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Entangled Cu Complex Over Fe3O4@SiO2 as Supported Catalyst for Synthesis of Alkenyl Nitriles with Aromatic Aldehydes and Acetonitrile

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Abstract

An efficient, green and practical approach to synthesize alkenyl nitriles using new supported Cu(II) catalyst via aromatic aldehydes and acetonitrile was developed. The novel catalyst was characterized by FT-IR, XRD, SEM/EDX, TEM, TGA and VSM. Interestingly, the catalyst was found to be active for synthesis of alkenyl nitriles, which were readily obtained in good yields under mild conditions. But most importantly, the original catalyst could be conveniently recovered and recycled from the reaction system by applying an external magnet and reused in four cycles without significant loss in catalytic activity.

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References

  1. Miller JS, Manson JL (2001) Acc Chem Res 34:563

    Article  CAS  Google Scholar 

  2. Fleming FF, Wang Q (2003) Chem Rev 103:2035

    Article  CAS  Google Scholar 

  3. Qin C, Jiao N (2010) J Am Chem Soc 132:15893

    Article  CAS  Google Scholar 

  4. Zhou W, Xu JJ, Zhang LR, Jiao N (2010) Org Lett 12:2888

    Article  CAS  Google Scholar 

  5. Pradal A, Evano G (2014) Chem Commun 50:11907

    Article  CAS  Google Scholar 

  6. Huang XQ, Jiao N (2014) Org Biomol Chem 12:4324

    Article  CAS  Google Scholar 

  7. Powell KJ, Han LC, Sharma P, Moses JE (2014) Org Lett 16:2158

    Article  CAS  Google Scholar 

  8. Cheng YN, Duan Z, Yu LJ, Li ZX, Zhu Y, Wu YJ (2008) Org Lett 10:901

    Article  CAS  Google Scholar 

  9. Wang R, Falck JR (2013) Chem Commun 49:6516

    Article  CAS  Google Scholar 

  10. Murray RW (2008) Chem Rev 108:2688

    Article  CAS  Google Scholar 

  11. Crooks RM, Zhao MQ, Sun L, Chechik V, Yeung LK (2001) Acc Chem Res 34:181

    Article  CAS  Google Scholar 

  12. Perelaer J, Smith PJ, Mager D, Soltman D, Volkman SK, Subramanian V, Korvink JG, Schubert US (2010) J Mater Chem 20:8446

    Article  CAS  Google Scholar 

  13. Zarnegar Z, Safari J (2014) New J Chem 38:4555

    Article  CAS  Google Scholar 

  14. Huang CC, Lo SL, Tsai SM, Lien HL (2011) J Environ Monit 13:2406

    Article  CAS  Google Scholar 

  15. Li HQ, Li CP, Bai J, Zhang CL, Sun WY (2014) RSC Adv 4:48362

    Article  CAS  Google Scholar 

  16. He DP, Zeng C, Xu C, Cheng NC, Li HG, Mu SC, Pan M (2011) Langmuir 27:5582

    Article  CAS  Google Scholar 

  17. Bian XJ, Lu XF, Jin E, Kong LR, Zhang WJ, Wang C (2010) Talanta 81:813

    Article  CAS  Google Scholar 

  18. Kim M, Park JC, Kim A, Park KH, Song H (2012) Langmuir 28:6441

    Article  CAS  Google Scholar 

  19. Ogasawara S, Kato S (2010) J Am Chem Soc 132:4608

    Article  CAS  Google Scholar 

  20. Crudden CM, Sateesh M, Lewis R (2005) J Am Chem Soc 127:10045

    Article  CAS  Google Scholar 

  21. Ji Y, Jain S, Davis RJ (2005) J Phys Chem B 109:17232

    Article  CAS  Google Scholar 

  22. Zhu MY, Wang Y, Wang CJ, Li W, Diao GW (2013) Catal Sci Technol 3:952

    Article  CAS  Google Scholar 

  23. Wang HQ, Wei X, Wang KX, Chen JS (2012) Dalton Trans 41:3204

    Article  CAS  Google Scholar 

  24. Wang HF, Ariga H, Dowler R, Sterrer M, Freund HJ (2012) J Catal 286:1

    Article  CAS  Google Scholar 

  25. Ludwig W, Savara A, Brandt B, Schauermann S (2011) Phys Chem Chem Phys 13:966

    Article  CAS  Google Scholar 

  26. Shylesh S, Schünemann V, Thiel WR (2010) Angew Chem Int Ed 49:3428

    Article  CAS  Google Scholar 

  27. Laska U, Frost CG, Price GJ, Plucinski PK (2009) J Catal 268:318

    Article  CAS  Google Scholar 

  28. Dong B, Miller DL, Li CY (2012) J Phys Chem Lett 3:1346

    Article  CAS  Google Scholar 

  29. Jeong U, Teng XW, Wang Y, Yang H, Xia YN (2007) Adv Mater 19:33

    Article  CAS  Google Scholar 

  30. Lu AH, Salabas EL, Schuth F (2007) Angew Chem Int Ed 46:1222

    Article  CAS  Google Scholar 

  31. Laurent S, Forge D, Port M, Roch A, Robic C, Elst LV, Muller RN (2008) Chem Rev 108:2064

    Article  CAS  Google Scholar 

  32. Zou J, Peng YG, Tang YY (2014) RSC Adv 4:9693

    Article  CAS  Google Scholar 

  33. Polshettiwar V, Molnar A (2007) Tetrahedron 63:6949

    Article  CAS  Google Scholar 

  34. Polshettiwar V, Len C, Fihri A (2009) Coord Chem Rev 253:2599

    Article  CAS  Google Scholar 

  35. Wang P, Liu HZ, Niu JR, Li R, Ma JT (2014) Catal Sci Technol 4:1333

    Article  CAS  Google Scholar 

  36. Cho JK, Najman R, Dean TW, Ichihara OI, Muller C, Bradley M (2006) J Am Chem Soc 128:6276

    Article  CAS  Google Scholar 

  37. Mishra GS, Kumar A (2011) Catal Sci Technol 1:1224

    Article  CAS  Google Scholar 

  38. Tomioka T, Takahashi Y, Vaughan TG, Yanase T (2010) Org Lett 12:2171

    Article  CAS  Google Scholar 

  39. Mohammad AA, Ali RA (2014) Catal Sci Technol 4:1151

    Article  Google Scholar 

  40. Lien YH, Wu TM (2008) J Colloid Interface Sci 326:517

    Article  CAS  Google Scholar 

  41. Jarrais B, Pereira C, Silva AR, Carvalho AP, Pires J, Freire C (2009) Polyhedron 28:994

    Article  CAS  Google Scholar 

  42. Zheng J, Dong Y, Wang W, Ma Y, Hu J, Chen X (2013) Nanoscale 5:4894

    Article  CAS  Google Scholar 

  43. Feng B, Hong RY, Wang LS, Guo L, Li HZ, Ding J, Zheng Y, Wei DG (2008) Colloids Surf A 328:52

    Article  CAS  Google Scholar 

  44. Sun J, Yu GL, Liu LL, Li ZF, Kan QB, Huo QS, Guan JQ (2014) Catal Sci Technol 4:1246

    Article  CAS  Google Scholar 

  45. Zhang L, Li PH, Li HJ, Wang L (2012) Catal Sci Technol 2:1859

    Article  CAS  Google Scholar 

  46. Wang X, Dou PP, Zhao P, Zhao CM, Ding Y, Xu P (2009) ChemSusChem 2:947

    Article  CAS  Google Scholar 

  47. Zhang Q, Su H, Luo J, Wei YY (2012) Green Chem 14:201

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (21402066), the Natural Science Foundation of Jiangsu Province, China (BK2012547), (BK2012547) and (BK20140139), MOE & SAFEA for the 111 Project (B13025) for financial support.

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Correspondence to Haijun Wang or Wei Li.

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Gu, Z., Wang, Y., Yao, Y. et al. Entangled Cu Complex Over Fe3O4@SiO2 as Supported Catalyst for Synthesis of Alkenyl Nitriles with Aromatic Aldehydes and Acetonitrile. Catal Lett 145, 2046–2054 (2015). https://doi.org/10.1007/s10562-015-1602-8

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  • DOI: https://doi.org/10.1007/s10562-015-1602-8

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