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CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions

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Abstract

In this paper, we report the synthesis of Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst.

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References

  1. Negwar M (1994) Organic-chemical drugs and their synonyms. Akademie Verlag/VCH Publishers, New York

    Google Scholar 

  2. Corbet JP, Mignani G (2006) Chem Rev 106:2651

    CAS  PubMed  Google Scholar 

  3. Ritleng V, Sirlin C, Pfeffer M (2002) Chem Rev 102:1731

    CAS  PubMed  Google Scholar 

  4. Muci AR, Buchwals SL (2002) Top Curr Chem 219:131

    CAS  Google Scholar 

  5. Diederich F, de Meijere A (2004) Metal-catalyzed cross-coupling reactions. Wiley-VCH, Weinheim

    Google Scholar 

  6. Campeau LC, Fagnou K (2006) Chem Commun. https://doi.org/10.1039/B515481M

    Article  Google Scholar 

  7. Daugulis O, Zaitsev VG, Shabashou D, Pham QN, Lazareva A (2006) Synlett 20:3382

    Google Scholar 

  8. Godula K, Sames S (2006) Science 312:67

    CAS  PubMed  Google Scholar 

  9. Dick AR, Sanford MS (2006) Tetrahedron 62:2439

    CAS  Google Scholar 

  10. Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174

    CAS  PubMed  Google Scholar 

  11. Seregin IV, Gevorgyan V (2007) Chem Soc Rev 36:1173

    CAS  PubMed  PubMed Central  Google Scholar 

  12. Davies HML, Manning JR (2008) Nature 451:417

    CAS  PubMed  PubMed Central  Google Scholar 

  13. Monnier F, Taillefer M (2009) Angew Chem Int Ed 48:6954

    CAS  Google Scholar 

  14. Evano G, Blanchard N, Toumi M (2008) Chem Rev 108:3054

    CAS  PubMed  Google Scholar 

  15. Sambiagio C, Marsden SP, Blacker AJ, McGowan PC (2014) Chem Soc Rev 43:3525

    CAS  PubMed  Google Scholar 

  16. Lindley J (1984) Tetrahedron 40:1433

    CAS  Google Scholar 

  17. Ley SV, Thomas AW (2003) Angew Chem Int Ed 42:5400

    CAS  Google Scholar 

  18. Ley SV, Thomas AW (2003) Angew Chem 115:5558

    Google Scholar 

  19. Sawyer JS (2000) Tetrahedron 56:5045

    Google Scholar 

  20. Frlan R, Kikelj D (2006) Synthesis 14:2271

    Google Scholar 

  21. Zhang H, Ruiz-Castillo P, Buchwald SL (2018) Org Lett 20:1580

    CAS  PubMed  PubMed Central  Google Scholar 

  22. MacQueen PM, Tassone JP, Diaz C, Stradiotto M (2018) J Am Chem Soc 140:5023

    CAS  PubMed  Google Scholar 

  23. Sun H, Sun Y, Tian X, Zhao Y, Qi X (2013) Asian J Chem 25:6189

    CAS  Google Scholar 

  24. Singh AS, Shendage SS, Nagarkar JM (2013) Tetrahedron Lett 54:6319

    CAS  Google Scholar 

  25. Singh AS, Shendage SS, Nagarkar JM (2014) Tetrahedron Lett 55:4917

    CAS  Google Scholar 

  26. Miaoa T, Wang L (2007) Tetrahedron Lett 48:95

    Google Scholar 

  27. Baghbanian SM, Yadollahy H, Tajbakhsh M, Farhangb M, Biparva P (2014) RSC Adv 4:62532

    CAS  Google Scholar 

  28. Mullick K, Biswas S, Kim C, Ramprasad R, Angeles-Boza AM, Suib SL (2017) Inorg Chem 56:10290

    CAS  PubMed  Google Scholar 

  29. Saha P, Ashif Ali M, Ghosh P, Punniyamurthy T (2010) Org Biomol Chem 8:5692

    CAS  PubMed  Google Scholar 

  30. Yang L, Jin Y, Fang X, Cheng Z, Zhou Z (2017) Ind Eng Chem Res 56:14182

    CAS  Google Scholar 

  31. Zhao L, Zheng K, Tong J, Jin J, Shen C (2019) Catal Lett 149:2607

    CAS  Google Scholar 

  32. Fang Q, Cheng Q, Xu H, Xuan S (2014) Dalton Trans 43:2588

    CAS  PubMed  Google Scholar 

  33. Nicholas KM (1987) Acc Chem Res 20:207

    CAS  Google Scholar 

  34. Mohammadinezhad A, Akhlaghinia B (2017) Green Chem 19:5625

    CAS  Google Scholar 

  35. Jahanshahi R, Akhlaghinia B (2017) Catal Lett 147:2640

    CAS  Google Scholar 

  36. Razavi N, Akhlaghinia B, Jahanshahi R (2017) Catal Lett 147:360

    CAS  Google Scholar 

  37. Zarghani M, Akhlaghinia B (2016) Bull Chem Soc Jpn 89:1192

    CAS  Google Scholar 

  38. Ghasemzadeh MS, Akhlaghinia B (2019) Aust J Chem 72:674

    CAS  Google Scholar 

  39. Cheng X, Zhang A, Hou K, Liu M, Wang Y, Song C, Zhang G, Guo X (2013) Dalton Trans 42:13698

    CAS  PubMed  Google Scholar 

  40. Alqadami AA, Naushad Mu, Alothman ZA, Ghfar AA (2017) ACS Appl Mater Interfaces 9:36026

  41. Yaghi OM, O’Keeffe M, Ockwig NW, Chae HK, Eddaoudi M, Kim J (2003) Nature 423:705

    CAS  PubMed  Google Scholar 

  42. Jin M, Mou ZL, Zhang RL, Liang SS, Zhang ZQ (2017) Biosens Bioelectron 91:162

    CAS  PubMed  Google Scholar 

  43. Cohen SM (2012) Chem Rev 112:970

    CAS  PubMed  Google Scholar 

  44. Stock N, Biswas S (2012) Chem Rev 112:933

    CAS  PubMed  Google Scholar 

  45. Kitaura R, Kitagawa S, Kubota Y, Kobayashi TC, Kindo K, Mita Y, Matsuo A, Kobayashi M, Chang HC, Ozawa TC, Suzuki M, Sakata M, Takata M (2002) Science 298:2358

    CAS  PubMed  Google Scholar 

  46. Ferey G, Cheetham AK (1999) Science 283:1125

    CAS  Google Scholar 

  47. Lu G, Li S, Guo Z, Farha OK, Hauser BG, Qi X, Wang Y, Wang X, Han S, Liu X, DuChene JS, Zhang H, Zhang Q, Chen X, Ma J, Loo SCJ, Wei WD, Yang Y, Hupp J, Huo F (2012) Nat Chem 4:310

    CAS  PubMed  Google Scholar 

  48. Cadiau A, Adil K, Bhatt PM, Belmabkhout Y, Eddaoudi M (2016) Science 353:137

    CAS  PubMed  Google Scholar 

  49. Cui X, Chen K, Xing H, Yang Q, Krishna R, Bao Z, Wu H, Zhou W, Dong X, Han Y, Li B, Ren Q, Zaworotko MJ, Chen B (2016) Science 353:141

    CAS  PubMed  Google Scholar 

  50. Gascon J, Aktay U, Hernandez-Alonso MD, van Klink GPM, Kapteijn F (2009) J Catal 261:75

    CAS  Google Scholar 

  51. Ahnfeldt T, Gunzelmann D, Loiseau T, Hirsemann D, Senker J, Fé rey G, Stock N (2009) Inorg Chem 48:3057

  52. Naushad M, Ahamad T, Al-Maswari BM, Alqadami AA, Alshehri SM (2017) Chem Eng J 330:1351

    CAS  Google Scholar 

  53. Buckingham D, Jones D (1965) Inorg Chem 4:1387

    CAS  Google Scholar 

  54. Mahmoud ME, Abdelwahab MS, Fathallah EM (2013) Chem Eng J 223:318

    CAS  Google Scholar 

  55. Liu J, Zou X, Liu C, Cai K, Zhao N, Zheng W, Zhu G (2016) CrystEngComm 18:525

    CAS  Google Scholar 

  56. Yang Y, Wang W, Li H, Jin X, Wang H, Zhang L, Zhang Y (2017) Mater Lett 197:17

    CAS  Google Scholar 

  57. Alqadami AA, Ali Khan M, Siddiqui MR, Abdullah Alothman Z (2018) Microporous Mesoporous Mater 261:198

    Google Scholar 

  58. Mubashir M, Fong YY, Keong LK (2018) Sep Purif Technol 199:140

    CAS  Google Scholar 

  59. Rostamnia S, Jafari M (2017) Appl Organomet Chem 31:3584

    Google Scholar 

  60. Mizuno J (1960) J Phys Soc Jpn 15:1412

    CAS  Google Scholar 

  61. Chen XY, Vinh-Thang H, Rodrigue D, Kaliaguine S (2012) Ind Eng Chem Res 51:6895

    CAS  Google Scholar 

  62. Abedini R, Omidkhah M, Dorosti F (2014) RSC Adv 4:36522

    CAS  Google Scholar 

  63. Bromberg L, Su X, Hatton TA (2013) ACS Appl Mater Interfaces 5:5468

    CAS  PubMed  Google Scholar 

  64. Feijani EA, Tavasoli A, Mahdavi H (2015) Ind Eng Chem Res 54:12124

    Google Scholar 

  65. Liu L, Tai X, Zhou X, Liu L (2017) CRCU 33:231

    CAS  Google Scholar 

  66. Chen XY, Hoang VT, Rodrigue D, Kaliaguine S (2013) RSC Adv 3:24266

    CAS  Google Scholar 

  67. Hashemzadeh A, Amini MM, Tayebee R, Sadeghian A, Durndell LJ, Isaacs MA, Osatiashtiani A, Parlett CMA, Lee AF (2017) Mol Catal 440:96

    CAS  Google Scholar 

  68. Carrara C, Irusta S, Lombardo E, Cornaglia L (2001) Appl Catal A 217:275

    CAS  Google Scholar 

  69. Chen Y, Zhao S, Liu Z (2015) Phys Chem Chem Phys 17:14012

    CAS  PubMed  Google Scholar 

  70. Yong-Hao Tan B, Yong-Chua T (2015) Synlett 26:1697

    Google Scholar 

  71. Wong YC, Jayanth TT, Cheng CH (2006) Org Lett 8:5613

    CAS  PubMed  Google Scholar 

  72. Ibrahim H, Dabai Bala M (2015) J Organomet Chem 794:301

    CAS  Google Scholar 

  73. Ghorbani-Vaghei R, Hemmati S, Veisi H (2013) Tetrahedron Lett 54:7095

    CAS  Google Scholar 

  74. Zhang P, Yuan J, Li H, Liu X, Xu X, Antonietti M, Wang Y (2013) RSC Adv 3:1890

    CAS  Google Scholar 

  75. Zolfigol MA, Khakyzadeh V, Moosavi-Zare AR, Rostami A, Zare A, Iranpoor N, Beyzavi MH, Luque R (2013) Green Chem 15:2132

    CAS  Google Scholar 

  76. Arundhathi R, Sreedhar B, Parthasarathy G (2011) Appl Clay Sci 51:131

    CAS  Google Scholar 

  77. Sharma RK, Gaur R, Yadav M, Rathi AK, Pechousek J, Petr M, Zboril R, Gawande MB (2015) Chem Cat Chem 7:3495

    CAS  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge the partial support of this study by Ferdowsi University of Mashhad Research Council (Grant no. p/3/43367).

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  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, 9177948974, Mashhad, Iran

    Arezou Mohammadinezhad & Batool Akhlaghinia

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  1. Arezou Mohammadinezhad
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  2. Batool Akhlaghinia
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Correspondence to Batool Akhlaghinia.

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Mohammadinezhad, A., Akhlaghinia, B. CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions. Catal Lett 150, 332–352 (2020). https://doi.org/10.1007/s10562-019-03070-5

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