is one of the typical
reactions of cytochrome P-450 [55]. Therefore, catalytic
oxidation of alkanes with oxygen sources under mild
conditions is an especially justifieable attempt, since direct
functionalization of inactivated C-H bonds in saturated
hydrocarbons usually requires drastic conditions such as high
pressure and high temperature. As shown in Table 4, we have
found that the supported Mn(TPPS) is an efficient catalyst for
the biomimetic functionalization of saturated hydrocarbons. In
the oxidation of the alkanes, the hydroxylation product is
highly dependent on the nature of the hydrocarbon itself.
Cyclooctane, cyclohexane, 1,2,3,4-tetrahydronaphthalene and
adamantane were converted in high yields to their
were oxidized with NaIO in the presence of [Mn(TPPS)-
4
silica] as a catalyst and imidazole as an axial ligand. The
conditions used for epoxidation of other alkenes were identical
to those for cyclooctene. The obtained results show that this
catalyst is an efficient one for alkene epoxidation under
agitation with magnetic stirring and ultrasonic irradiation
(
Table 3). Cyclooctene was oxidized in the presence of the
catalyst in 98% and 99% yields under agitation with magnetic
stirring and under ultrasonic irradiation, respectively. In the
case of cyclohexene, only small amounts of allylic oxidation
was observed. In the oxidation of styrene and &-methyl
a
Table 2. The Effect of Solvent on the Epoxidation of Cyclooctene with NaIO Catalyzed by [Mn(TPPS)-Silica]
4
Entry
Solvent
Epoxide yield (%)
MS (8 h)b
US (30 min)b
1
2
3
4
5
6
7
CH
CH
CH OH/H O
CH CH OH/H O
CHCl /H O
3
3
CN/H
COCH
2
O
98
56
32
20
12
23
9
96
76
45
18
17
16
8
3
/H O
2
3
2
3
2
2
3
2
CH Cl /H O
CCl /H O
2
2
2
4
2
a
Reaction conditions: cyclooctene (1 mmol), oxidant (2 mmol), catalyst (0.026 mmol), CH
ml). GLC yield based on starting cyclooctene.
3
CN (10 ml), H O (10
2
b
6
68

Efficient and Selective Hydrocarbon Oxidation with Sodium Periodate
Table 3. Epoxidation of Alkenes with NaIO Catalyzed by [Mn(TPPS)-Silica] under Agitation with Magnetic Stirring (MS)
4
a
and under Ultrasonic Irradiation (US)
Entry
Alkene
Conversion (%)
Epoxide yield (%)b
Time (min)
MS
98
US
MS
US
99
MS
US
25
1
2
99
81
98
89
480
720
93
78
25
74c
61e
87d
69e
69
59
84
46
960
960
15
15
3
4
5
30
77
30
77
840
25
(
trans-Epoxide)f
(trans-Epoxide)f
6
7
41
38
73
56
40
38
70
43
720
720
25
25
a
O (10 ml). bGLC yield
Reaction conditions: alkene (1 mmol), oxidant (2 mmol), catalyst (0.026 mmol), CH
3
CN (10 ml), H
2
c
d
e
based on starting alkene. 20% Benzaldehyde was produced. 23% Benzaldehyde was produced. The by-product was
acetophenone. Both H NMR and GLC data approved the reported yields.
f
1
corresponding alcohols and ketones. In contrast, ethylbenzene,
propyl benzene and diphenylmethanene only produced the
corresponding ketones. In the case of adamantane, 1-
adamantanol and 2-adamantanone were produced in the
reaction mixture.
washed with the methanol and dried carefully before being
used in the subsequent run. After using the catalyst for four
consecutive times, the epoxide yields were 83% and 79% for
the systems under magnetic stirring and under ultrasonic
irradiation. The amounts of manganese leached were measured
by atomic absorption spectrometry (Table 5).
Catalyst Reuse and Stability
To assess the long-term stability and reusability of
Comparison of Catalytic Activity of Homogeneous
Mn(TPPS) and Heterogeneous [Mn(TPPS)-Silica] in
Alkene Epoxidation and Alkane Hydroxylation with
[Mn(TPPS)-silica], cyclooctene was used as a model substrate,
and recycling experiments were carried out with a single
sample of the catalyst. After each experiment, the catalyst was
separated from the reaction mixture by simple filtration,
Sodium Periodate
In order to demonstrate the effect of supporting on the
6
69

Tangestaninejad et al.
Table 4. Epoxidation of Alkanes with NaIO
4
Catalyzed by [Mn(TPPS)-Silica] under Agitation with Magnetic Stirring
(
MS) and under Ultrasonic Irradiation (US)a
Entry
1
Alkane
Conversion (%)b
Ketone (%)b
Alcohol (%)b
Time (h)
MS
US
71
MS
US
40
MS
32
US
31
MS
US
0.5
5
4
22
8
2
4
6
8
3
62
74
15
37
31
54
30
37
31
40
9
0.5
3
4
11
0.75
3
3
6
9
53
51
36
14
43
30
13
-
-
11
11
11
0.75
0.75
5
25
13
21
6
7
1
3
3
1
44
56
44
31
-
-
0.75
0.75
56
-
11
aCyclooctene (1 mmol), oxidant (2 mmol), catalyst (0.026 mmol), CH
starting alkene.
O (10 ml). GLC yield based on
b
3
CN (10 ml), H
2
Table 5. The Results of [Mn(TPPS)-Silica] Catalyst Recovery and the Manganese Leached in the Epoxidation of
Cyclooctene with Sodium Periodate under Agitation with Magnetic Stirring (MS) and under Ultrasonic
a
Irradiation (US)
Run
Time (h)
Epoxide yield (%)a
Mn leached (%)b
MS
8
8
8
8
US
0.4
0.4
0.4
0.4
MS
98
90
87
83
US
97
90
85
79
MS
US
1.5
1.1
0.7
0
1
2
3
4
1.2
0.9
0.5
0
a
b
GLC yield based on starting alkene. Determined by atomic absorption spectroscopy.
6
70

Efficient and Selective Hydrocarbon Oxidation with Sodium Periodate
Table 6. Comparison of Catalytic Activity of Homogeneous Mn(TPPS) and Heterogeneous [Mn(TPPS)-Silica]
in Alkene Epoxidation and Alkane Hydroxylation with Sodium Periodate
Entry Substrate
Conversion (%)
[Mn(TPPS)-silica]
Time (h)
[Mn(TPPS)-silica]
Mn(TPPS)
21
Mn(TPPS)
8
1
2
98
54
8
8
9
8
Plenum Press, New York, 1995.
catalytic activity of manganese(III) porphyrin in the oxidation
reactions, the epoxidation of cyclooctene and hydroxylation of
cyclooctane with sodium periodate were carried out under the
same reaction conditions and with the same amounts of
[
3]
R.A. Sheldon, in: B. Meunier (Ed.), Biomimetic
Oxidations Catalyzed by Transition Metal Complexes,
Imperial College Press, London, 2000.
B. Meunier, Chem. Rev. 92 (1992) 1411.
D. Mansuy, P. Battioni, J.P. Battioni, Eur. J. Biochem.
[
[
4]
5]
catalyst, substrate, NaIO and imidazole as an axial ligand in a
4
CH CN:H O mixture. The obtained results, which are
3
2
1
84 (1989) 267.
summarized in Table 6, showed that the heterogeneous
Mn(TPPS)-silica] had a higher catalytic activity.
[
[
6]
7]
D. Mansuy, Pure Appl. Chem. 59 (1987) 759.
J.R. Lindsay-Smith, in: R.A. Sheldon (Ed.),
Metalloporphyrins in Catalytic Oxidations, Marcel
Dekker, Chap. 11, New York, 1994, p. 325.
[
CONCLUSIONS
[
[
8]
9]
D. Mansuy, Coord. Chem. Rev. 125 (1993)129.
B.A. Arndtsen, R.G. Bergman, T.A. Mobley, T.H.
Peterson, Acc. Chem. Res. 28 (1995) 154.
We have demonstrated that the silica supported
manganese(III) porphyrin is an efficient catalyst both under
agitation with magnetic stirring and under ultrasonic
irradiation conditions. This catalytic system enjoys the
following advantages: (i) easy preparation and handling of the
tethered catalyst; (ii) increasing catalytic activity in
comparison with the homogeneous counterpart; (iii) increasing
product selectivity and (iv) facile and effective recovery and
recycling of the catalyst.
[
10] M.J. Coon, R.E. White, in: T.G. Spiro (Ed.), Dioxygen
Binding and Activation by Metal Centers, Wiley, New
York, 1980.
[
[
[
[
[
[
[
[
11] J.T. Groves, T.E. Nemo, J. Am. Chem. Soc. 105 (1983)
5
786.
12] O. Bortolini, B. Meunier, J. Chem. Soc. Perkin Trans. 2
1984) 1967.
13] B. Meunier, E. Guilmet, M.E. De Carvalho, R.
Poilblanc, J. Am. Chem. Soc. 106 (1984) 6668.
14] D. Mohajer, S. Tangestaninejad, J. Chem. Soc., Chem.
Commun. (1993) 240.
(
ACKNOWLEDGEMENTS
The support of this work by the University of Isfahan is
gratefully acknowledged.
15] D. Mohajer, S. Tangestaninejad, Tetrahedron Lett. 35
(
1994) 945.
REFERENCES
16] M. Nakamura, T. Tatsumi, H. Tominaga, Bull. Chem.
Soc. Jpn. 63 (1990) 3334.
17] T. Tatsumi, M. Nakamura, H. Tominaga, Chem. Lett.
[
1]
2]
M.C. Feiters, A.E. Rowan, R.J.M. Nolte, Chem. Soc.
Rev. 29 (2000) 375.
(
1989) 419.
[
P.R. Ortiz de Montellano, Cytochrome P-450,
nd
18] W. Nam, H.J. Han, S.Y. Oh, Y.J. Lee, M.H. Choi, S.Y.
Structure, Mechanism and Biochemistry, 2 ed.,
6
71

Tangestaninejad et al.
Han, C. Kim, S.K. Woo, W. Shin, J. Am. Chem. Soc.
22 (2000) 8677.
[40] S. Tangestaninejad, M. Moghadam, J. Chem. Res. (S)
1
(1998) 242.
[
[
19] R. Naik, P. Joshi, S. Umbarkar, R. K. Deshpande, Catal.
Commun. 6 (2005) 125.
20] F.S. Vinhado, P.R. Martins, A.P. Masson, D.G. Abreu,
E.A. Vidoto, O.R. Nascimento, Y. Iamamoto, J. Mol.
Catal. A: Chem. 188 (2002) 141.
[41] S. Tangestaninejad, M. Moghadam, Synth. Commun.
28 (1998) 427.
[42] S. Tangestaninejad, M.H. Habibi, V. Mirkhani, M.
Moghadam, J. Chem. Res. (S) (2001) 444.
[43] M. Moghadam, S. Tangestaninejad, M.H. Habibi, V.
Mirkhani, J. Mol. Cat. A: Chemical 217 (2004) 9.
[44] S. Tangestaninejad, M. Moghadam, V. Mirkhani, H.
Kargar, Ultrason. Sonochem. 10 (2006) 32.
[45] M. Moghadam, S. Tangestaninejad, V. Mirkhani, I.
Mohammadpoor-Baltork, H. Kragar, Bioorg. Med.
Chem. 13 (2005) 2901.
[46] M. Moghadam, M. Nasr-Esfahani, S. Tangestaninejad,
V. Mirkhani, M.A. Zolfigol, Can. J. Chem. 84 (2006) 1.
[47] M. Moghadam, S. Tangestaninejad, V. Mirkhani, H.
Kargar, H. Komeili-Isfahani, Catal. Commun. 6 (2005)
688.
[48] S. Tangestaninejad, M.H. Habibi, V. Mirkhani, M.
Moghadam, Molecules 7 (2002) 264.
[49] S. Tangestaninejad, V. Mirkhani, Chem. Lett. 12 (1998)
1265.
[50] V. Mirkhani, S. Tangestaninejad, M. Moghadam, B.
Yadollahi, J. Chem. Res. (S) (2000) 515.
[51] M. Nasr-Esfahani, M. Moghadam, S. Tangestaninejad,
V. Mirkhani, Bioorg. Med. Chem. Lett. 15 (2005) 3276.
[52] M. Moghadam, V. Mirkhani, S. Tangestaninejad, I.
Mohammadpoor-Baltork, A.A. Abbasi-Larki, Appl.
Catal. A: Gen. 349 (2008) 177.
[53] M. Moghadam, V. Mirkhani, S. Tangestaninejad, I.
Mohammadpoor-Baltork, H. Kargar, J. Mol. Catal. 288
(2008) 116.
[
[
[
[
[
[
[
[
[
[
[
[
[
[
[
[
21] R. Paul, R. Cooke, R.J. Lindsay Smith, J. Chem. Soc.,
Perkin Trans. 1 (1994) 1913.
22] H. C. Sacco, Y. Iamamoto, J. R. Lindsay Smith, J.
Chem. Soc., Perkin Trans. 2 (2001) 181.
23] F.S. Vinhado, C.M.C. Prado-Manso, H.C. Sacco, Y.
Iamamoto, J. Mol. Catal. A: Chem. 174 (2001) 279.
24] Z. Li, C.-G. Xia, X.-M. Zhang, J. Mol. Catal. A: Chem.
1
85 (2002) 47.
25] J. Poltowicz, E.M. Serwicka, E. Bastardo-Gonzalez, W.
Jones, R. Mokaya, Appl. Catal. A 218 (2001) 211.
26] M.A. Schiavon, Y. Iamamoto, O.R. Nascimento, M.D.
Assis, J. Mol. Catal. A: Chem. 174 (2001) 213.
27] M.D. Assis, J.R. Lindsay Smith, J. Chem. Soc., Perkin
Trans. 2 (1998) 2221.
28] F.G. Doro, J.R. Lindsay Smith, A.G. Ferreira, M.D.
Assis, J. Mol. Catal. A: Chem. 164 (2000) 97.
29] P. Battioni, O. Brigaud, H. Desvaux, D. Mansuy, T.G.
Traylor, Tetrahedron Lett. 32 (1991) 2893.
30] T.G. Traylor, Y.S. Byun, P.S. Traylor, P. Battioni, D.
Mansuy, J. Am. Chem. Soc. 113 (1991) 7821.
31] P. Battioni, J.F. Bartoli, D. Mansuy, Y.S. Byun, T.G.
Traylor, J. Chem. Soc., Chem. Commun. (1991) 1051.
32] M. Benaglia, T. Danelli, G. Pozzi, Org. Biomol. Chem.
1
(2003) 454.
33] E. Brule, K.K. Hii, Y.R. de Miguel, Org. Biomol.
Chem. 3 (2005) 1971.
34] J.-L. Zhang, Y.L. Liu, C.-M. Che, Chem. Commun.
[54] M.A. Rodrigues, M.P. Bemquere, M.J. Politi, S.
Brochsztain, M.T. Miranda, S.B. Mauricio, Chem. Lett.
25 (2002) 604.
(2002) 2906.
35] R. Zhang, W.-Y. Yu, H.-Z. Sun, W.-S. Liu, C.-M. Che,
Chem. Eur. J. 8 (2002) 2495.
36] X.-Q. YU, J.-S. Huang, W.-Y. Yu, C.-M. Che, J. Am.
Chem. Soc. 122 (2000) 5337.
[55] P.R. Ortiz de Montellano, Cytochrome P-450,
nd
Structure, Mechanism and Biochemistry, 2
Plenum Press, New York, 1995.
ed.,
[56] A.D. Alder, F.R. Long, F. Kampass, J. Kim. J. Inorg.
Nucl. Chem. 32 (1970) 2443.
[57] C.A. Busby, R.K. DiNello, D. Dolphin, Can. J. Chem.
53 (1975) 1554.
[
[
37] J.-L. Zhang, C.-M. Che, Org. Lett. 4 (2002) 1911.
38] C.-J. Liu, W.-Y. Yu, S.-G. Li, C.-M. Che, J. Org.
Chem. 63 (1998) 7364.
[
39] S. Tangestaninejad, V. Mirkhani, J. Chem. Res. (S)
[58] A. Harriman, G. Porter, J. Chem. Soc., Faraday 2, 75
(1979) 1532.
(
1998) 788.
6
72