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Palladium-free and phosphine-free Sonogashira coupling reaction of aryl halides with terminal alkynes catalyzed by boehmite nanoparticle-anchored Cu(I) diethylenetriamine complex

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Abstract

In this work, a novel diethylenetriamine-functionalized-boehmite nanoparticle-supported Cu(I) catalyst is synthesized. The catalyst prepared is then characterized by FT-IR spectroscopy, scanning electron microscopy, transmission electron microscopy, X-ray diffraction spectroscopy, and inductively coupled plasma techniques. The catalyst prepared shows great activity in the Sonogashira coupling reaction of aryl halides with terminal alkynes in DMF under an argon atmosphere. Moreover, it could be removed from the reaction mixture by means of simple filtration and used again for up to six runs without an appreciable loss in its activity.

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References

  1. S. Yu, A. Haight, B. Kotecki, L. Wang, K. Lukin, D.R. Hill, J. Org. Chem. 74, 9539 (2009)

    Article  CAS  Google Scholar 

  2. J.Z. Liu, J.W.Y. Lam, B.Z. Tang, Chem. Rev. 109, 5799 (2009)

    Article  CAS  Google Scholar 

  3. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 16, 4467 (1975)

    Article  Google Scholar 

  4. R. Chinchilla, C. Nájera, Chem. Soc. Rev. 40, 5084 (2011)

    Article  CAS  Google Scholar 

  5. C.X. Lin, J.F. Zhu, Q.S. Li, L.H. Ao, Y.J. Jin, F.B. Xu, F.Z. Hu, Y.F. Yuan, Appl. Organomet. Chem. 28, 298 (2014)

    Article  CAS  Google Scholar 

  6. J.P. Wan, S. Cao, Y.F. Jing, Appl. Organomet. Chem. 28, 631 (2014)

    Article  CAS  Google Scholar 

  7. L.H. Zou, A.J. Johansson, E. Zuidema, C. Bolm, Chem. Eur. J. 19, 8144 (2013)

    Article  CAS  Google Scholar 

  8. T.Y. Li, X.M. Qu, G.L. Xie, J.C. Mao, Chem. Asian J. 61, 325 (2011)

    Google Scholar 

  9. L. Feng, F. Liu, P. Sun, J. Bao, Synlett 16, 1415 (2008)

    Google Scholar 

  10. M. Chandra, R. Volla, P. Vogel, Tetrahedron Lett. 49, 5961 (2008)

    Article  Google Scholar 

  11. G. Fang, X. Bi, Chem. Soc. Rev. 44, 8124 (2015)

    Article  CAS  Google Scholar 

  12. L. Wang, P. Li, Y. Zhang, Chem. Commun. 514 (2004)

  13. S. Park, M. Kim, D.H. Koo, S. Chang, Adv. Synth. Catal. 346, 1638 (2004)

    Article  CAS  Google Scholar 

  14. S. Garbacia, R. Touzani, O. Lavastre, J. Comb. Chem. 6, 297 (2004)

    Article  CAS  Google Scholar 

  15. A. Corma, R. Juárez, M. Boronat, F. Sánchez, M. Iglesias, H. García, Chem. Commun. 47, 1446 (2011)

    Article  CAS  Google Scholar 

  16. T. Lauterbach, M. Livendahl, A. Rosellón, P. Espinet, A.M. Echavarren, Org. Lett. 12, 3006 (2010)

    Article  CAS  Google Scholar 

  17. D. Ma, F. Liu, Chem. Commun. 1934 (2004)

  18. P. Saejueng, C.G. Bates, D. Venkataraman, Synthesis 111, 1706 (2005)

    Google Scholar 

  19. J.-H. Li, J.-L. Li, D.-P. Wang, S.-F. Pi, Y.-X. Xie, M.-B. Zhang, X.-C. Hu, J. Org. Chem. 72, 2053 (2007)

    Article  CAS  Google Scholar 

  20. E. Zuidema, C. Bolm, Chem. Eur. J. 16, 4181 (2010)

    Article  CAS  Google Scholar 

  21. J. Mao, J. Guo, S. Ji, J. Mol. Catal. A. 284, 85 (2008)

    Article  CAS  Google Scholar 

  22. Y.F. Wang, W. Deng, L. Liu, Q.X. Guo, Chin. Chem. Lett. 16, 1197 (2005)

    CAS  Google Scholar 

  23. Y.-X. Xie, C.L. Deng, S.-F. Pi, J.-H. Li, D.-L. Yin, Chin. J. Chem. 24, 1290 (2006)

    Article  CAS  Google Scholar 

  24. F. Monnier, F. Turtaut, L. Duroure, M. Taillefer, Org. Lett. 10, 3203 (2008)

    Article  CAS  Google Scholar 

  25. M. Wu, J. Mao, J. Guo, S. Ji, Eur. J. Org. Chem. 111, 4050 (2008)

    Article  Google Scholar 

  26. H.-J. Chen, Z.-Y. Lin, M.-Y. Li, R.-J. Lian, Q.-W. Xue, J.-L. Chung, S.-C. Chen, Y.-J. Chen, Tetrahedron 66, 7755 (2010)

    Article  CAS  Google Scholar 

  27. B.C. Ranu, S. Bhadra, D. Saha, Curr. Org. Synth. 8, 146 (2011)

    Article  CAS  Google Scholar 

  28. L. Yin, J. Liebscher, Chem. Rev. 107, 133 (2007)

    Article  CAS  Google Scholar 

  29. V. Polshethiwar, C. Len, A. Fihri, Coord. Chem. Rev. 253, 2599 (2009)

    Article  Google Scholar 

  30. M.B. Thathagar, J. Beckers, G. Rothenberg, Green Chem. 6, 215 (2004)

    Article  CAS  Google Scholar 

  31. A. Biffis, E. Scattolin, N. Ravasio, F. Zaccheria, Tetrahedron Lett. 48, 8761 (2007)

    Article  CAS  Google Scholar 

  32. D. Saha, T. Chatterjee, M. Mukherjee, B.C. Ranu, J. Org. Chem. 77, 9379 (2012)

    Article  CAS  Google Scholar 

  33. H. Zhao, B. Huang, Y. Wu, M. Cai, J. Organomett. Chem. 797, 21 (2015)

    Article  CAS  Google Scholar 

  34. M.M. Amini, M. Mirzaee, J. Sol Gel Sci. Technol. 36, 19 (2005)

    Article  CAS  Google Scholar 

  35. A. Ghorbani-Choghamarani, B. Tahmasbi, F. Arghand, S. Faryadi, RSC Adv. 5, 92174 (2015)

    Article  CAS  Google Scholar 

  36. M. Hajjami, A. Ghorbani-Choghamarani, R. Ghafouri-Nejad, B. Tahmasbi, New J. Chem. 40, 3066 (2016)

    Article  CAS  Google Scholar 

  37. A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, RSC Adv. 6, 56638 (2016)

    Article  CAS  Google Scholar 

  38. M. Mirzaee, B. Bahramian, A. Amoli, Appl. Organomet. Chem. 29, 593 (2015)

    Article  CAS  Google Scholar 

  39. M. Mirzaee, B. Bahramian, M. Mirebrahimi, Chin. J. Catal. 37, 1263 (2016)

    Article  CAS  Google Scholar 

  40. M. Mirzaee, B. Bahramian, A. Feizi, R. Gholami, Chem. Eng. J. 308, 160 (2017)

    Article  CAS  Google Scholar 

  41. A. Keivanloo, M. Bakherad, E. Imanifar, M. Mirzaee, Appl. Catal. A 467, 291 (2013)

    Article  CAS  Google Scholar 

  42. A. Keivanloo, M. Mirzaee, M. Bakherad, A. Soozani, Chin. J. Catal. 35, 362 (2014)

    Article  CAS  Google Scholar 

  43. M. Bakherad, A. Keivanloo, S. Samangooei, Chin. J. Catal. 3, 324 (2014)

    Article  Google Scholar 

  44. M. Bakherad, A. Keivanloo, S. Samangooei, M. Omidian, J. Organomet. Chem. 740, 78 (2013)

    Article  CAS  Google Scholar 

  45. M. Bakherad, B. Bahramian, S. Jajarmi, J. Organomet. Chem. 749, 405 (2014)

    Article  CAS  Google Scholar 

  46. M. Bakherad, S. Jajarmi, J. Mol. Catal. A Chem. 370, 152 (2013)

    Article  CAS  Google Scholar 

  47. T.P.B. Nguyen, J.-W. Lee, W.G. Shim, H. Moon, Microporous Mesoporous Mater. 110, 560 (2008)

    Article  CAS  Google Scholar 

  48. F. Durap, M. Rakap, M. Aydemir, S. Özkar, Appl. Catal. A 382, 339 (2010)

    Article  CAS  Google Scholar 

  49. D.B. Eremin, V.P. Ananikov, Coord. Chem. Rev. 346, 2 (2017)

    Article  CAS  Google Scholar 

  50. R.D. Stephens, C.E. Castro, J. Org. Chem. 28, 2163 (1963)

    Article  Google Scholar 

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Acknowledgements

We gratefully acknowledge the financial support of the Research Council of the Shahrood University of Technology.

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Authors and Affiliations

  1. School of Chemistry, Shahrood University of Technology, Shahrood, 3619995161, Iran

    Mohammad Bakherad, Rahele Doosti, Mahdi Mirzaee & Amir H. Amin

  2. Department of Chemistry, Shahid Beheshti University, Tehran, 1983963113, Iran

    Khosrow Jadidi & Omid Amiri

Authors
  1. Mohammad Bakherad
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  2. Rahele Doosti
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  3. Mahdi Mirzaee
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  4. Khosrow Jadidi
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  5. Amir H. Amin
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Correspondence to Mohammad Bakherad.

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Bakherad, M., Doosti, R., Mirzaee, M. et al. Palladium-free and phosphine-free Sonogashira coupling reaction of aryl halides with terminal alkynes catalyzed by boehmite nanoparticle-anchored Cu(I) diethylenetriamine complex. Res Chem Intermed 43, 7347–7363 (2017). https://doi.org/10.1007/s11164-017-3079-0

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