Suzuki–Miyaura reaction by heterogeneously supported Pd nanoparticles on thio-modified multi walled carbon nanotubes as efficient nanocatalyst

Polyhedron 162 (2019) 240–244

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Suzuki–Miyaura reaction by heterogeneously supported Pd nanoparticles on thio-modified multi walled carbon nanotubes as efficient nanocatalyst Hojat Veisi a,⇑, Ahmad Nikseresht a, Nasim Ahmadi a, Kaveh Khosravi b, Fatemeh Saeidifar a a b

Department of Chemistry, Payame Noor University, Tehran, Iran Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran

a r t i c l e

i n f o

Article history: Received 22 November 2018 Accepted 31 January 2019 Available online 14 February 2019 Keywords: Multi-walled carbon nanotubes Thiol Palladium Nanocatalyst Suzuki

a b s t r a c t The palladium (Pd) supported on thio-modified multi walled carbon nanotubes (MWCNTs/CC-SH/Pd) was utilized as a useful and reusable nanocatalyst in Suzuki–Miyaura coupling reactions. The catalyst was really efficient for the Suzuki–Miyaura reaction of aryl halides (Ar–I, Ar–Br, Ar–Cl) with phenylboronic acid and conversion was good in most cases. The aryl iodides and aryl bromides reactions take place at room temperature, while reaction of aryl chlorides occurs at temperature of 80 °C. The products yields ranged between70% and 96%. The catalyst indicated excellent constancy and could be recycled and reused up to four cycles with no considerable change in its catalytic behavior. Ó 2019 Elsevier Ltd. All rights reserved.

1. Introduction Over the last decade, modified carbon nanotubes (CNTs) have been greatly investigated in terms of separation, features and catalytic behavior. This subject has been attentive owing to the particular catalytic application comparing with homogenous complexes of CNTs. Besides metal nanoparticles, diverse transition metal complexes such as polymers and porphyrins have been used to functionalize CNTs [1–5]. Accordingly, CNTs can probably be utilized as an effective solid support for cross coupling reactions [6–10]. Reactions containing carbon-carbon bond-formation in the presence of a palladium catalyst play a key role in synthetic organic chemistry [11]. These kind of reactions have been improved as a general technique for synthesizing modified biphenyls with biological activity, which have extremely influenced on pharmaceuticals, and are key yields in drug discovery and agricultural compounds [12–16]. Though, cross-coupling reactions are usually performed under homogeneous conditions, in which a ligand is used to enhance the performance and specificity of the catalyst, problems remain regarding the lack of recoverability and possible contamination owing to remaining metal by-products [17,18]. Although, several promising solutions have been obtain-

⇑ Corresponding author. E-mail address: [email protected] (H. Veisi). https://doi.org/10.1016/j.poly.2019.01.070 0277-5387/Ó 2019 Elsevier Ltd. All rights reserved.

able for solving this issue, this remains a concern for pharmacological uses. Solid-supported metal nanocatalysts have been used as optimal catalysts that maximize the reactivity and stability of the compounds and increase the efficiency of separation and recoverability level in more reactions. Therefore, many efforts have been recently carried out to improve novel metal nanocatalysts for such cross-coupling reactions in which the metal is immobilized on a group of compact supports such as activated carbon [19,20], zeolites [21,22], polymers [23,24], mesoporous silica [25,26], inorganic oxides [27,28], or nanoparticles [5,29–32]. CNTs owing to their thermal stability, large specific surface area, and good structural and electronic features are used as support systems for immobilization of the metal nanoparticles. Though, heterogeneous supports are chosen as they can be recycled efficiently, stabilized catalysts tend to experience a decrease in their activity [33,34]. Consequently, further investigations are required to develop heterogeneous Pd nanocatalysts with high activity, constancy and recoverability for the future of chemical and pharmacological industries. We previously immobilized palladium nanoparticles on thio modified-multi walled carbon nanotubes (MWCNTs/CC-SH/Pd) as heterogeneous and reusable nanocatalyst for Buchwald–Hartwig CAN cross coupling reactions [35]. Following our interest on the synthetic application of metal supported nanocatalysts [36], we tried to utilize MWCNTs/CC-SH/Pd as a catalyst in Suzuki–Miyaura coupling reaction under mild conditions.

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2. Experimental 2.1. Preparation of the MWCNTs/CC-SH/Pd The MWCNTs/CC-SH nanocatalyst is synthesized according to our earlier report [35]. Briefly, MWCNTs-COOH (1 g) was added to 50 mL of ethylenediamine (EDA) and stirring for 5 min. Next, (dicyclohexylcarbodiimide) DCC was poured into the solution and refluxed for 48 h. Finally, the synthesized MWCNTS-EDA was isolated trough centrifugation, rinsed with ethanol and dried in an oven at temperature of 80 °C for 8 h. Next phase, 100 mL of anhydrous THF, 0.5 g of MWCNTs-EDA and 0.2 ml of diisopropylethylamine (DIPEA) were poured into a 250 mL of round-bottom flask. Then, 0.23 g (1.5 mmol) of cyanoric chloride (CC) was added in temperature of 0 °C. Following 3 h of agitation, the solution was decanted and rinsed with 2  25 of fresh THF and next decanted. Then, acetonitrile (100 ml) and diisopropylethylamine (0.5 ml) were added to residue. 0.31 g of 2-mercaptoethanol (4 mmol) was poured into the mixture and agitated for 3 hours in ambient temperature and refluxed for 12 hours. At the end of the reaction, the solid products were filtered, rinsed with deionized water and next acetone and dried at temperature of 50 °C for 12 h. The clung 2-mercaptoethanol on triazine modified MWCNTs (MWCNTs/CC-SH) was achieved via this simple process. 500 mg of MWCNTs/CC-SH was dispersed in CH3CN (100 mL) in an ultrasonic bath for 30 min. Then, a yellow solution of PdCl2

SH

O

Pd

N N

O

HN O

O

N N

N

HN

Pd

HS

SH

HS

Pd

Pd

O N

NH NH O

O

Pd

HN

N H

R + X X = I, Br, Cl

O

R

B(OH)2 MWCNTs/CC-SH/Pd K2CO3, H2O-EtOH

Scheme 1. Synthesis of biaryls through the Suzuki cross-coupling reaction.

(30 mg) in 30 mL acetonitrile was poured into dispersion of MWCNTs/CC-SH and the resulted mixture was agitated for 10 h at temperature of 25 °C. Next, the MWCNTs/CC-SH/Pd(II) was isolated through centrifugation and rinsed with CH3CN, H2O and acetone respectively to eliminate the unreacted substrates. The MWCNTs/CC-SH/Pd(II) was reduced by hydrazine hydrate as following: MWCNTs/CC-SH/Pd(II) (50 mg) was dispersed in of water (60 mL), and next 100 lL of hydrazine hydrate (80%) was added. The pH of the mixture was set at 10 using 25% ammonium hydroxide and the reaction was performed at temperature of 95 °C for 2 h. The final product MWCNTs/CC-SH/Pd(0) was rinsed with water and dried in a vacuum at temperature of 40 °C. 2.2. General procedure for the Suzuki–Miyaura reaction 1 mmol of Aryl halide, 1.1 mmol of phenylboronic acid, 2 mmol of K2CO3, 10 mg of catalyst (contained 0.2 mol% Pd) and 2 mL of water/ethanol (1:1) were poured into a 5 mL flask, and mixed using a magnetic stirrer at RT or temperature of 80 °C (depending on the aryl halide). The development of the reactions was controlled using

Table 2 Scope of the Suzuki–Miyaura reaction.a Entry

RC6H4X

X

Time (h)

Yield (%)b

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

H H H 4-CH3 4-CH3 4-CH3 4-COCH3 4-COCH3 4-COCH3 4-CH3O 4-CH3O 4-NH2 4-NH2 4-OH 4-OH 2-Thienyl 2-Thienyl

I Br Cl I Br Cl I Br Cl I Br I Br I Br I Br

1.0 2.0 24 1.0 2.5 24 1.5 4.0 24 1.5 4.0 2.0 3.0 3.0 6.0 3.5 5.0

96 96 70c 96 96 65c 96 96 70c 96 92 90 85 96 90 95 90

a Reactions were carried out under aerobic conditions in 3 mL of H2O/EtOH (1:1), 1.0 mmol arylhalide,1.0 mmol phenylboronic acid and 2 mmol K2CO3 in the presence of catalyst (0.010 g, 0.2 mol% Pd) at room temperature. b Isolated yield. c At 80 °C.

Table 1 The optimization of reaction parameters for the Suzuki reaction of 4-bromotoluene with phenyl boronic acid.a

Br

B(OH) 2

various conditions

CH3

+

H3C

a b c

Entry

Pd (mol%)

Solvent

Base

Time (h)

Yield (%)b

1 2 3 4 5 6 7 8 9 10 11

0.2 0.2 0.2 0.2 0.2 0.2 0.1 0.2 0.3 0.2 0.0

DMF Toluene EtOH H2O EtOH/H2Oc EtOH/H2Oc EtOH/H2Oc EtOH/H2Oc EtOH/H2Oc EtOH/H2Oc EtOH/H2Oc

K2CO3 K2CO3 K2CO3 K2CO3 NaOAc Et3N K2CO3 K2CO3 K2CO3 No base K2CO3

3 3 3 5 3 4 2 1 1 12 12

65 50 75 45 75 65 80 98 96 Trace 0.0

Reaction conditions: 4-bromotoluene (1.0 mmol), phenylboronic acid (1.0 mmol), catalyst, base (2 mmol) and solvent (3 mL) at room temperature. Isolated yield. 3 mL (1:1).

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TLC. At the end of the reaction, the reaction mixture was centrifuged to separate the catalyst and ethyl acetate was used to extract the crude product. The pure products were achieved using column chromatography on silica with the hexane and ethyl acetate as eluent. 2.3. Procedure for reusing the catalyst After completion of the reaction, 5 mL of ethyl acetate was poured into the mixture and agitated for 5 min. Then, the catalyst

was isolated through centrifugation. In the following phase, the recovered catalyst was rinsed using EtOH and dried under vacuum. Next, the recovered catalyst was utilized for another cycle. 3. Results and discussion The Suzuki–Miyaura reaction, which is a CAC bond formation reaction of aryl halides with phenyl boronic acid, was used to Ar1 X Reductive elimination

Oxidative addition

MWCNTs Ar1 Ar2 Ar2 Ar1 Ar1

Ar2

Suzuki Reaction

X Ar1

X

Ar1

Transmetalation XB(OH)2 K2CO3

Fig. 1. Recyclability of catalyst in the Suzuki–Miyaura reaction.

Ar2 B(OH)2 K2CO3

Scheme 2. Possible mechanism of Suzuki reaction catalyzed by MWCNTs/CC-SH/ Pd.

Fig. 2. (a) SEM, (b) TEM and EDS data for reused catalyst after the 3 runs.

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H. Veisi et al. / Polyhedron 162 (2019) 240–244 Table 3 Catalytic performance of different catalysts in the coupling reaction of iodobenzene and bromobenzene with phenylbronic acid.

a b

1 a

) (TON)b

Entry

Catalyst (mol%)

Conditions

X

Time (h)

Yield (%)

TOF (h

1

Bis(oxamato)palladate(II) complex (5)

Et3N, n-Bu4NBr, 120 °C

2

NHC-Pd(II) complex (0.2)

K3PO4.3H2O, H2O, TBAB, 40 °C

3

SiO2-pA-Cyan-Cys-Pd (0.5)

K2CO3, H2O, 100 °C

4 5 6

Pd3(dba) (1) Pd–BOX (2) c-Fe2O3-acetamidine-Pd (0.12)

K3PO4, THF, 80 °C K2CO3, DMF, 70 °C Et3N, DMF, 100 °C

7

Pd-isatin Schiff base-c-Fe2O3 (0.5, 1.5)

Et3N, Solvent-free, 100 °C

8

MWCNTs/CC-SH/Pd (0.2)

K2CO3, H2O/EtOH, r.t.

I Br I Br I Br Br I I Br I Br I Br

2.0 2.0 5.0 6.0 5.0 5.5 24 6.0 0.5 0.5 0.5 0.7 1.0 2.0

78 65 98 90 95 88 77.7 100 96 96 95 90 96 96

7.8 (15.6) 6.5 (13) 98 (490) 75 (450) 38 (190) 32 (176) 3.24 (77.7) 8.3 (50) 1600 (800) 1600 (800) 380 (190) 85.7 (60) 480 (480) 240 (480)

Refs. [38] [39] [40] [41] [42] [43] [44] This work

TOF, turnover frequencies. TON, turnover number, moles of aryl halides converted per mole of Pd.

assess the MWCNTs/CC-SH/Pd heterogeneous nanocatalyst [36] (Scheme 1). Firstly, 4-bromotoluene and phenyl boronic acid at room temperature were utilized to carry out the Suzuki coupling reaction as a model for the further development in other reaction factors containing the solvent, base and the concentration of catalyst utilized. Table 1 presents the list of research performed on optimization of conditions. As expected, no target product was produced with no use of the catalyst, while, the yield and formation of the target product was quickly increased via addition of the catalyst to the mixture. A 1:1 ratio of H2O/EtOH solvent was applied in the reaction, and K2CO3 was the most effective bases amongst tested ones. The effectiveness of catalysts was assessed using diverse amounts of the catalyst ranging between 0.1 and 0.3 mol%, with 0.010 g (0.2 mol%) of the catalyst resulting in the highest yield. However, subject to the optimum conditions for reaction and in the presence of a catalyst, the reactions of structurally diverse aryl iodides, bromides and chlorides with phenylboronic acid were studied (Table 2). The outcomes clarify that aryl iodides and aryl bromides containing electron-donating and electron withdrawing parts with phenylboronic acid fittingly progressed and the equivalent coupling products was produced in plentiful (good to excellent) efficacies (Table 1, entries 4, 5, 7, 8, 10–15). Furthermore, the reactions between the unsubstituted iodobenzene and bromobenzene improve optimally and result in the associated products (Table 1, entries 1, 2). The reaction of 2-iodothiphene and 2bromothiophene as heterocyclic aryl halides combining with phenylboronic acid resulted in the coupling product by 95% and 90%, respectively (Table 2, entries 16 and 17). Substituted aryl chlorides are more economical comparing with aryl iodides and bromides, and more accessible for Pd-catalyzed cross-coupling reactions. Despite this, the aryl chlorides reactions subject to optimal reaction conditions at room temperature were properly lethargic; and so, the reaction temperature was increased to 80 °C. According to these conditions, the Suzuki–Miyaura reaction was optimal, and the predicted cross-coupling products were attained effectively (good to excellent performance) (Table 1, entries 3, 6, 9). It was found that the MWCNTs/CC-SH/Pd catalyst could be isolated easily through centrifugation and could be reused at least 3 cycles with the performances of 96%, 96%, 95% and 90% for the Suzuki coupling reaction between phenylboronic acid and 4-bromotoluene subject to K2CO3 (Fig. 1). At the end of the reaction, the catalyst was separated via centrifugation of the reaction mixture and rinsed several times by deionized water and ethanol. Next, it was dried in an oven at temperature of 50 °C and the recycled catalyst was stored to utilize in following reactions. ICP was utilized to assess, the leaching of Pd into the reaction solution following 3 runs that was achieved 1.58% and showed

the stability of the catalysts under the reaction. The SEM (scanning electron microscope), EDS (energy-dispersive X-ray spectroscopy) and TEM (transmission electron microscopy) analysis (Fig. 2) corresponding to the catalyst following the 3 runs indicated that the nanostructure of the catalyst was well-maintained. Based on the TEM image resulted from recycled catalyst, the Pd NPs were still well dispersed and Pd NPs were not accumulated. The heterogeneity of catalyst was measured via a hot filtration test performed for the Suzuki reaction between 4-bromotoluene and phenylboronic acid with MWCNTs/CC-SH/Pd under the same conditions. The performance of reaction was 70% following proceeding for 60 min, and then, the catalyst was separated to reuse. The reaction was continued for another 1 h following separating the catalyst and no increase was found in the product yield that shows the heterogeneity of the catalyst. Based on these outcomes and literature [37], a reaction mechanism was suggested for Suzuki coupling with the synthesized nanocatalyst (Scheme 2). The MWCNTs/CC-SH/Pd was compared with numerous previously reported Pd catalysts in terms of catalytic behavior in the Suzuki coupling reaction (Table 3). Based on the outcomes of this comparison in Table 3, the catalyst offered in current research shows more adaptations and performance competing with other offered systems. Furthermore, in the current method, the relevant products were obtained completely with excellent turnover frequencies (TOF) in milder conditions (for entry 6, the reaction conditions are hard). 4. Conclusions In current research, we have introduced a novel, effective procedure using MWCNTs/CC-SH/Pd as heterogeneous and recoverable nanocatalyst for the Suzuki–Miyaura cross-coupling reactions. This catalyst can be easily recycled without significant decrease in its catalytic performance and the suggested procedure can be a substitute technique for synthesis of biphenyl compounds. Acknowledgements We are thankful to Payame Noor University and Arak University for partial support of this work. References [1] H.X. Wu, R. Tong, X.Q. Qiu, H.F. Yang, Y.H. Lin, R.F. Cai, S.X. Qian, Carbon 45 (2007) 152. [2] J.L. Chen, K.H. Hsieh, Electrophoresis 31 (2010) 3937. [3] J. Jin, Z. Dong, J. He, R. Li, J. Ma, Nanoscale Res. Lett. 4 (2009) 578. [4] J. Guerra, M.A. Herrero, Nanoscale 2 (2010) 1390. [5] S. Santra, P. Ranjan, P. Bera, P. Ghosh, S.K. Mandal, RSC Adv. 2 (2012) 7523.

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