Synlett 2016; 27(16): 2333-2338
DOI: 10.1055/s-0035-1562607
letter
© Georg Thieme Verlag Stuttgart · New York

Graphene-Supported Palladium Complex: A Highly Efficient, Robust and Recyclable Catalyst for the Suzuki–Miyaura Cross-Coupling of Various Aryl Halides

Abu Taher
Department of Chemistry, Inha University, Incheon 402-751, Republic of Korea   Email: imlee@inha.ac.kr
,
Dong-Jin Lee
Department of Chemistry, Inha University, Incheon 402-751, Republic of Korea   Email: imlee@inha.ac.kr
,
Ik-Mo Lee*
Department of Chemistry, Inha University, Incheon 402-751, Republic of Korea   Email: imlee@inha.ac.kr
› Author Affiliations
Further Information

Publication History

Received: 02 June 2016

Accepted after revision: 30 June 2016

Publication Date:
28 July 2016 (online)


Abstract

We present a novel strategy based on the immobilization of a palladium complex on reduced graphene oxide for the development of a heterogeneous catalytic system with high efficiency and good recyclability. The prepared catalyst was tested for Suzuki–Miyaura cross-coupling reactions and shown to have a high catalytic efficiency, giving 83−98% conversion of the reactants under mild conditions. Moreover, it could be readily recycled and reused several times without significant loss of activity.

Supporting Information

 
  • References and Notes

  • 1 Wang S, Li J, Miao T, Wu W, Li Q, Zhuang Y, Zhou Z, Qiu L. Org. Lett. 2012; 14: 1966
  • 2 Shukla SP, Tiwari RK, Verma AK. J. Org. Chem. 2012; 77: 10382
  • 3 Keske EC, Zenkina OV, Wang R, Crudden CM. Organometallics 2012; 31: 6215
  • 4 Banwell MG, Goodwin TE, Ng S, Smith JA, Wong JD. Eur. J. Org. Chem. 2006; 3043
  • 5 Kotha S, Lahiri K. Eur. J. Org. Chem. 2007; 1221
  • 6 Lee D.-H, Jin M.-J. Org. Lett. 2011; 13: 252
  • 7 Cole-Hamilton DJ. Science 2003; 299: 1702
  • 8 Herrmann WA, Kohlpaintner CW. Angew. Chem. 1993; 105: 1588
    • 9a Taher A, Kim J.-B, Jung J.-Y, Ahn W.-S, Jin M.-J. Synlett 2009; 2477
    • 9b Wittmann S, Schätz A, Grass RN, Stark WJ, Reiser O. Angew. Chem. Int. Ed. 2010; 49: 1867
    • 10a Paul S, Clark JH. Green Chem. 2003; 5: 635
    • 10b Horniakova J, Raja T, Kubota Y, Sugi Y. J. Mol. Catal. A: Chem. 2004; 217: 73
  • 11 Uozumi Y. Bull. Chem. Soc. Jpn. 2008; 81: 1183
  • 12 Andrés R, de Jesús E, Flores JC. New J. Chem. 2007; 31: 1161
  • 13 Garcia-Bernabé A, Tzschucke CC, Bannwarth W, Haag R. Adv. Synth. Catal. 2005; 347: 1389
  • 14 Liu K, Chen T, Hou Z, Wang Y, Dai L. Catal. Lett. 2014; 144: 314
    • 15a Bai C, Zhao Q, Li Y, Zhang G, Zhang F, Fan X. Catal. Lett. 2014; 144: 1617
    • 15b Chua CK, Pumera M. Chem. Soc. Rev. 2014; 43: 291
  • 16 Meyer JC, Geim AK, Katsnelson MI, Novoselov KS, Booth TJ, Roth S. Nature 2007; 446: 60
  • 17 Dreyer DR, Park S, Bielawski CW, Ruoff RS. Chem. Soc. Rev. 2010; 39: 228
  • 18 Tan R, Li C, Luo J, Kong Y, Zheng W, Yin D. J. Catal. 2013; 298: 138
  • 19 Morimoto N, Yamamoto S-i, Takeuchi Y, Nishina Y. RSC. Adv. 2013; 3: 15608
  • 20 Santra S, Hota PK, Bhattacharyya R, Bera P, Ghosh P, Mandal SK. ACS. Catal. 2013; 3: 2776
  • 21 Shang N, Feng C, Zhang H, Gao S, Tang R, Wang C, Wang Z. Catal. Commun. 2013; 40: 111
  • 22 Liu M, Lu Y, Chen W. Adv. Funct. Mater. 2013; 23: 1289
  • 23 Qin Y, Li J, Kong Y, Li X, Tao Y, Li S, Wang Y. Nanoscale 2014; 6: 1281
  • 24 Qi J, Lv W, Zhang G, Li Y, Zhang G, Zhang F, Fan X. Nanoscale 2013; 5: 6275
  • 25 Feng C, Zhang H.-Y, Shang N.-Z, Gao S.-T, Wang C. Chin. Chem. Lett. 2013; 24: 539
  • 26 Nie Y, Hübert T. Polym. Int. 2011; 60: 1574
  • 27 Zhan Y, Wu J, Xia H, Yan N, Fei G, Yuan G. Macromol. Mater. Eng. 2011; 296: 590
  • 28 Huang K.-J, Niu D.-J, Liu X, Wu Z.-W, Fan Y, Chang Y.-F, Wu Y.-Y. Electrochim. Acta 2011; 56: 2947
  • 29 Pham VH, Cuong TV, Hur SH, Oh E, Kim EJ, Shin EW, Chung JS. J. Mater. Chem. 2011; 21: 3371
  • 30 Zhang X, Wan S, Pu J, Wang L, Liu X. J. Mater. Chem. 2011; 21: 12251
  • 31 Stankovich S, Dikin DA, Piner RD, Kohlhaas KA, Kleinhammes A, Jia Y, Wu Y, Nguyen ST, Ruoff RS. Carbon 2007; 45: 1558
  • 32 Wang H, Robinson JT, Li X, Dai H. J. Am. Chem. Soc. 2009; 131: 9910
  • 33 Tiberj A, Rubio-Roy M, Paillet M, Huntzinger J.-R, Landois P, Mikolasek M, Contreras S, Sauvajol J.-L, Dujardin E, Zahab A.-A. Sci. Rep. 2013; 3: 2355
  • 34 Parambhath VB, Nagar R, Sethupathi K, Ramaprabhu S. J. Phys. Chem. C 2011; 115-15679
  • 35 Fang M, Wang K, Lu H, Yang Y, Nutt S. J. Mater. Chem. 2009; 19: 7098
  • 36 Rakhi RB, Chen W, Cha D, Alshareef HN. J. Mater. Chem. 2011; 21: 16197
  • 37 Xue Y, Liu Y, Lu F, Qu J, Chen H, Dai L. J. Phys. Chem. Lett. 2012; 3: 1607
  • 38 Yang D, Velamakanni A, Bozoklu G, Park S, Stoller M, Piner RD, Stankovich S, Jung I, Field DA, Ventris CA. Jr, Ruoff RS. Carbon 2009; 47: 145
  • 39 Wang M, Zhao Y, Xu R, Zhang M, Fu RK. Y, Chu PK. Diamond Relat. Mater. 2013; 38: 28
  • 40 Siamaki AR, Lin Y, Woodberry K, Connell JW, Gupton BF. J. Mater. Chem. A 2013; 1: 12909
  • 41 Brun N, Hesemann P, Laurent G, Sanchez C, Birot M, Deleuze H, Backov R. New J. Chem. 2013; 37: 157
    • 42a Phan NT. S, Van Der Sluys M, Jones CW. Adv. Synth. Catal. 2006; 348: 609
    • 42b Molander GA, Canturk B. Angew. Chem. Int. Ed. 2009; 48: 9240
    • 42c Milde B, Schaarschmidt D, Rüffer T, Lang H. Dalton Trans. 2012; 41: 5377
    • 43a Lee D.-H, Jung J.-Y, Lee I.-M, Jin M.-J. Eur. J. Org. Chem. 2008; 356
    • 43b Taher A, Kim J.-B, Jung J.-Y, Ahn W.-S, Jin M.-J. Synlett 2009; 2477
    • 43c Zhang Q, Su H, Luo J, Wei Y. Catal. Sci. Technol. 2013; 3: 235
  • 44 Suzuki–Miyaura Reaction; General Procedure The appropriate aryl halide (1.0 mmol), PhB(OH)2 (1.2 mmol), K2CO3 (2.0 mmol), and catalyst 3 (0.2 mol%) were heated in 1:1 EtOH–H2O (3.5 mL). When the reaction was complete, the mixture was diluted with H2O and CH2Cl2. The organic layer was separated, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel. As all of the products are known, characterization was by comparison of their 1H and 13C NMR spectra with literature data.
  • 45 Sabater S, Mata JA, Peris E. ACS Catal. 2014; 4: 2038
  • 46 Movahed SK, Esmatpoursalmani R, Bazgir A. RSC Adv. 2014; 4: 14586