C–C Cross-Coupling Reactions of Organosilanes with Terminal Alkenes and Allylic Acetates Using PdII Catalyst Supported on Starch Coated Magnetic Nanoparticles

Article abstract of DOI:10.1002/ejoc.201901812

Starch coated magnetic nanoparticles supported palladium catalyst has been explored to perform C–C cross coupling reactions, such as oxidative Heck coupling and Tsuji–Trost allylic coupling using organosilicon compounds as one of the coupling partners. The biopolymer coated magnetic catalyst was very easy to recover magnetically and was efficiently recycled in the subsequent batches. All the reactions were performed in air and thus the necessity of air and moisture free reaction condition is avoided. The present protocols show wide substrate scope and good yields of the products.

Full text of DOI:10.1002/ejoc.201901812

A Journal of
Accepted Article
Title: C-C cross-coupling reactions of organosilanes with terminal
alkenes and allylic acetates using Pd(II) catalyst supported on
starch coated magnetic nanoparticles
Authors: Debabrata Patra, Subir Panja, and Amit Saha
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To be cited as: Eur. J. Org. Chem. 10.1002/ejoc.201901812
Link to VoR: http://dx.doi.org/10.1002/ejoc.201901812
Supported by

10.1002/ejoc.201901812
European Journal of Organic Chemistry
COMMUNICATION
C-C cross-coupling reactions of organosilanes with terminal
alkenes and allylic acetates using Pd(II) catalyst supported on
starch coated magnetic nanoparticles
Debabrata Patra,[a] Subir Panja,[b] and Amit Saha*[a]
[a]
Dr. A. Saha, Mr. D. Patra
Department of Chemistry
Jadavpur University
Kolkata 700032, India
E-mail: amit.saha@jadavpuruniversity.in
Mr. S. Panja
[b]
School of Chemical Sciences
Indian Association for the Cultivation of Science
Kolkata 700032, India
Supporting information for this article is given via a link at the end of the document.
Abstract: Starch coated magnetic nanoparticles supported
palladium catalyst has been explored to perform C-C cross coupling
reactions, such as oxidative Heck coupling and Tsuji-Trost allylic
coupling using organosilicon compounds as one of the coupling
partners. The biopolymer coated magnetic catalyst was very easy to
recover magnetically and was recycled efficiently in the subsequent
batches. All the reactions were performed in air and thus necessity
of air and moisture free reaction condition is avoided. The present
protocols show wide substrate scope and good yields of the
products.
sciences for different purposes like drug delivery, tumor
targeting, magnetic resonance imaging etc. We have explored
the starch coated magnetic Fe3O4 nanoparticles to immobilize
the Pd(II) catalyst on the surface of the nanoparticles. The
synthesized magnetic palladium nano-catalyst has been tested
to catalyze the C-C cross coupling reactions of organosilanes
with alkenes and allylic acetates. Various terminal alkenes
underwent smooth C(sp2)-H arylation by aryltrimethoxysilanes in
presence of magnetic-Pd(II) catalyst, tetrabutylammonium
fluoride (TBAF) and p-benzoquinone (BQ) as the oxidizing agent
in open air condition (Scheme 1). C-C cross-coupling of allylic
acetates were also performed with organosilanes using
magnetic-Pd(II) catalyst and TBAF in aerial atmosphere
(Scheme 1).
Introduction
The pioneering route for constructing C-C bonds involves the
cross-coupling reactions using various organometallic and
organometalloid reagents. Heck coupling and Tsuji-Trost
coupling are two important tools for C-C bond formations leading
to total synthesis of many natural products and biologically
active organic compounds.[1] The oxidative Heck reaction has
recently gained more attention mainly because of air and
moisture insensitive reaction conditions using organoboron,[2]
organotin[3] and organosilicon[4] reagents as the coupling
partners. Among common organometallic reagents organosilicon
compounds are attractive due to their stability, low toxicity, low-
cost and high natural abundance of silicon.[5] Although,
organosilicon compounds have been employed in oxidative
Heck coupling reaction for a number of times,[4] but the use of
expensive non-recyclable homogeneous catalysts makes them
economically less potent. In this report, we demonstrate the use
of magnetic heterogeneous catalyst to carry out the oxidative
Heck coupling reactions of organosilane compounds with
terminal alkenes in aerial condition. Organosilanes have also
been used in this study to perform Tsuji-Trost allylation reactions
with allylic acetates in presence of magnetic nano-catalyst.
Heterogeneous magnetic catalysts[6] have become popular
due to easy magnetic separation of the catalyst from the
reaction mixture. Additionally, the heterogeneous catalysts with
good recyclability offer economic sustainability. Here, we have
used the starch coated magnetic ferrite nanoparticles as the
heterogeneous support of Pd(II) catalyst. The starch coated
Fe3O4 nanoparticles[7] have extensively been used in biomedical
Scheme 1. Pd(II) catalyzed C-C cross coupling reactions of organosilanes
with terminal alkenes and allylic acetates.
Results and Discussion
The starch coated magnetic ferrite nanoparticles were prepared
following the similar methods reported earlier.[7a - 7c] The Fe3+ and
Fe2+ salts were dissolved in an aqueous solution of starch by
heating at 60 oC. Black colored starch coated Fe3O4
nanoparticles were started to appear upon addition of aqueous
ammonia solution. The black nanoparticles were centrifuged,
washed with acetone and dried under vacuum. The Pd(II) was
immobilized on the surface of starch coated Fe3O4 nanoparticles
by stirring the methanolic suspension of the nanoparticles with
PdCl2 at room temperature for 15 h. The sizes of the Pd(II)
immobilized starch coated magnetic nanoparticles were checked
by TEM (transmission electron microscopy) experiment and it
was found to be 7 - 19 nm (Fig. 1). The surface morphology and
the amount of palladium in the supported catalyst were
determined by SEM (scanning electron microscope) (Fig. 2)
along with the EDX (Energy Dispersive X-ray) (Fig. 3)
1
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experiments. The weight percentage of palladium in the
supported magnetic catalyst is found to be 4.92 as per the EDX
elemental compositional analysis (Fig. 3, elemental analysis
table). The weight% of palladium was also verified by ICP-AES
analysis and it was found to be 4.95 which is very close to the
result as obtained from EDX experiment.
The BET (nitrogen adsorption isotherms) experiment shows, the
specific surface area of the catalyst is 10 m2/gm (Figure is
included in the Supporting Information). The thermal stability of
the catalyst was examined by TGA analysis (Fig. 4) which
reveals a gradual weight loss due to removal of physically
adsorbed solvent molecules[6i] below 200 oC. The weight loss
around 300 - 350 oC may be due to the loss of surface hydroxyl
groups.
Figure 1. TEM image of the Pd(II) nano-catalyst [Fe3O4-starch-Pd(II)].
Figure 4. TGA analysis of the catalyst [Fe3O4-starch-Pd(II)].
The oxidative Heck coupling reaction was performed by
simple experimental procedure. The solution of terminal alkene
and organosilane (1.5 equiv.) in THF solvent was stirred at 40 oC
in presence of p-benzoquinone (BQ), tetrabutylammonium
fluoride (TBAF) and Pd(II) magnetic catalyst (Fe3O4-starch-
Pd(II)) under aerial atmosphere for a certain time period. Upon
completion of reaction (monitored by TLC), the catalyst was
separated magnetically and the desired product was obtained by
usual work-up followed by column chromatographic purification.
The reaction condition was optimized by performing a set
of reactions between butyl acrylate and phenyltrimethoxysilane
with variation of different reaction parameters (Table 1). The
coupling between butyl acrylate and phenyltrimethoxysilane was
first tried using Fe3O4-starch-Pd(II) catalyst in presence of p-
benzoquinone (BQ) and TBAF in DMF solvent (entry 1, Table 1).
However, the yield was not satisfactory (48%). Other common
solvents like DMSO, water, acetonitrile (entries 2 - 4, Table 1)
were also not suitable for the coupling reaction. The reaction
was found to proceed efficiently in presence of Fe3O4-starch-
Pd(II) catalyst, p-benzoquinone oxidant and TBAF in THF
Figure 2. SEM image of the Pd(II) nano-catalyst [Fe3O4-starch-Pd(II)].
o
medium under aerial condition at 40 C to produce the desired
product with 80% of yield in 12 h of reaction time period (entry 5,
Table 1).The reaction remained incomplete within 10 h of time
period (entry 7, Table 1). However, the yield of the reaction did
not improve prolonging the reaction time period beyond 12 h. In
presence of DDQ as the oxidizing agent, a complex reaction
mixture was obtained with the formation of several unidentified
side-products (entry 8, Table 1). The crucial role of p-
benzoquinone oxidant in the coupling reaction of butyl acrylate
and phenyltrimethoxysilane was established by the control
experiment (entry 9, Table 1) which produces the desired
product only in 26% of yield in absence of p-benzoquinone. The
reaction did not initiate at all without the Pd-catalyst. Other
magnetic palladium catalyst, such as Fe3O4-Dopamine-Pd(II)[6a]
was not found suitable for the reaction and produced the desired
Element
C K
O K
Pd L
Fe K
Weight %
15.06
38.09
4.92
41.93
Atomic %
28.42
53.46
1.05
17.07
Figure 3. Energy Dispersive X-ray spectrum (EDX) and the elemental analysis
table of the Pd(II) nano-catalyst [Fe3O4-starch-Pd(II)].
2
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product only in 13% of yield (entry 10, Table 1). Some non-
This result motivated us to explore the Pd-magnetic
catalyst in organosilicon compound mediated Tsuji-Trost
allylation[9] reaction of cinnamyl acetate. It was found that
cinnamyl acetate undergoes Tsuji-Trost cross-coupling reaction
with phenyltrimethoxysilane efficiently to provide the desired
coupling product, 1,3-diphenyl propene in good yield (84%)
(entry 1, Table 3) in presence of Fe3O4-starch-Pd(II) catalyst and
[8b]
magnetic heterogeneous catalysts (Cellulose-Pd[8a], Pd/Al2O3
)
were also found to be nonfunctional to catalyze the coupling
reaction between butyl acrylate and phenyltrimethoxysilane
(entries 11, 12, Table 1).
Table 1. Optimization of the reaction condition for oxidative Heck coupling
reaction.[a]
Table 2. Oxidative Heck coupling using aryltrimethoxysilanes.[a]
[a] Reaction condition: Butyl acrylate (51 mg, 0.4 mmol), phenyl
trimethoxysilane (120 mg, 0.6 mmol), catalyst (7 mg), BQ (64 mg, 0.6 mmol),
TBAF (1 M Solution in THF, 0.6mL, 0.6 mmol) in THF (2 mL), at 40 oC for 12h.
The optimized reaction protocol (entry 5, Table 1) was
explored to perform a series of oxidative coupling reactions
(Table 2). Various electron deficient alkenes such as methyl
acrylate, ethyl acrylate, butyl acrylate and acrylonitrile underwent
oxidative C-H arylation reactions with the organosilicon
compounds to produce the desired coupling products in good
yields (3a - 3c, 3e, 3j, Table 2). Styrene, 4-fluorostyrene, 3-
methylstyrene and 4-methylstyrene were also employed in the
oxidative cross coupling reactions resulting the products 3d, 3f -
3h, 3k (Table 2) satisfactorily.
Under the similar reaction condition, allyl acetate produces
1,3-diphenyl propene (43%) along with trace amount of cinnamyl
acetate in presence of 1.5 equivalent of phenyltrimethoxysilane
in 14 h of time period (reaction 1, Scheme 2). However, the
same reaction produces cinnamyl acetate (30%) and trace
amount 1,3-diphenyl propene within 3 h of time period (reaction
2, Scheme 2). With time, the amount of 1,3-diphenyl propene
gradually increases in the reaction mixture and the concentration
of cinnamyl acetate decreases. Thus, allyl acetate participates in
cascade oxidative coupling followed by Tsuji-Trost allylation
reaction. In presence of large excess of phenyltrimethoxysilane
(3 equivalent), exclusive formation of 1,3-diphenyl propene was
obtained in good amount (69%) within 14 h of time period (entry
9, Table 2) via the cascade oxidative coupling and allyl-aryl
cross coupling reactions.
[a] Reaction condition: alkene (0.4 mmol), aryltrimethoxysilane (0.6 mmol), Pd-
catalyst (7 mg, 0.8 mol%), BQ (64 mg, 0.6 mmol), TBAF (1 M Solution in THF,
0.6 mL, 0.6 mmol) in THF (2 mL), at 40 oC for certain time period. [b] Yields
are isolated yields. [c] The reaction was performed using 1.2 mmol (3 equiv.)
of phenyltrimethoxysilane.
Scheme 2. Reactions of allyl acetate with phenyltrimethoxysilane.
TBAF in THF solvent at 60 oC under open aerial condition. Tsuji-
Trost allylic couplings were performed with a series of cinnamyl
acetate derivatives using various organosilane compounds
(Table 3). The substituents like o-Me, p-Me, o-OMe, m-OMe, p-F,
3
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COMMUNICATION
p-Cl (entries 2 - 6, 8 - 10, Table 3) present in the aromatic ring of
cinnamyl acetates remain unaltered under the present reaction
condition. In case of p-chlorocinnamyl acetate, the C(sp2)-Cl
functionality did not involve in C-C cross coupling with
phenyltrimethoxysilane and selective allyl-aryl cross coupling
occurred to provide the desired 1,3-diaryl propene (5h) product
in good yield (86%) (entry 10, Table 3) under the present
geometry (C), via the well-known 1--alkyl complex (B)[10] and
reductive elimination from the more stable trans-intermediate (C)
produces trans-1,3-diphenylpropene (3i) as the sole product.
The allylic coupling reaction between cinnamyl acetate and
phenyltrimethoxysilane (entry 1, Table 3) was chosen to perform
the hot filtration test for checking the heterogeneity of the
magnetic catalyst during the course of the reaction. The reaction
was observed to be arrested completely upon removal of the
magnetic catalyst after an intermediate time period (1 h) and it
proves the absence of palladium in the solution phase of the
reaction mixture. Thus, starch binds the palladium firmly on the
surface of the magnetic nanoparticles and prevents the leaching
of palladium into the solution.
Table 3. Tsuji-Trost allylic couplings using organosilane compounds.[a]
Upon completion of the reaction, the magnetic palladium
catalyst can be recovered easily from the reaction mixture with
the aid of an external magnet (Fig. 5). After washing the catalyst
with acetone and drying under vacuum, the catalyst was used in
the next batch of reaction efficiently.
[a] Reaction condition: allylic acetate (0.4 mmol), organosilicon compound (0.6
mmol), Pd-catalyst (7 mg, 0.8 mol%), TBAF (1 M Solution in THF, 0.6mL, 0.6
mmol) in THF (2 mL), at 60 oC for certain time period. [b] Yields are isolated
yields.
Figure 5. Magnetic separation of Fe3O4-starch-Pd(II) catalyst by an external
magnet.
reaction condition. The vinyltrimethoxysilane was also found
reactive to transfer the vinyl group resulting the formation of 1,4-
diene product (5i) in 74% yield (entry 11, Table 3). Interestingly,
the cis-cinnamyl acetate undergoes Tsuji-Trost coupling with
phenyltrimethoxysilane (entry 7, Table 3) to provide trans-1,3-
diphenylpropene (3i) exclusively. This result suggests the
formation of --allyl complex of palladium (A) as the key
intermediate (Scheme 3) which equilibrates with its trans-
In the cross-coupling reaction of butyl acrylate with
phenyltrimethoxysilane, the magnetic catalyst was recycled
efficiently for 4 times without much loss of catalytic activity. The
yield of desired product, 3a was 78% at the 4th cycle of reaction
(Fig. 6). However, the yield gradually decreases beyond 4th cycle
and it was 68% at 6th cycle of reaction (Fig. 6).
Figure 6. The catalyst recyclability chart.
Scheme 3. Formation of trans-1,3-diphenylpropene from cis-cinnamyl acetate
via --allyl complex.
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Conclusions
Conflict of Interest
In conclusion, efficient protocols for C-C cross coupling
reactions such as oxidative Heck coupling and Tsuji-Trost
allylation have been developed using organosilicon compounds
as aryl donors and heterogeneous magnetic palladium catalyst.
The biopolymer (starch) coated magnetic nanoparticles were
used as the heterogeneous support for palladium catalyst which
is easy to recover and shows good recyclability. The catalyst
allows the reactions to proceed under open aerial condition and
thus avoids the necessity of moisture and oxygen free inert
The authors declare no conflict of interest.
Acknowledgements
Debabrata Patra is thankful to CSIR-India for his JRF fellowship.
We are pleased to acknowledge UGC-BSR Start-up grant (FD
Diary No.4855; Dated: 24.09.2018) for the financial support. We
also acknowledge RUSA 2.0 research grant from Jadavpur
University, UGC-CAS program in Chemistry, Jadavpur
University and the DST-PURSE Program at Jadavpur University.
atmosphere.
Catalyst reusability, air compatibility and good
yields of the products make the protocols economically
sustainable.
Experimental Section
Keywords: Magnetic palladium catalyst • Oxidative Heck
coupling • Tsuji-Trost allylic coupling • Organosilicon compounds
• Recyclable catalyst
General experimental procedures:
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Representative experimental procedure for oxidative-Heck
coupling reaction of n-butyl acrylate with phenyl
trimethoxysilane (entry 1, Table 2). A mixture of n-butyl
acrylate (0.051 g, 0.4 mmol), phenyltrimethoxysilane (0.120 g,
0.6 mmol), Pd-catalyst (7 mg, 0.8 mol%), TBAF (1M solution in
THF, 0.6 mL, 0.6 mmol), and BQ (0.064 g, 0.6 mmol), in THF (2
ml), was stirred at 40 oC for 12 h under aerial atmosphere. The
progress of the reaction was monitored by TLC. After completion
of the reaction the Pd-catalyst was separated by an external
magnet and the crude product was obtained by usual work- up
using EtOAc. The crude product was purified by column
chromatography over silica gel using petroleum ether-ethyl
acetate (97:3) solvent mixture. The desired product, n-butyl
cinnamate (3a) was obtained as colorless oil (65 mg, 80%).
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Representative experimental procedure for Tsuji-Trost
coupling of cinnamyl acetate with phenyltrimethoxysilane
(entry 1, Table 3). A mixture of cinnamyl acetate (0.070 g, 0.4
mmol), phenyltrimethoxysilane (0.120 g, 0.6 mmol), Pd- catalyst
(7 mg, 0.8 mol%) and TBAF (1 M solution in THF, 0.6 mL, 0.6
mmol) in THF (2 mL) was stirred at 60 oC for 4 h under air
atmosphere. The reaction was monitored by TLC. After catalyst
separation by external magnet, the reaction mixture was
worked-up by usual procedure using ethyl acetate. The crude
product was purified by column chromatography over silica gel
using petroleum ether-ethyl acetate (99:1) solvent mixture to get
the desired product, 1,3-diphenyl propene (3i) as a colorless oil
(65.4 mg, 84%).
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This procedure is followed for preparation of other compounds
(5a - 5i) listed in Table 3.
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Entry for the Table of Contents
Key Topic: Magnetic Pd-Catalyst
Magnetically retrievable palladium nano-catalyst has been used in Oxidative Heck coupling and Tsuji-Trost allylic coupling reactions
using organosilicon compounds as the aryl donors under open aerial condition. The magnetic catalyst is easily recovered and
recycled efficiently. Wide substrate scope and good yields of the products were obtained in both the cases.
7
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