Skip to main content
SpringerLink
Log in

A green and efficient Pd-free protocol for the Suzuki–Miyaura cross-coupling reaction using Fe3O4@APTMS@Cp2ZrClx(x = 0, 1, 2) MNPs in PEG-400

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this paper, a new application of the Fe3O4@APTMS@Cp2ZrClx(x = 0, 1, 2) MNPs as a robust and highly efficient Pd-free catalytic system in the environmentally benign Suzuki–Miyaura cross-coupling reaction has been demonstrated. The use of the recyclable Pd-free catalyst and PEG-400 as a green solvent, relatively short and acceptable reaction times, and good-to-excellent yields of the pure bi-aryl products are some of the salient features of the current carbon–carbon cross-coupling synthetic strategy.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 3
Fig. 9

Similar content being viewed by others

References

  1. L. Huang, L.K.G. Ackerman, K. Kang, A.M. Parsons, D.J. Weix, J. Am. Chem. Soc. 141, 10978 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. G.P. McGlacken, L.M. Bateman, Chem. Soc. Rev. 38, 2447 (2009)

    Article  CAS  PubMed  Google Scholar 

  3. D. Alberico, M.E. Scott, M. Lautens, Chem. Rev. 107, 174 (2007)

    Article  CAS  PubMed  Google Scholar 

  4. D. Saporito, S.A. Rodriquez, M.T. Baumgartner, Aust. J. Chem. 72, 978 (2019)

    Article  CAS  Google Scholar 

  5. M. Oi, R. Takita, J. Kanazawa, A. Muranaka, C. Wang, M. Uchiyama, Chem. Sci. 10, 107 (2019)

    Article  Google Scholar 

  6. M. Gholinejad, Z. Naghshbandi, C. Nájera, ChemCatChem 11, 1792 (2019)

    Article  CAS  Google Scholar 

  7. S.K. Das, B.K. Chandra, R.A. Molla, M. Sengupta, S.M. Islam, A. Majee, A. Bhaumik, Mol. Catal. 480, 110650 (2020)

    Article  CAS  Google Scholar 

  8. N.D. Patel, J.D. Sieber, S. Tcyrulinkov, B.J. Simmons, D. Rivalti, K. Duvvuri, Y. Zhang, D.A. Gao, K.R. Fandrick, N. Haddad, K.S. Lao, H.P.R. Mangunuru, S. Biswas, B. Qu, N. Grinberg, S. Pennino, H. Lee, J.J. Song, B.F. Gupton, N.K. Garg, M.C. Kozlowski, C.H. Senanayake, ACS Catal. 8, 10190 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. K. Liu, N. Li, Y. Ning, C. Zhu, J. Xie, Chem 5, 2718 (2019)

    Article  CAS  Google Scholar 

  10. A. Music, A.N. Baumann, P. Spieß, A. Plantefol, T.C. Jagau, D. Didier, J. Am. Chem. Soc. 142, 4341 (2020)

    Article  CAS  PubMed  Google Scholar 

  11. I.P. Beletskaya, F. Alonso, V. Tyurin, Coord. Chem. Rev. 385, 137 (2019)

    Article  CAS  Google Scholar 

  12. Y. Liu, B. Lou, L. Shangguan, J. Cai, H. Zhu, B. Shi, Macromolecules 51, 1351 (2018)

    Article  CAS  Google Scholar 

  13. N. Kaloğlu, İ. Özdemir, Tetrahedron 75, 2306 (2019)

    Article  CAS  Google Scholar 

  14. C. Torbog, M. Beller, Adv. Synth. Catal. 351, 3027 (2009)

    Article  CAS  Google Scholar 

  15. M.J. Robb, S.-Y. Ku, C.J. Hawker, Adv. Mater. 25, 5686 (2013)

    Article  CAS  PubMed  Google Scholar 

  16. P. Devendar, R.-Y. Qu, W.-M. Kang, B. He, G.-F. Yang, J. Agric. Food Chem. 66, 8914 (2018)

    Article  CAS  PubMed  Google Scholar 

  17. A. Taheri Kal Koshvandi, M.M. Heravi, T. Momeni, Appl. Organomet. Chem. 32, e4210 (2018)

    Article  CAS  Google Scholar 

  18. P. Schäfer, T. Palacin, M. Sidera, S.P. Fletcher, Nat. Commun. 8, 15762 (2017)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  19. F. Li, Y. Hu, Y. Wang, C. Ma, J. Wang, J. Med. Chem. 60, 1580 (2017)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Z. Li, X. Zhang, J. Qin, Z. Tan, M. Han, G. Jin, Org. Process Res. Dev. 23, 1881 (2019)

    Article  CAS  Google Scholar 

  21. M. Baenziger, W. Pachinger, F. Stauffer, W. Zaug, Org. Process Res. Dev. 23, 1908 (2019)

    Article  CAS  Google Scholar 

  22. R. Beninatto, G. Borsato, O. De Lucchi, F. Fabris, V. Lucchini, E. Zendri, Dyes Pigments 96, 679 (2013)

    Article  CAS  Google Scholar 

  23. G. Dhanger, J.L. Serrano, C. Schulzke, K.C. Gunturu, A.R. Kapdi, ACS Omega 2, 3144 (2017)

    Article  CAS  Google Scholar 

  24. S. Thunga, S. Poshala, N. Anugu, R. Konakanchi, V. Satheesh, H.P. Kokatla, Tetrahedron Lett. 60, 2046 (2019)

    Article  CAS  Google Scholar 

  25. C. Quan, J. Liu, W. Sun, X. Cheng, Chem. Papers 74, 485 (2020)

    Article  CAS  Google Scholar 

  26. M.S. Ghasemzadeh, B. Akhlaghinia, Aust. J. Chem. 72, 674 (2019)

    Article  CAS  Google Scholar 

  27. J.M. Neely, M.J. Bezdek, P.J. Chirik, ACS Omega 2, 935 (2016)

    CAS  Google Scholar 

  28. D. Gonzalez, T. Martinot, T. Hudlicky, Tetrahedron Lett. 40, 3077 (1999)

    Article  CAS  Google Scholar 

  29. X. Yang, X. Dou, K. Müllen, Chem. Asian J. 3, 759 (2008)

    Article  CAS  PubMed  Google Scholar 

  30. D. Ma, Q. Wu, Tetrahedron Lett. 42, 5279 (2001)

    Article  CAS  Google Scholar 

  31. T.R. Richardson, C.A. Clarke, K.-L. Yu, Y.K. Yee, T.J. Bleisch, J.E. Lopez, S.A. Scott, N.E. Hughes, B.S. Muhell, C.W. Lugar, T.L. Moore, P.K. Shetler, R.W. Zink, J.J. Osborne, C. Montrose-Rafizadeh, N. Patel, A.G. Geiser, R.J.S. Galvin, J.A. Dodge, ACS Med. Chem. Lett. 2, 148 (2011)

    Article  CAS  PubMed  Google Scholar 

  32. S.B. Tailor, M. Manzotti, S. Asghar, B.J.S. Rowsell, S.L.J. Luckham, H.A. Sparkes, Organometallics 38, 1770 (2019)

    Article  CAS  Google Scholar 

  33. F. Mathias, M.D. Crozet, Y. Kabri, P. Vanelle, Synth. Commun. 48, 1213 (2018)

    Article  CAS  Google Scholar 

  34. K.-Y. Park, B.T. Kim, J.-N. Heo, Eur. J. Org. Chem. 2014, 164 (2014)

    Article  CAS  Google Scholar 

  35. T. Leermann, P.-E. Broutin, F.R. Leroux, F. Colobert, Org. Biomol. Chem. 10, 4095 (2012)

    Article  CAS  PubMed  Google Scholar 

  36. T. Konno, T. Diatoh, A. Noiri, J. Chae, T. Ishihara, Y. Yamanaka, Org. Lett. 6, 933 (2004)

    Article  CAS  PubMed  Google Scholar 

  37. M.A. Selepe, S.E. Drewes, F.R. van Heerdn, J. Nat. Prod. 73, 1680 (2010)

    Article  CAS  PubMed  Google Scholar 

  38. A. Gollner, P.A. Koutentis, Org. Lett. 12, 1352 (2010)

    Article  CAS  PubMed  Google Scholar 

  39. H.A. Ioannidou, A. Martin, A. Gollner, P.A. Koutentis, J. Org. Chem. 76, 7417 (2019)

    Google Scholar 

  40. B.E. Haug, W. Stensen, J.S. Svendsen, Bioorg. Med. Chem. Lett. 17, 2361 (2007)

    Article  CAS  PubMed  Google Scholar 

  41. M. Petrera, T. Wein, L. Allmendinger, M. Sindelar, J. Pabel, G. Höfner, K.T. Wanner, ChemMedChem 11, 519 (2016)

    Article  CAS  PubMed  Google Scholar 

  42. B. Cornelio, M. Laronze-Cochard, M. Ceruso, M. Ferraroni, G.A. Rance, F. Carta, A.N. Khlobystov, A. Fontana, C.T. Supuran, J. Sapi, J. Med. Chem. 59, 721 (2016)

    Article  CAS  PubMed  Google Scholar 

  43. Y. Nakama, O. Yoshida, M. Yoda, K. Araki, Y. Sawada, J. Nakamura, S. Xu, K. Miura, H. Maki, H. Arimoto, J. Med. Chem. 53, 2528 (2010)

    Article  CAS  PubMed  Google Scholar 

  44. Š. Starčević, P. Brožič, S. Turk, J. Cesar, T.L. Rižner, S. Gobec, J. Med. Chem. 54, 248 (2011)

    Article  PubMed  CAS  Google Scholar 

  45. J.W. Leahy, C.A. Buhr, H.W.B. Johnson, B.G. Kim, T.G. Baik, J. Cannoy, T.P. Forsyth, J.W. Jeong, M.S. Lee, S. Ma, K. Noson, L. Wang, M. Williams, J.M. Nuss, E. Brooks, P. Foster, L. Goon, N. Heald, C. Holst, C. Jeager, S. Lam, J. Lougheed, L. Nguyen, A. Plonowski, J. Song, T. Stout, X. Wu, M.F. Yakes, P. Yu, W. Zhang, P. Lamb, O. Raeber, J. Med. Chem. 55, 5467 (2012)

    Article  CAS  PubMed  Google Scholar 

  46. J.A. Covel, V.J. Santora, J.M. Smith, R. Hayashi, C. Gallardo, M.I. Weinhouse, J.B. Ibarra, J.A. Schultz, D.M. Park, S.A. Estrada, B.J. Hofilena, M.D. Pulley, B.M. Smith, A. Ren, M. Suarez, J. Frazer, J. Edwards, E.K. Hauser, J. Lorea, G. Semple, A.J. Grottick, J. Med. Chem. 52, 5603 (2009)

    Article  CAS  PubMed  Google Scholar 

  47. J.A. Christopher, P. Bamborough, C. Alder, A. Campbell, G.J. Cutler, K. Down, A.M. Hamadi, A.M. Jolly, J.K. Kerns, F.S. Lucas, G.W. Mellor, D.D. Miller, M.A. Morse, K.D. Pancholi, W. Rumsey, Y.E. Solanke, R. Williamson, J. Med. Chem. 52, 3098 (2009)

    Article  CAS  PubMed  Google Scholar 

  48. S. Röver, M. Andjelkovic, A. Bénardeau, E. Chaput, W. Guba, P. Hebeisen, S. Mohr, M. Nettekoven, U. Obst, W.F. Richter, C. Ullmer, P. Waldmeier, M.B. Wright, J. Med. Chem. 56, 9874 (2013)

    Article  PubMed  CAS  Google Scholar 

  49. N.H. Theodoulou, P. Bamborough, A.J. Bannister, I. Becher, R.A. Bit, K.H. Che, C.-W. Chung, A. Dittmann, G. Drewes, D.H. Drewry, L. Gordon, P. Grandi, M. Leveridge, M. Lindon, A.-M. Michon, J. Molnar, S.C. Robson, N.C.O. Tomkinson, T. Kouzarides, R.K. Prinjha, P.G. Humphreys, J. Med. Chem. 59, 1425 (2016)

    Article  CAS  PubMed  Google Scholar 

  50. Y. Deng, M. Su, D. Kang, X. Liu, Z. Wen, Y. Li, L. Qiu, B. Shen, Y. Duan, Y. Huang, J. Med. Chem. 61, 11341 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  51. R. Sakakibara, W. Sasaki, Y. Onda, M. Yamaguchi, H. Ushirogochi, Y. Hiraga, K. Sato, M. Nishio, Y. Egi, K. Takedomi, H. Shimizu, T. Ohbora, F. Akahoshi, J. Med. Chem. 61, 5594 (2018)

    Article  CAS  PubMed  Google Scholar 

  52. Y. Sang, S. Han, C. Pannecouque, E. De Clercq, C. Zhuang, F. Chen, J. Med. Chem. 62, 11430 (2019)

    Article  CAS  PubMed  Google Scholar 

  53. I. Kemker, C. Schnepel, D.C. Schröder, A. Marion, N. Sewald, J. Med. Chem. 62, 7417 (2019)

    Article  CAS  PubMed  Google Scholar 

  54. S.P. Kitney, F. Cheng, S. Khan, C.N. Hope, W. McNab, S.M. Kelly, Liq. Cryst. 38, 1027 (2011)

    Article  CAS  Google Scholar 

  55. J.-Y. Li, H. Huang, Bioconjugate Chem. 29, 3841 (2018)

    Article  CAS  Google Scholar 

  56. D. Wang, D. Astruc, Chem. Soc. Rev. 46, 816 (2017)

    Article  CAS  PubMed  Google Scholar 

  57. S. Meninno, ChemSusChem 13, 439 (2020)

    Article  CAS  PubMed  Google Scholar 

  58. P.T. Anastas, J.B. Zimmerman, Green Chem. 21, 6545 (2019)

    Article  CAS  Google Scholar 

  59. M. Rimaz, H. Mousavi, B. Khalili, L. Sarvari, J. Iran. Chem. Soc. 16, 1687 (2019)

    Article  CAS  Google Scholar 

  60. C.G.S. Lima, N.M. Moreira, M.W. Paixão, A.G. Corréa, Curr. Opin. Green Sustain. Chem. 15, 7 (2019)

    Article  Google Scholar 

  61. L. Rogers, K.F. Jensen, Green Chem. 21, 3481 (2019)

    Article  CAS  Google Scholar 

  62. M. Rimaz, H. Mousavi, B. Khalili, F. Aali, J. Chin. Chem. Soc. 65, 1389 (2018)

    Article  CAS  Google Scholar 

  63. H.C. Erythropel, J.B. Zimmerman, T.M. de Winter, L. Petitjean, F. Melnikov, C.H. Lam, A.W. Lounsbury, K.E. Mellor, N.Z. Janković, Q. Tu, L.N. Pincus, M.M. Falinski, W. Shi, P. Coish, D.L. Plata, P.T. Anastas, Green Chem. 20, 1929 (2018)

    Article  CAS  Google Scholar 

  64. M.C. Bryan, P.J. Dunn, D. Entwistle, F. Gallou, S.G. Koenig, J.D. Hayler, M.R. Hickey, S. Hughes, M.E. Kopach, G. Moine, P. Richardson, F. Roschangar, A. Steven, F.J. Weiberth, Green Chem. 20, 5082 (2018)

    Article  CAS  Google Scholar 

  65. M. Rimaz, H. Mousavi, M. Behnam, L. Sarvari, B. Khalili, Curr. Chem. Lett. 6, 55 (2017)

    Article  Google Scholar 

  66. M. Rimaz, J. Khalafi, H. Mousavi, S. Bohlooli, B. Khalili, J. Heterocyclic Chem. 54, 3174 (2017)

    Article  CAS  Google Scholar 

  67. R. Hudson, Y. Feng, R.S. Varma, A. Moores, Green Chem. 16, 4493 (2014)

    Article  CAS  Google Scholar 

  68. M.G. Dekamin, M. Azimoshan, L. Ramezani, Green Chem. 15, 811 (2013)

    Article  CAS  Google Scholar 

  69. B. Banerjee, ChemistrySelect 4, 2484 (2019)

    Article  CAS  Google Scholar 

  70. O. Mahé, J.-F. Brière, I. Dez, Eur. J. Org. Chem. 2015, 2559 (2015)

    Article  CAS  Google Scholar 

  71. P. Ghasemi, M. Yari, M.A. Zolfigol, A.A. Taherpour, M. Torabi, ACS Omega 5, 3207 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  72. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.-M. Basset, Chem. Rev. 111, 3036 (2011)

    Article  CAS  PubMed  Google Scholar 

  73. D. Wang, D. Astruc, Chem. Rev. 114, 6949 (2014)

    Article  CAS  PubMed  Google Scholar 

  74. S. Shylesh, V. Schünemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 3428 (2010)

    Article  CAS  Google Scholar 

  75. L.M. Rossi, N.J.S. Costa, F.P. Silva, R. Wojcieszak, Green Chem. 16, 2906 (2014)

    Article  CAS  Google Scholar 

  76. B. Karimi, F. Mansouri, H.M. Mirzaei, ChemCatChem 7, 1736 (2015)

    Article  CAS  Google Scholar 

  77. P. Akbarzadeh, N. Koukabi, E. Kolvari, Res. Chem. Intermed. 45, 1009 (2019)

    Article  CAS  Google Scholar 

  78. M. Gholamhosseini-Nazari, S. Esmati, K.D. Safa, A. Khataee, R. Teimuri-Mofrad, Res. Chem. Intermed. 45, 1841 (2019)

    Article  CAS  Google Scholar 

  79. M.M. Khodaei, A. Alizadeh, M. Haghipour, Res. Chem. Intermed. 45, 2727 (2019)

    Article  CAS  Google Scholar 

  80. M.A. Karimi Zarchi, S.S.A. Darbandizadeh Mohammad Abadi, Res. Chem. Intermed. 45, 2605 (2019)

    Article  CAS  Google Scholar 

  81. L. Mohammadi, M.A. Zolfigol, M. Yarie, M. Ebrahiminia, K.P. Roberts, S.R. Hussaini, Res. Chem. Intermed. 45, 4789 (2019)

    Article  CAS  Google Scholar 

  82. N. Mohammadian, B. Akhlaghinia, Res. Chem. Intermed. 45, 4737 (2019)

    Article  CAS  Google Scholar 

  83. H. Mohammadi, H.R. Shaterian, Res. Chem. Intermed. 46, 179 (2020)

    Article  CAS  Google Scholar 

  84. M.M. Khodaei, A. Alizadeh, M. Haghipour, Res. Chem. Intermed. 46, 1033 (2020)

    Article  CAS  Google Scholar 

  85. S. Asadbegi, M.A. Bodaghifard, A. Mobinkhaledi, Res. Chem. Intermed. 46, 1629 (2020)

    Article  CAS  Google Scholar 

  86. H. Foroughi Nia, N. Hazeri, M. Rezaie Kahkhaie, M.T. Maghsoodlou, Res. Chem. Intermed. 46, 1685; (2020)

  87. A. Mazaheri, M. Bostanian, Res. Chem. Intermed. 46, 2327 (2020)

    Article  CAS  Google Scholar 

  88. Y. Chen, T. Wu, G. Xing, Y. Kou, B. Li, X. Wang, M. Gao, L. Chen, Y. Wang, J. Yang, Y. Li, Y. Zhang, W. Wang, Ind. Eng. Chem. Res. 58, 15151 (2019)

    Article  CAS  Google Scholar 

  89. Y. Rangraz, F. Nemati, A. Elhampour, Ind. Eng. Chem. Res. 58, 17308 (2019)

    Article  CAS  Google Scholar 

  90. Y. Ren, H. Li, W. Yang, D. Shi, Q. Wu, Z. Zhao, C. Feng, H. Liu, Q. Jiao, Ind. Eng. Chem. Res. 58, 2824 (2019)

    Article  CAS  Google Scholar 

  91. A. Fakhri, A. Naghipour, Trans. Met. Chem. 43, 463 (2018)

    Article  CAS  Google Scholar 

  92. S.M. Mousavifar, H. Kefayati, S. Shariati, J. Heterocyclic Chem. 57, 157 (2020)

    Article  CAS  Google Scholar 

  93. A.K. Sharma, H. Joshi, A.K. Singh, RSC Adv. 10, 6452 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  94. A.G. Naikwade, M.B. Jagadale, D.P. Kale, A.D. Gophane, K.M. Garadkar, G.S. Rashinkar, ACS Omega 5, 131 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  95. F. Rezaei, M.A. Amrollahi, R. Khalifeh, ChemistrySelect 5, 1760 (2020)

    Article  CAS  Google Scholar 

  96. W. Xie, H. Wang, Renew. Energy 145, 1709 (2020)

    Article  CAS  Google Scholar 

  97. M. Esmatzadeh, S. Sadjadi, Z. Salehi, Int. J. Biol. Macromol. 150, 441 (2020)

    Article  CAS  Google Scholar 

  98. M. Bystrzanowska, P. Petkov, M. Tobiszewski, ACS Sustain. Chem. Eng. 7, 18434 (2019)

    Article  CAS  Google Scholar 

  99. P.G. Jessop, Green Chem. 13, 1391 (2011)

    Article  CAS  Google Scholar 

  100. R.K. Henderson, C. Jiménez-González, D.J.C. Constable, S.R. Alston, G.G.A. Inglis, G. Fisher, J. Sherwood, S.P. Binks, A.D. Curzons, Green Chem. 13, 854 (2011)

    Article  CAS  Google Scholar 

  101. J.H. Clark, S.J. Tavener, Org. Process Res. Dev. 11, 149 (2007)

    Article  CAS  Google Scholar 

  102. M. Rimaz, J. Khalafi, H. Mousavi, Res. Chem. Intermed. 42, 8185 (2016)

    Article  CAS  Google Scholar 

  103. W. Xie, T. Li, C. Chen, H. Wu, S. Liang, H. Chang, B. Liu, E. Drioli, Q. Wang, J.C. Crittenden, Ind. Eng. Chem. Res. 58, 6413 (2019)

    Article  CAS  Google Scholar 

  104. R.A. Sheldon, Curr. Opin. Green Sustain. Chem. 18, 13 (2019)

    Article  Google Scholar 

  105. G. Náray-Szabó, L.T. Mika, Green Chem. 20, 2171 (2018)

    Article  Google Scholar 

  106. C.J. Clarke, W.-C. Tu, O. Levers, A. Bröhl, J.P. Hallet, Chem. Rev. 118, 747 (2018)

    Article  CAS  PubMed  Google Scholar 

  107. J. Chen, S.K. Spear, J.G. Huddleston, R.D. Rogers, Green Chem. 7, 64 (2005)

    Article  CAS  Google Scholar 

  108. M. Vafaeezadeh, M. Mahmoodi Hashemi, J. Mol. Liq. 207, 73 (2015)

    Article  CAS  Google Scholar 

  109. S.G. Balwe, K.T. Lim, B.G. Cho, Y.T. Jeong, Tetrahedron 73, 3564 (2017)

    Article  CAS  Google Scholar 

  110. A. Nagaraju, B.J. Ramulu, G. Shukla, A. Srivastava, G.K. Verma, K. Raghunvanshi, M.S. Singh, Green Chem. 17, 950 (2015)

    Article  CAS  Google Scholar 

  111. H. Mousavi, B. Zeynizadeh, R. Younesi, M. Esmati, Aust. J. Chem. 71, 595 (2018)

    Article  CAS  Google Scholar 

  112. B. Zeynizadeh, R. Younesi, H. Mousavi, Res. Chem. Intermed. 44, 7331 (2018)

    Article  CAS  Google Scholar 

  113. B. Zenizadeh, F. Mohammad Aminzadeh, H. Mousavi, Res. Chem. Intermed. 45, 3329 (2019)

    Article  CAS  Google Scholar 

  114. B. Zeynizadeh, H. Mousavi, S. Zarrin, J. Chin. Chem. Soc. 66, 928 (2019)

    Article  CAS  Google Scholar 

  115. B. Zeynizadeh, F. Mohammad Aminzadeh, H. Mousavi, Green Process. Synth. 8, 742 (2019)

    Article  CAS  Google Scholar 

  116. R. Bakhshi, B. Zeynizadeh, H. Mousavi, J. Chin. Chem. Soc. 67, 623 (2020)

    Article  CAS  Google Scholar 

  117. B. Zeynizadeh, F. Sepehraddin, H. Mousavi, Ind. Eng. Chem. Res. 58, 16379 (2019)

    Article  CAS  Google Scholar 

  118. F.Y. Zhou, K.J. Qiu, D. Bian, Y.F. Zheng, J.P.A. Lin, J. Mater. Sci. Technol. 30, 299 (2014)

    Article  CAS  Google Scholar 

  119. Y. Dong, J.-J. Jv, Y. Li, W.-H. Li, Y.-Q. Chen, Q. Sun, J.-P. Ma, Y.-B. Dong, RSC Adv. 9, 20266 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  120. M. Arghan, N. Koukabi, E. Kolvari, Appl. Organomet. Chem. 33, e5075 (2019)

    Article  CAS  Google Scholar 

  121. F. Raoufi, M. Monajjemi, H. Aghaei, K. Zare, M. Ghaedi, ChemistrySelect 5, 211 (2020)

    Article  CAS  Google Scholar 

  122. V. Sadhasivam, B. Sankar, G. Elamathi, M. Mariyappan, A. Siva, Res. Chem. Intermed. 46, 681 (2020)

    Article  CAS  Google Scholar 

  123. M.M. Khodaei, M. Dehghan, Polyhedron 162, 219 (2019)

    Article  CAS  Google Scholar 

  124. A. Ghorbani-Choghamarani, M. Mohammadi, Z. Taherinia, J. Iran. Chem. Soc. 16, 411 (2019)

    Article  CAS  Google Scholar 

  125. P. Fakhri, M. Nasrollahzadeh, B. Jaleh, RSC Adv. 4, 48691 (2014)

    Article  CAS  Google Scholar 

  126. A.R. Hajipour, P. Abolfathi, New J. Chem. 41, 2386 (2017)

    Article  CAS  Google Scholar 

  127. M. Rajabzadeh, R. Khalifeh, H. Eshghi, M. Bakavoli, J. Catal. 360, 261 (2018)

    Article  CAS  Google Scholar 

  128. M. Dabiri, N. Farajinia Lehi, S. Kazemi Movahed, Catal. Lett. 146, 1674 (2016)

    Article  CAS  Google Scholar 

  129. S. Kazemi Movahed, M. Shariatpour, M. Dabiri, RSC Adv. 5, 33423 (2015)

    Article  CAS  Google Scholar 

  130. J. Mao, J. Guo, F. Fang, S.-J. Ji, Tetrahedron 64, 3905 (2008)

    Article  CAS  Google Scholar 

  131. K. Ghosh, K. Tuhina, S.M. Islam, J. Colloid Interface Sci. 459, 97 (2015)

    Article  PubMed  CAS  Google Scholar 

  132. H.-F. Zhang, J. Med. Chem. Sci. 2, 38 (2019)

    CAS  Google Scholar 

  133. K. Ghosh, S.K. Kundu, S.R. Roy, P. Monal, K. Ghosh, A. Bhaumik, S.M. Islam, Dalton Trans. 43, 7057 (2014)

    Article  PubMed  Google Scholar 

  134. M. Gopiraman, S. Saravanamoorthy, S. Ullah, A. Ilangovan, I.S. Kim, I.M. Chung, RSC Adv. 10, 2545 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  135. A. Pourjavadi, N. Keshavarzi, F. Matloubi Moghaddam, S.H. Hosseini, ChemistrySelect 3, 2716 (2018)

    Article  CAS  Google Scholar 

  136. M. Shahabi Nejad, N. Seyedi, H. Sheibani, S. Behzadi, Mol. Divers. 23, 527 (2019)

    Article  CAS  PubMed  Google Scholar 

  137. M. Thomas, M.U.D. Sheikh, D. Ahirwar, M. Bano, F. Khan, J. Colloid Interface Sci. 505, 115 (2017)

    Article  CAS  PubMed  Google Scholar 

  138. D.K. Dumbre, P.N. Yadav, S.K. Bhargava, V.R. Choudhary, J. Catal. 301, 134 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to the Research Council of Urmia University for partial support of this research.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran

    Behzad Zeynizadeh, Hossein Mousavi & Farhad Sepehraddin

Authors
  1. Behzad Zeynizadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hossein Mousavi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Farhad Sepehraddin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hossein Mousavi.

Ethics declarations

Conflict of interest

The authors declare no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 17 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zeynizadeh, B., Mousavi, H. & Sepehraddin, F. A green and efficient Pd-free protocol for the Suzuki–Miyaura cross-coupling reaction using Fe3O4@APTMS@Cp2ZrClx(x = 0, 1, 2) MNPs in PEG-400. Res Chem Intermed 46, 3361–3382 (2020). https://doi.org/10.1007/s11164-020-04145-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04145-4

Keywords

Search

Navigation