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Heck coupling reaction using monomeric ortho-palladated complex of 4-methoxy- benzoylmethylenetriphenylphosphorane under microwave irradiation.

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Full Paper
Received: 23 February 2010
Revised: 18 May 2010
Accepted: 20 May 2010
Published online in Wiley Online Library: 23 August 2010
(wileyonlinelibrary.com) DOI 10.1002/aoc.1705
Heck coupling reaction using monomeric
ortho-palladated complex of 4-methoxybenzoylmethylenetriphenylphosphorane
under microwave irradiation
Abdol R. Hajipoura,b∗ , Kazem Karamia and Ghazal Tavakolia
The activity of [Pd(C6 H4 CH2 NH2 -κ 2 -C-N)PPh3 MOBPPY]OTf complex, A (MOBPPY = 4-methoxybenzoylmethylenetriphenylphosphoraneylide), was investigated in the Heck–Mizoroki C–C cross-coupling reaction under conventional heating and
microwave irradiation conditions. The complex is an active and efficient catalyst for the Heck reaction of aryl halides. The yields
were excellent using a catalytic amount of [Pd(C6 H4 CH2 NH2 -κ 2 -C-N)PPh3 MOBPPY]OTf complex in N-methyl-2-pyrrolidinone
(NMP) at 130 ◦ C and 600 W. In comparison to conventional heating conditions, the reactions under microwave irradiation gave
c 2010 John Wiley & Sons, Ltd.
higher yields in shorter reaction times. Copyright Keywords: orthopalladate; Heck reaction; catalyst; microwaves
Introduction
798
Because of the many applications of carbon–carbon bond
formation in the areas of bioactive compounds, natural products
and high performance materials[1] over the past few years, the
C–C coupling reactions have become a versatile tool in organic
synthesis.[2 – 4] One of the most efficient methods in the formation
of the C(sp2) –C(sp2) bond is the Heck reaction,[5 – 7] in which a
palladium-catalyzed reaction is carried out between an olefin and
an aryl, alkenyl halide or triflate in the presence of a base. This
reaction was discovered independently by Heck[8] and Mizoroki[9]
about 40 years ago and is generally catalyzed in the solution by
palladium species generated from either Pd(0) complexes or Pd(II)
salts.[10] As the Heck reaction is one of the most promising metalcatalyzed syntheses[11] of monomers, pharmaceuticals, sunscreen
agents and herbicides, considerable efforts have recently been
devoted to finding new catalytic systems and methodologies to
improve the reaction conditions. However, to develop efficient
methods for these reactions, the catalyst should be chosen
properly and most researches have focused on finding efficient
catalytic systems with higher activity and stability. Among the new
methods the palladacycle catalysts are the most important class
of catalyst; these complexes have been known for over 30 years
and the Heck reaction has been performed with activated and
non-activated aryl halides using very low concentrations of these
catalysts.
Microwave irradiation methodology has advantages in organic
and inorganic synthesis such as greater energy efficiency and
higher reaction rates, and in many cases improved yields in
comparison to the conventional conditions.[12] The reaction rate
improvement could be explained by considering the higher and
more rapid temperature homogeneity reached by employing
microwave (MW) heating methods.[13] Although in conventional
heating methods the vessel is heated and then the heat transfers
by convention, in MW-assisted reactions molecules are directly
Appl. Organometal. Chem. 2010, 24, 798–804
kinetically/thermally activated.[14] This rapid in situ heating is called
the superheating effect.[15]
Application of MW irradiation as an efficient heating source was
reported as early as the 1940s,[16] and the first application of this
synergy source in organic synthesis was reported in 1986 by Gedye
and Giguere.[17,18] In 1996, Hallberg and co-workers applied this
method in the Heck cross coupling reaction.[19]
Herein, in continuation of our previous work on palladacycle systems and microwave assisted reactions,[20 – 25]
we wish to report the application of [Pd(C6 H4 CH2 NH2 κ 2 -C-N)PPh3 MOBPPY]OTf complex, A (MOBPPY = 4-meth
oxybenzoylmethylenetriphenylphosphoraneylide), as a thermally
stable and oxygen insensitive catalyst[26] for Heck coupling reaction of various types of aryl halides under both traditional heating
and microwave irradiation conditions (Scheme 1).
Results and Discussion
Initially, the Heck cross-coupling reaction conditions using
[Pd(C6 H4 CH2 NH2 -κ 2 -C-N)PPh3 MOBPPY]OTf complex were optimized for the reaction of iodoanisole and methylacrylate using
0.2 mol% catalyst, various bases and solvents under microwave
irradiation (600 W, 130 ◦ C). As demonstrated in Table 1 (entry 4),
K2 CO3 as base and 1-methyl-2-pyrolidinone (NMP) as solvent gave
the best results.
∗
Correspondence to: Abdol R. Hajipour, Pharmaceutical Research Laboratory,
Department of Chemistry, Isfahan University of Technology, Isfahan 84156,
I. R. Iran. E-mail: haji@cc.iut.ac.ir
a Pharmaceutical Research Laboratory, Department of Chemistry, Isfahan
University of Technology, Isfahan 84156, I. R. Iran
b Department of Pharmacology, University of Wisconsin, Medical School, 1300
University Avenue, Madison, WI 53706-1532, USA
c 2010 John Wiley & Sons, Ltd.
Copyright Heck coupling with monomeric ortho-palladated complex of MOBPPY
NH2
Pd
Cl
1/2
+PPh3
Cl
NH2
Pd
Pd
H2N
Cl
PPh3
Ye =4-methoxybenzoylmethylenetriphenylphosphorane ylide (MOBPPY)
i)+AgOTf, THF or Me2CO
ii)-AgCl
iii)+Ye
Scheme 1. Synthesis of Palladacycle Complex [Pd (C6 H4 CH2 NH2 -κ 2 -C-N)PPh3 MOBPPY]OTf.
Table 1. Optimization of base and solvent under microwave
irradiationa
Entry
1
2
3
4
5
6
7
Base
Solvent
Temperature
(◦ C)
Time
(min)
Conversion (%)
Et3 N
Cs2 CO3
Na2 CO3
K2 CO3
K2 CO3
K2 CO3
K2 CO3
NMP
NMP
NMP
NMP
DMF
CH3 CN
Toluene
130
130
130
130
130
130
130
2
2
2
2
2
2
2
0
70
Trace
95
75
0
0
a Reaction conditions: 2 mmol aryl halide, 5 mmol olefin, 2.2 mmol
K2 CO3 , 0.2 mol% palladacycle A.
Appl. Organometal. Chem. 2010, 24, 798–804
Mol%
catalyst
None
0.01
0.02
0.05
0.1
0.2
0.4
0.6
Time (min)
Temperature (◦ C)
Conversion (%)
2
2
2
2
2
2
2
2
130
130
130
130
130
130
130
130
0
30
50
85
95
95
98
100
a Reaction
conditions: 2 mmol aryl
2.2 mmol K2 CO3 , and palladacycle A.
halide,
5 mmol
olefin,
conventional heating and microwave irradiation, as shown in
Tables 3 and 4.
The results showed that aryl halides with either electronwithdrawing or electron-donating substituents reacted with
olefins rapidly and generated the coupled products with excellent
yields. We also tried these reactions employing styrene as the
olefin under both microwave irradiation and traditional heating
c 2010 John Wiley & Sons, Ltd.
Copyright wileyonlinelibrary.com/journal/aoc
799
We also optimized the concentration of catalyst, employing
various amounts of catalyst for the reaction of iodoanisole and
methylacrylate using K2 CO3 as base and NMP as solvent. The
data clearly showed that 0.1 mol% of catalyst gave the highest
yields (Table 2). As this catalyst is not sensitive to oxygen,
the reactions were carried out under an air atmosphere. We
applied these conditions for Heck cross-coupling reaction of
different types of aryl halides with methylacrylate under both
Table 2. Optimization of catalyst concentration under microwave
irradiationa
A. R. Hajipour, K. Karami and G. Tavakoli
Table 3. Heck reaction of aryl halides under conventional heating conditions in an oil batha
Time
(h)
Conversion
(%)
Yieldb
(%)
1
2.5
100
91
2
7
90
84
3
1.5
100
92
4
1.5
100
94
5
6.5
100
90
6
1.75
100
89
7
3
100
90
8
3
100
93
9
8
90
85
10
1.75
100
93
11
9.5
90
83
12
8
85
78
Entry
a
b
ArX
R CH CH2
Product
Reaction conditions: 2 mmol aryl halide, 5 mmol olefin, 2.2 mmol K2 CO3 , 0.1 mol% palladacycle A and temperature 130 ◦ C, 600 W.
Isolated yield.
800
conditions (Tables 3 and 5). We found that, in comparison to
the heating conditions, the microwave irradiation reduced the
reaction times from hours to minutes. Also, the results listed
in Tables 4 and 5 clearly show that the coupling reactions with
methylacrylate as the olefin were faster than styrene. In the case of
wileyonlinelibrary.com/journal/aoc
1-bromo-3-chlorobenzene, although this procedure could activate
the C–Cl bond, by using stoichiometric amount of olefins only the
Br was substituted in each case, which may be due to the higher
activity of Br compared with Cl [21]. In all of the reactions, only the
trans isomers were produced. Furthermore as shown in Table 4
c 2010 John Wiley & Sons, Ltd.
Copyright Appl. Organometal. Chem. 2010, 24, 798–804
Heck coupling with monomeric ortho-palladated complex of MOBPPY
Table 4. Microwave assisted Heck reaction of aryl halides with methylacrylatea
Time
(min)
Conversion
(%)
Yieldb
(%)
1
1
100
93
2
1
100
94
3
4
100
93
4
6
100
90
5
1
100
94
6
6
100
91
7
10
90
84
8
10
90
84
9
40
88
81
10
13
100
89
11
4
100
93
12
20
90
82
Entry
a
b
ArX
Product
Appl. Organometal. Chem. 2010, 24, 798–804
c 2010 John Wiley & Sons, Ltd.
Copyright wileyonlinelibrary.com/journal/aoc
801
Reaction conditions: 2 mmol aryl halide, 5 mmol olefin, 2.2 mmol K2 CO3 , 0.1 mol% palladacycle A, temperature 130 ◦ C and 600 W.
Isolated yield.
A. R. Hajipour, K. Karami and G. Tavakoli
Table 5. Microwave assisted Heck reaction of aryl halides with styrenea
Time
(min)
Conversion
(%)
Yieldb
(%)
1
1
100
95
2
2
100
94
3
12
100
96
4
18
98
92
5
6
100
96
6
17
85
80
7
18
90
83
8
10
98
92
9
30
97
91
10
40
85
78
11
6
100
92
12
25
87
80
Entry
a
b
ArX
Product
Reaction conditions: 2 mmol aryl halide, 5 mmol olefin, 2.2 mmol K2 CO3 , 0.001 mmol palladacycle A and temperature 130 ◦ C and 600 W.
Isolated yield.
802
wileyonlinelibrary.com/journal/aoc
c 2010 John Wiley & Sons, Ltd.
Copyright Appl. Organometal. Chem. 2010, 24, 798–804
Heck coupling with monomeric ortho-palladated complex of MOBPPY
(entries 11 and 12) and Table 5 (entries 11 and 12), this method
can be used for the Heck reaction of even less reactive aryl chloride
derivatives with longer reaction times.
Conclusion
In summary, here we repot a highly active and efficient catalyst for
promoting the Heck cross-coupling reaction of various aryl halides
with olefins to produce the corresponding products in excellent
yields and high chemoselectivity in short reaction times. Reactions
were carried out under both conventional heating and microwave
irradiation conditions. The results showed that under microwave
irradiation conditions, the reactions were completed in shorter
reaction times.
Experimental
General
trans-4-Methoxystilbene (entry 3, Table 3 and entry 3, Table 5)
M.p. 135.5–137.1 ◦ C;[27] found 131–135 ◦ C.1 H NMR (400 MHz,
CDCl3 ): δ = 7.50–7.46 (m, 4H), 7.38–7.36 (br t, 3H), 7.11 (d,
1H, J = 16.4 Hz), 7.01 (d, 1H, J = 16.4 Hz), 6.93 (d, 2H, J = 8.4 Hz),
3.85 (s, 3H). 13 C NMR (100 MHz, ppm, CDCl3 ): δ = 159.6, 137.7,
130.1, 130.0, 129.8, 128.5, 128.4, 127.7, 127.4, 127.2, 126.6, 126.5,
114.2, 114.1, 55.2. IR (KBr, cm−1 ): ν 3055, 2963, 1580.
trans-4-Cyanostilbene (entry 7, Table 3 and entry 4, Table 5)
M.p. 117–119 ◦ C;[28] found 115–118 ◦ C. 1 H NMR (400 MHz, CDCl3 ):
δ = 7.65 (d, 2H, J = 8.2 Hz, Ph), 7.60 (d, 1H, J = 8 Hz, Ph), 7.55 (d,
2H, J = 7.2 Hz, Ph), 7.41 (t, 2H, J = 7.2 Hz), 7.34–7.35 (br d, 2H,
Ph), 7.23 (d, 1H, J = 16.2 Hz, CH), 7.10 (d, 1H, J = 16.4 Hz, CH). 13 C
NMR (100 MHz, ppm, CDCl3 ): δ = 141.9, 136.3, 132.5, 132.4, 128.9,
128.7, 128.5, 127.9, 127.5, 127.2, 126.9, 126.8, 126.7, 119.5, 110.8.
IR (KBr, cm−1 ): ν 3044, 2924, 2226, 1602.
1 H-NMR
spectra were recorded using 500 and 400 MHz and
C-NMR spectra were recorded using 125 and 100 MHz in CDCl3
solutions at room temperature on a Bruker Avance 500 instrument
(Rheinstetten, Germany) and Varian 400 NMR (TMS was used
as an internal standard). The FT-IR spectra were recorded on a
spectrophotometer (Jasco-680, Japan). We used the Milestone
Microwave (Microwave Labstation) for synthesis. All chemicals
were purchased from Merck and Aldrich and were used as received.
The reactions were carried out in N-methyl-2-Pyrrolidinone (NMP)
at 130 ◦ C 600 W microwave irradiation or at 130 ◦ C under heating
conditions using an oil bath.
13
Synthesis of Palladacycle Complex [Pd(C6 H4 CH2 NH2 -κ 2 -CN)PPh3 MOBPPY]OTf (A)
[Pd(C6 H4 CH2 NH2 -κ 2 -C-N)PPh3 MOBPPY]OTf as a palladacycle complex was prepared according to our previous work.[26]
Methyl trans-3-chlorocinnamate (entry 4, Table 3 and entry 5, Table 4)
H NMR (400 MHz, CDCl3 ): δ = 7.64 (d, 1H, J = 16 Hz, CH),
7.53–7.52 (br t, 1H, Ph), 7.41–7.25 (m, 3H, Ph), 6.45 (d, 1H, J = 16 Hz,
CH), 3.82 (s, 3H, CH3 ). 13 C NMR (100 MHz, ppm, CDCl3 ): δ = 175.3,
167.8, 143.2, 136.2, 135.1, 131.4, 127.8, 126.2, 119.2, 51.5. IR (KBr,
cm−1 ): ν 3034, 2940, 1718.
1
Methyl trans-4-formylcinnamate (entry 7, Table 4)
M.p. 82–84 ◦ C;[21] found 81–84 ◦ C. 1 H NMR (400 MHz, CDCl3 ):
δ = 10.10 (s, 1H, CHO), 7.92 (d, 2H, J = 8.4 Hz, Ph), 7.71 (d,
1H, J = 15.6 Hz, CH), 7.66 (d, 2H, J = 8.2 Hz, Ph), 6.57 (d, 1H,
J = 15.8 Hz, CH), 3.85 (s, 3H, CH3 ). 13 C NMR (100 MHz, ppm, CDCl3 ):
δ = 191.3, 168.8, 143.1, 140.0, 137.2, 130.2, 130.1, 128.3, 128.0,
121.0, 52.5. IR (KBr, cm−1 ): ν 3034, 2940, 2750, 1725, 1710.
General Procedure for the Microwave-assisted Heck
Cross-coupling Reaction
A suspension of aryl halide (2 mmol), olefin (5 mmol), K2 CO3
(2.2 mmol), palladacycle complex (0.1 mol%) and NMP (5 ml)
equipped with a magnetic stirring bar and a condenser for refluxing
was stirred under air atmosphere. In the case of microwave assisted
reactions, the mixture was heated under microwave oven at 130 ◦ C
and 600 W microwave irradiation. In the case of conventional
heating reactions, the above mixture was heated at 130 ◦ C in an oil
bath. The reaction progress was followed by TLC (hexane–EtOAc,
85 : 15, as eluent). After competition of the reaction, the mixture
was cooled to room temperature and was diluted with ether and
water. Then the organic layer was washed with brine, dried over
MgSO4 , filtered and evaporated under reduced pressure using
rotary evaporator to give the crude product that was purified by
recrystallization from ethanol.
trans-Stilbene (entry 2, Table 3 and entries 1, 2 and 11, Table 5)
Appl. Organometal. Chem. 2010, 24, 798–804
M.p. 58–60 ◦ C;[21] found 58–61 ◦ C 1 H NMR (500 MHz, CDCl3 ):
δ = 8.31 (d, 1H, J = 8.3 Hz, Ph), 7.97 (d, 1H, J = 15.8 Hz, CH),
7.88 (d, 1H, J = 8.2 Hz, Ph), 7.83 (d, 1H, J = 7.2 Hz, Ph), 7.69 (d,
2H, J = 7.4 Hz, Ph), 7.63–7.55 (m, 3H, Ph), 7.49 (t, 2H, J = 7.5 Hz,
Ph), 7.38 (t, 1H, J = 7.3 Hz, Ph), 7.24 (d, 1H, J = 16 Hz, CH). 13 C
NMR (100 MHz, ppm, CDCl3 ): δ = 136.7, 134.2, 133.9, 132.8, 130.7,
130.4, 130.1, 129.5, 128.7, 127.5, 126.4, 126.3, 126.1, 125.7, 125.6,
124.7, 123.8, 123.4. IR (KBr, cm−1 ): ν 3045, 1593.
trans-9-Styrylphenanthrene (entry 9, Table 5)
M.p. 104–108 ◦ C;[21] found 106–108 ◦ C 1 H NMR (400 MHz, CDCl3 ):
δ = 8.72 (d, 1H, J = 8 Hz, Ph), 8.72 (d, 1H, J = 8 Hz, Ph), 8.28 (d, 1H,
J = 8.8 Hz, Ph), 7.93 (s, 1H, Ph), 7.94 (d, 1H, J = 8.8 Hz, Ph), 7.90 (d,
1H, J = 16 Hz, CH), 7.74–7.61 (m, 6H, Ph), 7.41 (t, 2H, J = 7.6 Hz,
Ph), 7.34 (t, 1H, J = 7.6 Hz), 7.25 (d, 1H, J = 16 Hz, CH). 13 C NMR
(100 MHz, ppm, CDCl3 ): δ = 137.6, 134.0, 132.2, 131.9, 130.8, 130.5,
130.3, 128.8, 128.7, 128.3, 128.1, 127.1, 126.9, 126.8, 126.7, 126.6,
126.4, 124.7, 124.6, 123.2, 122.8, 122.6. IR (KBr, cm−1 ): ν 3045, 1593.
c 2010 John Wiley & Sons, Ltd.
Copyright wileyonlinelibrary.com/journal/aoc
803
M.p. 122–123 ◦ C;[27] found 121–122 ◦ C. 1 H NMR (500 MHz, CDCl3 ):
δ = 7.60 (d, 4H, J = 7.4 Hz, Ph), 7.45 (t, 4H, J = 7.6 Hz, Ph), 7.35
(t, 2H, J = 7.6 Hz, Ph), 7.22 (s, 2H, CH). 13 C NMR (100 MHz, ppm,
CDCl3 ) δ = 137.8 (2 C), 128.7 (4 C), 127.9 (4 C), 127.7 (2 C), 126.5
(2 C). IR (KBr, cm−1 ): ν 3076, 1594, 1493.
trans-1-Styrylnaphthalene (entry 8, Table 5)
A. R. Hajipour, K. Karami and G. Tavakoli
trans-4-Acetylstilbene (entry 6, Table 3 and entries 6 and 12, Table 5)
M.p. 140–144 ◦ C,[27] found 136–140 ◦ C.1 H NMR (500 MHz, CDCl3 ):
δ = 8.01 (d, 2H, J = 8.3 Hz), 7.64 (d, 2H, J = 8.3 Hz), 7.59 (d, 2H,
J = 7.5 Hz), 7.44 (t, 2H, J = 7.6 Hz), 7.35 (t, 1H, J = 7.1 Hz), 7.28
(d, 1H, J = 16.3 Hz), 7.19 (d, 1H, J = 16.3 Hz), 2.53 (s, 3H).13 C NMR
(100 MHz, ppm, CDCl3 ): δ = 197.5, 142.0, 136.7, 136.0, 131.5, 129.5,
129.1, 129.0, 128.8, 128.3, 128.2, 127.5, 127.4, 126.8, 126.5, 26.8. IR
(KBr, cm−1 ): ν 3019, 2960, 1678, 1600.
trans-3-Chlorostilbene (entry 5, Table 5)
M.p. 64–69 ◦ C;[21] found 65–69 ◦ C.1 H NMR (400 MHz, CDCl3 ): 7.51
(d, 1H, J = 7.2 Hz), 7.40–7.38 (m, 3H), 7.39–7.26 (m, 5H), 7.13 (d,
1H, J = 16.4 Hz), 7.11 (d, 1H, J = 16.4 Hz). 13 C NMR (100 MHz, ppm,
CDCl3 ): δ = 139.9, 136.6, 134.7, 130.3, 131.1, 129.1, 128.1, 128.0,
127.5, 127.5, 126.7, 126.6, 126.3, 124.8. IR (KBr, cm−1 ): ν 3045, 2950,
1589.
Methyl trans-4-cyanocinnamate (entry 4, Table 4)
M.p. 119–121 ◦ C;[21] found 118–121 ◦ C.1 H NMR (500 MHz, CDCl3 ):
δ = 7.69 (t, 2H, J = 8.4 Hz), 7.62 (d, 1H, J = 8 Hz), 7.58 (d, 1H,
J = 8.1 Hz), 7.28 (d, 1H, J = 16 Hz), 6.54 (d, 1H, J = 16 Hz), 3.88
(s, 3H). 13 C NMR (100 MHz, ppm, CDCl3 ): δ = 166.6, 142.4, 138.6,
132.7, 132.7, 128.4, 128.3, 121.4, 118.4, 113.4, 52.0. IR (KBr, cm−1 ):
ν 3044, 2956, 2225, 1720, 1639.
Acknowledgments
We gratefully acknowledge the funding support received for
this project from the Isfahan University of Technology, I. R. Iran
and Isfahan Science and Technology Town, I. R. Iran. Further
financial support from Center of Excellence in Sensor and Green
Chemistry Research (Isfahan University of Technology) is gratefully
acknowledged.
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using, microwave, complex, hecke, reaction, monomeric, couplings, palladated, benzoylmethylenetriphenylphosphorane, irradiation, ortho, methoxy
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