A diphosphino-functionalised MCM-41-anchored platinum complex: An efficient and reusable catalyst for the hydrosilylation of olefins

Article abstract of DOI:10.3184/030823410X12887259824283

A diphosphino-functionalised MCM-41 anchored platinum complex (MCM-41-2P-Pt) was conveniently synthesised from commercially available and cheap γ-aminopropyltriethoxysilane via immobilisation on MCM-41, followed by reactiopn with diphenylphosphinomethanol and potassium chloroplatinite. It was found that the title complex is a highly efficient catalyst for the hydrosilylation of olefins with triethoxysilane and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 10 consecutive reactionss without any decrease in activity.

Full text of DOI:10.3184/030823410X12887259824283

648 RESEARCH PAPER
NOVEMBER, 648–652
JOURNAL OF CHEMICAL RESEARCH 2010
A diphosphino-functionalised MCM-41-anchored platinum complex: an
efficient and reusable catalyst for the hydrosilylation of olefins
Lingfang Zha, Wenyan Hao and Mingzhong Cai*
Department of Chemistry, Jiangxi Normal University, Nanchang 330022, P. R. China
A diphosphino-functionalised MCM-41 anchored platinum complex (MCM-41-2P-Pt) was conveniently synthesised
from commercially available and cheap γ-aminopropyltriethoxysilane via immobilisation on MCM-41, followed by
reactiopn with diphenylphosphinomethanol and potassium chloroplatinite. It was found that the title complex is a
highly efficient catalyst for the hydrosilylation of olefins with triethoxysilane and can be recovered and recycled by
a simple filtration of the reaction solution and used for at least 10 consecutive reactionss without any decrease in
activity.
Keywords: supported catalyst, diphosphino-functionalised MCM-41, platinum complex, hydrosilylation, heterogeneous
catalysis
The hydrosilylation of alkenes is one of the most important
Si–C bond formation reactions in organosilicon chemistry and
a variety of silicon monomers containing functional groups
have been synthesised by this reaction.1 Many metal complexes
are known to be catalysts for the reaction,2,3 but the discovery
by Speier et al.,4 Louis et al.5 and Maciejewski et al.6 that
hexachloroplatinic acid is a highly efficient catalyst, even
under ambient conditions, has led to Pt complexes becoming
the catalysts of choice for these reactions. Generally, hydrosi-
lylation is performed in the liquid phase using a homogeneous
catalyst. However, separation of the catalyst from the reaction
mixture is troublesome. From the standpoint of green chemis-
try, the development of more environmentally benign condi-
tions for the reaction, for example, the use of a heterogeneous
platinum catalyst would be desirable. Polymer-supported tran-
sition metal complex catalysts are used more and more widely
because they can combine the advantages of easy catalyst
recovery, characteristic for a heterogeneous catalyst, with the
high activity and selectivity of soluble complexes.7–9 In the
preparation of supported catalysts a wide variety of support
materials have been used including cross-linked polymers,10–12
silica,13–18 glass fibre19 and dendrimers.20–23 The support mate-
rial and surface modifier frequently plays a crucial role in the
performance of the resulting supported catalyst. Basically, the
support has to be thermally and chemically stable during
the reaction process and has to provide accessibility and a
good dispersion of the active sites.
Study of new types of supported platinum complexes cata-
lysts which might be suitable for hydrosilylation of olefins
with triethoxysilane has theoretical and practical significance.
Development of the mesoporous material MCM-41 provided a
new possible candidate for a solid support for immobilisation
of homogeneous catalysts.24 MCM-41 has a regular pore
diameter of ca.5 nm and a specific surface area > 700 m2 g−1.25
Its large pore size allows passage of large molecules such as
organic reactants and metal complexes through the pores to
reach the surface of the channel.26–28 Shyu et al. reported the
immobilisation of Rh(PPh3)3Cl on phosphinated MCM-41 for
catalytic hydrogenation of olefins and found that the turnover
frequency (TOF) of this MCM-41-supported phosphine
rhodium complex is three times higher than that of Rh(PPh3)3Cl
in the hydrogenation of cyclohexene.29 However, to the best of
our knowledge, no hydrosilylation reactions of olefins with
triethoxysilane catalysed by a MCM-41-supported phosphine
platinum complex have been reported until now. It is generally
believed that high surface area of a heterogeneous catalyst
results in high catalytic activity. Considering the fact that
MCM-41 support has an extremely high surface area and the
catalytic platinum species is anchored on the inner surface of
the mesopore of the MCM-41 support, we expect that an
MCM-41-supported phosphine platinum catalyst will exhibit
high activity and good reusability. In this paper, we wish
to report the synthesis of the diphosphino-functionalised
MCM-41-anchored platinum complex (MCM-41-2P-Pt) and
its catalytic properties in the hydrosilylation of olefins with
triethoxysilane.
Over the past decade the N,N-bis(diphenylphosphinomethyl)
amino-functionality has been used for the preparation of
dendrimer-supported and supramolecular homogeneous cata-
lysts.30–32 Alper and coworkers first reported the synthesis of a
polymeric ligand containing the N,N-bis(diphenylphosphinom
ethyl)amino-functionality by using the Mannich reaction.33
Just recently insoluble versions of this chelating phosphine
ligand have been applied in Rh-catalysed hydroformylation,34
Rh-catalysed hydrogenation,35 Pd-catalysed Stille coupling,36
and Pd-catalysed carbonylative cross-coupling of aryl iodides
with organoboron or organotin compounds.37,38 The novel
diphosphino-functionalised MCM-41-anchored platinum
complex (MCM-41-2P-Pt) was conveniently synthesised from
commercially available and cheap γ-aminopropyl-triethoxysi-
lane via immobilisation on MCM-41, followed by reaction
with diphenylphosphinomethanol, which resulted from adduct
formation between diphenylphosphine and paraformaldehyde,
and potassium chloroplatinite (Scheme 1).
X-ray powder diffraction (XRD) patterns of the parent
MCM-41 and the modified materials MCM-41-2P, MCM-41-
2P-Pt are displayed in Fig. 1. Small angle X-ray powder dif-
fraction of the parent MCM-41 gave peaks corresponding to
hexagonally ordered mesoporous phases. For MCM-41-2P
and MCM-41-2P-Pt, the (100) reflection of the parent MCM-
41 with decreased intensity remained after functionalisation,
while the (110) and (200) reflections became weak and dif-
fuse, which could be due to contrast matching between the
silicate framework and organic moieties which are located
inside the channels of MCM-41. These results indicated that
the basic structure of the parent MCM-41 was not damaged in
the whole process of catalyst preparation.
Elemental analyses and X-ray photoelectron spectroscopy
(XPS) were used to characterise this polymeric platinum
complex. The P:Pt mole ratio of the MCM-41-2P-Pt was
determined to be 4.37. The XPS data for MCM-41-2P-Pt,
MCM-41-2P, K2PtCl4 and Pt foil are listed in Table 1. It can be
seen that the binding energies of N1s, Si2p and O1s of MCM-41-
2P-Pt are similar to those of MCM-41-2P. However, the differ-
ence of P2p binding energies between MCM-41-2P-Pt and
MCM-41-2P is 0.5 eV and the difference of Cl2p binding
energies between MCM-41-2P-Pt and K2PtCl4 is 1.6 eV. The
binding energy of Pt4f7/2 in MCM-41-2P-Pt is 0.8 eV less than
* Correspondent: E-mail: caimzhong@163.com

JOURNAL OF CHEMICAL RESEARCH 2010 649
Scheme 1
Fig. 2 Effect of reaction temperature on the yield of decyltri-
ethoxysilane.
Fig. 1 XRD profiles of the parent MCM-41 (1), MCM-41-2P (2),
and MCM-41-2P-Pt (3).
Conditions: dec-1-ene 5.0 mmol, HSi(OEt)3 5.0 mmol, catalyst
5.0 × 10−4 mmol Pt. B, 100 °C; C, 110 °C; D, 120 °C; E, 130 °C.
that in K2PtCl4, but 1.1 eV larger than that in Pt foil. These
results show that a coordination bond between P and Pt is
formed.
In order to evaluate the catalytic activity of the novel
diphosphino-functionalised MCM-41-anchored platinum
complex catalyst (MCM-41-2P-Pt), the hydrosilylation reac-
tion of olefins with triethoxysilane was studied. At first, the
catalytic activity of this supported platinum complex at differ-
ent temperatures was investigated using the hydrosilylation of
dec-1-ene with triethoxysilane as the model reaction. The
results are presented in Fig. 2. The experimental results show
that no remarkable induction period was observed, and the
reaction rate became faster with the increase in the reaction
temperature. When the hydrosilylation reaction was carried
out at 120 °C, decyltriethoxysilane was obtained in 93% yield
after 90 min. So, for the temperatures evaluated [100, 110,
120, 130 °C], 120 °C gave the best result.
Table 1 XPS data for MCM-41-2P-Pt, MCM-41-2P, K2PtCl4 and
Pt foil (in eV)a
Sample
Pt4f7/2
P2p
N1s
Si2p
O1s
Cl2p
The effect of the amount of the MCM-41-2P-Pt complex
on the hydrosilylation reaction was also investigated using
5.0 mmol of dec-1-ene as substrate at 120 °C and the results
are shown in Fig. 3. It was found that the reaction rate increased
with the increase of the amount of the catalyst, for the amounts
evaluated [1.0 × 10−4, 5.0 × 10−4, 2.0 × 10−3 mmol Pt], 5.0 ×
10−4 mmol Pt gave the best result and decyltriethoxysilane was
MCM-41-2P-Pt
MCM-41-2P
K2PtCl4
72.3 131.7 399.2 103.2 533.1 197.5
132.2 399.1 103.2 533.0
73.1
71.2
199.1
Pt foil
a The binding energies are referenced to C1s(284.6 eV), and
the energy differences were determined with an accuracy of
0.2 eV.

650 JOURNAL OF CHEMICAL RESEARCH 2010
Table 2 Catalytic activity of MCM-41-2P-Pt for the
hydrosilylation reaction of olefins with triethoxysilane
Olefin
Product a
Time Yield
/min b/%
CH3(CH2)7CH=CH2
CH3(CH2)9CH=CH2
C6H5OCH2CH=CH2
C6H5CH2CH=CH2
Cl(CH2)9CH=CH2
C6H5CH=CH2
CH3(CH2)9Si(OEt)3
CH3(CH2)11Si(OEt)3
C6H5O(CH2)3Si(OEt)3
C6H5(CH2)3Si(OEt)3
Cl(CH2)11Si(OEt)3
C6H5(CH2)2Si(OEt)3
90 93
100 91
120 80
140 71
110 94
130 66
CH2–CHCH2OCH2CH=CH2 CH2–CHCH2O(CH2)3Si(OEt)3 100 78
O
O
1
a The structure of product was further identified by H NMR.
b The yield was by calibrated GLC and no increase in yield was
observed with increasing the reaction time.
Conditions: olefin, 5.0 mmol; triethoxysilane, 5.0 mmol; MCM-
41-2P-Pt, 5.0 × 10−4 mmol; temperature, 120 °C.
Fig. 3 Effect of the amount of the catalyst on the yield of
decyltriethoxysilane.
Conditions: dec-1-ene5.0 mmol, HSi(OEt)3 5.0 mmol, reaction
temperature 120 °C
The reduction of MCM-41-2P-Pt with HSi(OEt)3, followed by
coordination with olefins provides the key intermediate (1).
Oxidative addition of HSi(OEt)3 to the intermediate (1) gives
the MCM-41-bound platinum(III) complex (2), which is fol-
lowed by insertion of the double bond to the Pt–H bond giving
the MCM-41-bound platinum(III) complex (3). The reductive
elimination of the addition products from the MCM-41-bound
platinum(III) complex (3) regenerates the intermediate (1).
This heterogeneous platinum catalyst can be easily recov-
ered by simple filtration. We also investigated the possibility to
reuse of this platinum catalyst by using the hydrosilylation of
dec-1-ene with triethoxysilane. In general, the continuous
recycle of resin-supported platinum catalysts is difficult owing
to leaching of the platinum species from the polymer supports,
which often reduces their activity within a five-recycle run.
However, when the reaction of dec-1-ene with triethoxysilane
was performed even with 0.01 mol% of MCM-41-2P-Pt, the
catalyst could be recycled 10 times without any loss of activity.
The results are summarised in Table 3. The reaction promoted
by the tenth recycled catalyst gave decyltriethoxysilane in 91%
yield (entry 2). The average yield of decyltriethoxysilane in
consecutive reactions promoted by the 1st through the 10th
recycled catalyst was 92% (entry 3). The high stability and
excellent reusable property of MCM-41-2P-Pt should result
from the chelating action of the bidentate phosphine ligand
on platinum and the mesoporous structure of the MCM-41
support. The result is important from a practical point of
view.
B, 1.0 × 10−4 mmol Pt; C, 5.0 × 10−4 mmol Pt; D,2.0 × 10−3 mmol
Pt.
obtained in 93% yield. When 2.0 × 10−3 mmol of MCM-41-
2P-Pt was used, the reaction rate was the greatest, but the final
yield of decyltriethoxysilane was only 84% and tetraethoxysi-
lane was formed in 5% yield.
Hydrosilylation reactions of a variety of olefins with
triethoxysilane were studied at 120 °C using 0.01 mol% of
MCM-41-2P-Pt as catalyst (Scheme 2),and the typical results
are listed in Table 2. As shown in Table 2, in the presence of a
catalytic amount of MCM-41-2P-Pt catalyst, hydrosilylation
reactions of dec-1-ene, dodec-1-ene and ω-chloroundec-1-ene
with HSi(OEt)3 proceeded smoothly and the corresponding
hydrosilylation products were obtained in 91–94% yields.
Speier’s catalyst (H2PtCl6) was not as effective as this when
HSi(OEt)3 was used and it was reported that the yield of
decyltriethoxysilane was only 40%.39 Under our conditions,
hydrosilylation reactions of allyl phenyl ether, allylbenzene
and allyl glycidyl ether with HSi(OEt)3 also proceeded
smoothly to give the corresponding addition products in good
yields. Hydrosilylation of styrene with HSi(OEt)3 afforded
α-adduct in 16% yield in addition to the β-adduct as a major
product.
A further objective of our studies was to determine whether
the catalysis was due to the MCM-41-2P-Pt complex or to a
homogeneous platinum complex that came off the support
during the reaction and then returned to the support at the end.
To test this, we focused on the hydrosilylation reaction of
dec-1-ene with triethoxysilane. We filtered off the MCM-41-
2P-Pt complex after 20 min of reaction time and allowed the
filtrate to react further. The catalyst filtration was performed at
the reaction temperature (120 °C) in order to avoid possible
recoordination or precipitation of soluble platinum upon cool-
ing. We found that, after this hot filtration, no further reaction
was observed.This suggests that the platinum catalyst remained
on the support at elevated temperatures during the reaction.
The heterogeneous hydrosilylation catalysed by MCM-41-
2P-Pt may proceed through a catalytic cycle analogous to that
proposed for homogeneous platinum catalysts (Scheme 3).40
Experimental
All hydrosilylation products were characterised by comparison of
their spectra and physical data with authentic samples. IR spectra
were obtained using a Perkin-Elmer 683 instrument. 1H NMR spectra
were recorded on a Bruker AC-P400 (400 MHz) spectrometer with
TMS as an internal standard in CDCl3 as solvent. Microanalyses were
obtained using a Perkin-Elmer 240 elemental analyser. X-ray photo-
electron spectroscopy (XPS) spectra were obtained using a KRATOS
XSAM 800 electron energy spectrometer. X-ray powder diffraction
patterns were obtained on a Damx-rA (Rigaka). The mesoporous
material MCM-41 was prepared according to the literature proce-
dure.41 Acetone, triethoxysilane and olefins were distilled before use
and other reagents were used as received without further purification.
Scheme 2

JOURNAL OF CHEMICAL RESEARCH 2010 651
Scheme 3
Table 3 Hydrosilylation reaction of dec-1-ene with
nitrogen for 72 h. The solid product was filtered by suction, washed
with acetone, distilled water and acetone successively and dried at
70 °C/26.7 Pa under nitrogen for 3 h to give 1.124 g of the light yellow
polymeric platinum complex (MCM-41-2P-Pt). The phosphine and
platinum content was 1.18 mmol g−1 and 0.27 mmol g−1, respectively.
triethoxysilane catalysed by recycled catalyst
Entry
Catalyst cycle
Yield /%
TON
1
2
3
1st
93
9300
10th
91
9100
Hydrosilylation of olefins with triethoxysilane
1st to 10th consecutive
av 92
total of 92000
Hydrosilylation was carried out in a 5 mL flat-bottomed flask equipped
with a magnetic stirrer and a reflux condenser to the upper of which a
drying system was attached. The olefin and the platinum complex
were stirred at the reaction temperature for 30 min before triethoxysi-
lane was added. The structure and yield of hydrosilylation products
were determined based on a standard sample and a standard curve by
GLC at regular intervals. Typical reaction conditions are as follows:
olefin 5.0 mmol, triethoxysilane 5.0 mmol, platinum complex 5.0 ×
10−4 mmol Pt. The products were isolated by distillation under reduced
pressure and characterized by IR and 1H NMR.
Preparation of MCM-41-NH2
A solution of γ-aminopropyltriethoxysilane (2.20 g, 10 mmol) in dry
chloroform (18 mL) was added to a suspension of the mesoporous
support MCM-41 (2.80 g) in dry toluene (180 mL). The mixture was
stirred for 48 h at 100 °C. Then the solid was filtered and washed by
CHCl3 (2 × 20 mL), and dried in a vacuum at 160 °C for 5 h. The
dried white solid was then soaked in a solution of Me3SiCl (4.36 g,
40 mmol) in dry toluene (150 mL) at room temperature under stirring
for 24 h. Then the solid was filtered, washed with acetone (3 × 20 mL)
and diethyl ether (3 × 20 mL), and dried in a vacuum at 120 °C for
5 h to obtain 3.54 g of hybrid material MCM-41-NH2. The nitrogen
content was found to be 1.27 mmol g−1 by elemental analysis.
Decyltriethoxysilane:42 Oil. IR (film): ν (cm−1) 2974, 2927, 2855,
1
1469, 1391, 1295, 1158, 1106, 1083; H NMR (400 MHz, CDCl3):
δ 3.81 (q, J = 7.2 Hz, 6H), 1.41–1.38 (m, 2H), 1.31–1.22 (m, 23H),
0.88 (t, J = 7.2 Hz, 3H), 0.66–0.64 (m, 2H).
Dodecyltriethoxysilane:42 Oil. IR (film): ν (cm−1) 2973, 2926, 2853,
1
1468, 1390, 1294, 1157, 1105, 1084; H NMR (400 MHz, CDCl3):
δ 3.82 (q, J = 7.2 Hz, 6H), 1.40–1.38 (m, 2H), 1.32–1.21 (m, 27H),
0.89 (t, J = 7.2 Hz, 3H), 0.67–0.64 (m, 2H).
Preparation of MCM-41-2P
A Schlenk flask was charged with paraformaldehyde (0.701 g,
23.3 mmol), dry MeOH (20 mL) and diphenylphosphine (4.340 g,
23.3 mmol). The reaction mixture was heated to 60 °C under Ar until
the white suspension formed a colourless solution. After removal of
MeOH under reduced pressure the remaining viscous oil was diluted
in dry toluene (20 mL). This solution was added to a suspension of
MCM-41-NH2 (3.020 g) in dry toluene (60 mL) and the reaction mix-
ture was heated to 105 °C under Ar for 24 h. In the cooler regions of
the flask the water-toluene azeotrope separated indicating the reaction
progress. After cooling to room temperature the solid product was
collected by filtration under Ar, washed with dry toluene (4 × 30 mL),
CH2Cl2/THF (1/1) (2 × 30 mL), CH2Cl2 (2 × 30 mL) and dried in
a vacuum (100 °C) for 5 h to give 4.08 g of the light yellow MCM-
41-2P. The nitrogen and phosphine content was found to be
0.76 mmol g−1 and 1.44 mmol g−1, respectively.
3-Phenoxypropyltriethoxysilane:43 Oil. IR (film): ν (cm−1) 3056,
2943, 2841, 1595, 1471, 1389, 1245, 1086, 753, 690; 1H NMR
(400 MHz, CDCl3): δ 7.19–7.13 (m, 2H), 6.91–6.78 (m, 3H), 3.94
(t, J = 7.6 Hz, 2H), 3.83 (q, J = 7.2 Hz, 6H), 1.83–1.78 (m, 2H), 1.23
(t, J = 7.2 Hz, 9H), 0.59–0.57 (m, 2H).
3-Phenylpropyltriethoxysilane:44 Oil. IR (film): ν (cm−1) 3058,
2980, 1594, 1576, 1494, 1465, 1390, 1107, 1067, 750, 692; 1H NMR
(400 MHz, CDCl3): δ 7.35-7.18 (m, 5H), 3.76 (q, J = 7.2 Hz, 6H),
2.64-2.61 (m, 2H), 1.75-1.72 (m, 2H), 1.19 (t, J = 7.2 Hz, 9H),
0.57-0.54 (m, 2H).
11-Chloroundecyltriethoxysilane:44 Oil. IR (film): ν (cm−1) 2977,
2927, 2856, 1441, 1391, 1297, 1167, 1104, 1081, 957, 791; 1H NMR
(400 MHz, CDCl3): δ 3.83 (q, J = 7.2 Hz, 6H), 3.42 (t, J = 6.8 Hz,
2H), 1.83–1.76 (m, 2H), 1.42–1.39 (m, 2H), 1.35–1.21 (m, 23H),
0.68–0.64 (m, 2H).
Phenylethyltriethoxysilane:45 Oil. IR (film): ν (cm−1) 3057, 2974,
1598, 1575, 1497, 1461, 1392, 1104, 1076, 752, 690; 1H NMR
(400 MHz, CDCl3): δ 7.27–7.18 (m, 5H), 3.82 (q, J = 7.2 Hz, 6H),
2.75–2.73 (m, 2H), 1.22 (t, J = 7.2 Hz, 9H), 1.01–0.97 (m, 2H).
Preparation of the MCM-41-2P-Pt complex
To a solution of K2PtCl4 (0.151 g) in acetone (40 mL) was added
MCM-41-2P (1.117 g). The mixture was heated at reflux under

652 JOURNAL OF CHEMICAL RESEARCH 2010
3-(2,3-Epoxypropoxy)propyltriethoxysilane:44 Oil. IR (film): ν
(cm−1) 2944, 2841, 1468, 1264, 1194, 1160, 1088, 910, 821; 1H NMR
(400 MHz, CDCl3): δ 3.82 (q, J = 7.2 Hz, 6H), 3.52–3.49 (m, 2H),
3.42–3.33 (m, 2H), 2.91–2.80 (m, 1H), 2.61–2.49 (m, 2H), 1.55–1.46
(m, 2H), 1.23 (t, J = 7.2 Hz, 9H), 0.58–0.56 (m, 2H).
15 Z.M. Michalska, L. Rogalski and K.R. Wijas, J. Mol. Catal. A: Chem.,
2004, 208, 187.
16 S.C. Bourque, H. Alper, L.E. Mauzer and P. Arya, J. Am. Chem. Soc., 2000,
122, 956.
17 G. Liu, B. Huang and M. Cai, React. Funct. Polym., 2007, 67, 294.
18 G. Liu and M. Cai, J. Mol. Catal. A: Chem., 2006, 258, 257.
19 H.T Yang, Z.P. Fang, X.Y. Fu and L.F. Tong, Catal. Commun., 2008, 9,
1092.
20 D. Astruc and F. Chardac, Chem. Rev., 2001, 101, 2991.
21 G.E. Oosterom, J.N.H. Reek, P.C.J. Kamer and P.W.N.M. van Leeuwen,
Angew. Chem. Int. Ed., 2001, 40, 1828.
22 M.T. Reetz, G. Lobmer and R. Schwickardi, Angew. Chem. Int. Ed., 1997,
36, 1526.
23 M.T. Reetz and D. Giebel, Angew. Chem. Int. Ed., 2000, 39, 2498.
24 C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli and J.S. Beck,
Nature, 1992, 359, 710.
25 J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge,
K.D. Schmitt, C.T.-W. Chu, D.H. Olson, E.W. Sheppard, S.B. McCullen,
J.B. Higgins and J.L. Schlenker, J. Am. Chem. Soc., 1992, 114, 10834.
26 W. Zhou, J.M. Thomas, D.S. Shephard, B.F.G. Johnson, D. Ozkaya,
T. Maschmeyer, R.G. Bell and Q. Ge, Science, 1998, 280, 705.
27 T. Maschmeyer, F. Rey, G. Sankar and J.M. Thomas, Nature, 1995, 378,
159.
28 C.-J. Liu, S.-G. Li, W.-Q. Pang and C.-M. Che, Chem. Commun., 1997,
65.
29 S.-G. Shyu, S.-W. Cheng and D.-L. Tzou, Chem. Commun., 1999, 2337.
30 M.T. Reetz and S.R. Waldvogel, Angew. Chem., Int. Ed. Engl., 1997, 36,
865.
31 M.T. Reetz, G. Lohmer and R. Schwickardi, Angew. Chem., Int. Ed. Engl.,
1997, 36, 1526.
32 T. Mizugaki, M. Murata, M. Ooe, K. Ebitani and K. Kaneda, Chem.
Commun., 2002, 52.
33 P. Arya, G. Panda, N.V. Rao, H. Alper, S.C. Bourque and L.E. Manzer,
J. Am. Chem. Soc., 2001, 123, 2889.
34 C.M.G. Hudkins, K.A. Knights, B.F.G. Johnson, Y.R. de Miguel, R. Raja
and J.M. Thomas, Chem. Commun., 2001, 2624.
35 Y. Kayaki,Y. Shimokawatoko and T. Ikariya, Adv. Synth. Catal., 2003, 345,
175.
Conclusion
In conclusion, we have described a novel diphosphino-
functionalised MCM-41 anchored platinum complex whose
preparation is simple and convenient. This platinum complex
has not only high activity for the hydrosilylation of olefins
with triethoxysilane, but offers practical advantages such as
easy handling, separation from the product and reuse.
This work was supported by the Natural Science Foundation of
Jiangxi Province of China (Project No. 2008GQH0034)
Received 19 August 2010; accepted 28 September 2010
Paper 1000306 doi: 10.3184/030823410X12887259824283
Published online: 24 November 2010
References
1
I. Ojima, S. Patai and Z. Rappaport, The chemistry of organic silicon
compounds, Wiley-Interscience, New York, Chap. 25, 1989, p.1479.
B. Marciniec, Coordin. Chem. Rev., 2005, 249, 2374.
M. Tanabe, D. Ito and K. Osakada, Organometallics, 2007, 26, 459.
J.L. Speier, J.A. Webster and C.H. Barnes, J. Am. Chem. Soc., 1957, 57,
974.
2
3
4
5
6
E. Louis, I. Jussofie, F.E. Kuhn and W.A. Herrmann, J. Organomet. Chem.,
2006, 691, 2031.
H. Maciejewski, B. Marciniec and I. Kownacki, J. Organomet. Chem.,
2000, 597, 175.
36 H. Zhao, Y. Wang, J. Sha and M. Cai, Tetrahedron, 2008, 64, 7517.
37 M. Cai, G. Zheng, L. Zha and J. Peng, Eur. J. Org. Chem., 2009, 1585.
38 M. Cai, G. Zheng and G. Ding, Green Chem., 2009, 11, 1687.
39 M. Capka and J. Hetflejs, Collect. Czech. Chem. Commun., 1974, 39, 154.
40 A.J. Chalk and J.F. Harrod, J. Am. Chem. Soc., 1965, 87, 16.
41 M.H. Lim and A. Stein, Chem. Mater., 1999, 11, 3285.
42 H.H. Szmant, G.W. Miller, J. Makhlouf and K.C. Schreiber, J. Org. Chem.,
1962, 27, 261.
7
8
9
A. Corma and H. Garcia, Chem. Rev., 2002, 102, 3837.
A. Corma, H. Garcia and A. Leyva, J. Catal., 2006, 240, 87.
T. Onoe, S. Iwamoto and M. Inoue, Catal. Commun., 2007, 8, 701.
10 R. Drake, R. Dunn and D.C. Sherrington, Chem. Commun., 2000, 1931.
11 R. Drake, D.C. Sherrington and S.J. Thomson, React. Funct. Polym., 2004,
60, 65.
12 R. Drake, R. Dunn and D.C. Sherrington, J. Mol. Catal. A: Chem., 2001,
177, 49.
43 J.-Z. Yao, Y.-Y. Chen and B.-S. Tian, J. Organomet. Chem., 1997, 534, 51.
44 Y.-Y. Chen, X.-R. Lu and Z.-Y. Wang, Chin. J. Catal., 1990, 11, 75.
45 L.N. Lewis, J. Am. Chem. Soc., 1990, 112, 5999.
13 M. Okamoto, H. Kiya and H. Yamashita, Chem. Commun., 2002, 1634.
14 Q.J. Miao, Z.P. Fang and G.P. Cai, Catal. Commun., 2003, 4, 637.

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