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New Palladium(II)-Complex Based on Nitrogen Rich Ligand Efficient Precatalyst for C–C Cross-Coupling in Water Under Microwaves Irradiation

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Abstract

A new phosphine-free pyrimidylformamidine-based ligand and its palladium(II) complex has been synthesized from easily accesible staring materials and its ability to be a catalyst for cross-coupling reactions namely Suzuki–Miyaura (SMC) has been investigated. Firstly, the precatalyst was examined in cross-coupling of phenylboronic acid and p-bromoacetophenone which is selected due to its reactivity and as a low cost bromide that could be used for model cross-coupling reaction. The new palladium(II) complex showed high applicability as a precatalyst for SMC of aryl halides with various derivatives of boronic acid in water under conventional and microwaves irradiation conditions and the cross coupled products were obtained in excellent yields under mild reaction conditions.

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References

  1. B.C. Barnard, Palladium-catalysed C-C coupling: then and now. Platin. Met. Rev. 52, 38–45 (2008)

    CAS  Google Scholar 

  2. F. Bellina, A. Carpita, R. Rossi, Synthesis 2004(15), 2419–2440 (2004)

    Google Scholar 

  3. T. Seçkin, S. Köytepe, S. Demir, I. Özdemir, B. Cetinkaya, J. Inorg. Organomet. Polym. 13, 223–235 (2003)

    Google Scholar 

  4. A. Suzuki, J. Organomet. Chem. 653, 83–90 (2002)

    CAS  Google Scholar 

  5. M. Shibasaki, C.D. Boden, A. Kojima, Tetrahedron. 53, 7371–7395 (1997)

    CAS  Google Scholar 

  6. R. Martin, S.L. Buchwald, Acc. Chem. Res. 41(11), 1461–1473 (2008)

    CAS  PubMed  PubMed Central  Google Scholar 

  7. N.T.S. Phan, M.V. Sluys, C.W. Jones, Adv. Synth. Catal. 348(6), 609–679 (2006)

    CAS  Google Scholar 

  8. S.T. Laughlin, C.R. Bertozzi, Nat. Protoc. 2, 2930–2944 (2007)

    CAS  PubMed  Google Scholar 

  9. D. Zim, A.S. Gruber, G. Ebeling, J. Dupont, A.L. Monteiro, Org. Lett. 2, 2881–2884 (2000)

    CAS  PubMed  Google Scholar 

  10. L. Botella, C. Nájera, Angew. Chem. Int. Ed. 41, 179–181 (2002)

    CAS  Google Scholar 

  11. D. Yang, Y.-C. Chen, N.-Y. Zhu, Org. Lett. 6, 1577–1580 (2004)

    CAS  PubMed  Google Scholar 

  12. G.I. Dzhardimalieva, I.E. Uflyand, J. Inorg. Organomet. Polym. 28, 1305–1393 (2018)

    CAS  Google Scholar 

  13. O. Levy-Ontman, D. Blum, R. Golden, E. Pierschel, S. Leviev, J. Inorg. Organomet. Polym. 30, 622–636 (2020)

    CAS  Google Scholar 

  14. R.J. Kalbasi, N. Mosaddegh, J. Inorg. Organomet. Polym. 22, 404–414 (2012)

    CAS  Google Scholar 

  15. P.C.B. Page, B.R. Buckley, S.D. Christie, M. Edgar, A.M. Poulton, M.R. Elsegood, V. McKee, Organomet. Chem. 690, 6210–6216 (2005)

    CAS  Google Scholar 

  16. G.N. Babu, S. Pal, Tetrahedron. Lett. 58, 1000–1005 (2017)

    CAS  Google Scholar 

  17. A. Kumbhar, J. Organomet. Chem. 848, 22–88 (2017)

    CAS  Google Scholar 

  18. R. Asselt, C. Elsevier, J. Organomet. 13, 1972–1980 (1994)

    Google Scholar 

  19. S.M. Islam, P. Mondal, K. Tuhina, A.S. Roy, S. Mondal, D. Hossain, J. Inorg. Organomet. Polym. 20, 264–277 (2010)

    CAS  Google Scholar 

  20. A. Karadağ, A. Şenocak, Y. Yerli, E. Şahin, R. Topkaya, J. Inorg. Organomet. Polym. 22, 369–378 (2012)

    Google Scholar 

  21. M.G. Zarooni, S.J. Hoseini, M. Bahrami, M. Roushani, S.M. Nabavizadeh, J. Inorg. Organomet. Polym. (2020)

    Article  Google Scholar 

  22. P. Lidström, J. Tierney, B. Wathey, J. Westman, Tetrahedron 57, 9225–9283 (2001)

    Google Scholar 

  23. C.O. Kappe, A. Stadler, D. Dallinger, Microwaves in Organic and Medicinal Chemistry (Wiley, Hoboken, 2012)

    Google Scholar 

  24. A. de la Hoz, A. Diaz-Ortiz, A. Moreno, Chem. Soc. Rev. 34, 164–178 (2005)

    PubMed  Google Scholar 

  25. K.S. Salih, Y. Baqi, Catalysts 10, 4 (2020)

    Google Scholar 

  26. A.Y. Khormi, T.A. Farghaly, M.R. Shaaban, Heliyon 5, e01367 (2019)

    PubMed  PubMed Central  Google Scholar 

  27. K.M. Dawood, A.F. Darweesh, M.R. Shaaban, A.M. Farag, Arkivoc v, 348–358 (2018)

    Google Scholar 

  28. M.R. Shaaban, T.A. Farghaly, A.Y. Khormi, A.M. Farag, Curr. Org. Chem. 23(15), 1601–1662 (2019)

    CAS  Google Scholar 

  29. A.F. Darweesh, M.R. Shaaban, A.M. Farag, P. Metz, K.M. Dawood, Synthesis 2010, 3163–3173 (2010)

    Google Scholar 

  30. M.R. Shaaban, A.F. Darweesh, K.M. Dawood, A.M. Farag, Arkivoc x, 208–225 (2010)

    Google Scholar 

  31. B.D. Cullity, Elements of X-ray Diffraction (Addison, Wesley, 1978)

    Google Scholar 

  32. V. Farina, Adv. Synth. Catal. 346, 1553–1582 (2004)

    CAS  Google Scholar 

  33. J. Louie, J.F. Hartwig, Angewandte Chemie International Edition in English 35, 2359–2361 (1996)

    CAS  Google Scholar 

  34. A. Larina, V. Lokshin, J. Berthet, S. Delbaere, G. Vermeersch, V. Khodorkovsky, Tetrahedron 66, 8291–8299 (2010)

    CAS  Google Scholar 

  35. H. Bredereck, F. Effenberger, H. Botsch, H. Rehn, Chem. Ber. 98, 1081–1086 (1965)

    CAS  Google Scholar 

  36. L. Zhu, J. Duquette, M. Zhang, J. Org. Chem. 68, 3729–3732 (2003)

    CAS  PubMed  Google Scholar 

  37. W.F. Huber, M. Renoll, A.G. Rossow, D.T. Mowry, J. Am. Chem. Soc. 68, 1109–1112 (1946)

    CAS  Google Scholar 

  38. S. Duan, Y. Xu, X. Zhang, X. Fan, Chem. Commun. 52, 10529–10532 (2016)

    CAS  Google Scholar 

  39. M. Minabe, K. Watanabe, Y. Ayabe, M. Yoshida, T. Toda, J. Org. Chem. 52, 1745–1748 (1987)

    CAS  Google Scholar 

  40. A. Fodor, A. Magyar, D. Barczikai, L. Pirault-Roy, Z. Hell, Catal. Lett 145, 834–839 (2015)

    CAS  Google Scholar 

  41. H. Peng, Y.-Q. Chen, S.-L. Mao, Y.-X. Pi, Y. Chen, Z.-Y. Lian, T. Meng, S.-H. Liu, G.-A. Yu, Org. Biomol. Chem. 12, 6944–6952 (2014)

    CAS  PubMed  Google Scholar 

  42. B. Tao, D.W. Boykin, J. Org. Chem. 69, 4330–4335 (2004)

    CAS  PubMed  Google Scholar 

  43. N. Kataoka, Q. Shelby, J.P. Stambuli, J.F. Hartwig, J. Org. Chem. 67, 5553–5566 (2002)

    CAS  PubMed  Google Scholar 

  44. S. Marchais-Oberwinkler, P. Kruchten, M. Frotscher, E. Ziegler, A. Neugebauer, U. Bhoga, E. Bey, U. Müller-Vieira, J. Messinger, H. Thole, J. Med. Chem. 51, 4685–4698 (2008)

    CAS  PubMed  Google Scholar 

  45. J.S. Freundlich, H.E. Landis, Tetrahedron Lett. 47, 4275–4279 (2006)

    CAS  Google Scholar 

  46. M.A. McLaughlin, D.M. Barnes, Tetrahedron Lett. 47, 9095–9097 (2006)

    CAS  Google Scholar 

  47. N. Mejías, R. Pleixats, A. Shafir, M. Medio-Simón, G. Asensio, Eur. J. Org. Chem. 26, 5090–5099 (2010)

    Google Scholar 

  48. C. Desmarets, R. Omar-Amrani, A. Walcarius, J. Lambert, B. Champagne, Y. Fort, R. Schneider, Tetrahedron 64, 372–381 (2008)

    CAS  Google Scholar 

  49. M. Kienle, P. Knochel, Org. Lett. 12, 2702–2705 (2010)

    CAS  PubMed  Google Scholar 

  50. K.M. Dawood, M.M. El-Deftar, ARKIVOC ix, 319–330 (2010)

    Google Scholar 

  51. G.A. Molander, L. Iannazzo, J. Org. Chem. 76, 9182–9187 (2011)

    CAS  PubMed  PubMed Central  Google Scholar 

  52. H. Ding, Y. Chen, W. Cao, K. Wu, J. Chen, A.W. Lee, Synth. Commun. 40, 984–991 (2010)

    CAS  Google Scholar 

  53. E. Alacid, C. Najera, Org. Lett. 10, 5011–5014 (2008)

    CAS  PubMed  Google Scholar 

  54. L. Ackermann, A. Althammer, Org. Lett. 8, 3457–3460 (2006)

    CAS  PubMed  Google Scholar 

  55. H. Zhao, Y. Wang, J. Sha, S. Sheng, M. Cai, Tetrahedron 64, 7517–7523 (2008)

    CAS  Google Scholar 

  56. S.R. Borhade, S.B. Waghmode, Indian J. Chem. 49B, 565–572 (2010)

    CAS  Google Scholar 

  57. T.M. Razler, Y. Hsiao, F. Qian, R. Fu, R.K. Khan, W. Doubleday, J. Org. Chem. 74, 1381–1384 (2008)

    Google Scholar 

  58. S.E. Denmark, R.C. Smith, S.A. Tymonko, Tetrahedron 63, 5730–5738 (2007)

    CAS  PubMed  PubMed Central  Google Scholar 

Download references

Acknowledgements

Authors of the present work thanks the Deanship of Scientific Research (DSR) at Umm Al-Qura University (UQU) for supporting this proposal (Project code: 18-SCI-5-06-0007).

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Khormi, A.Y., Farghaly, T.A. & Shaaban, M.R. New Palladium(II)-Complex Based on Nitrogen Rich Ligand Efficient Precatalyst for C–C Cross-Coupling in Water Under Microwaves Irradiation. J Inorg Organomet Polym 30, 5133–5147 (2020). https://doi.org/10.1007/s10904-020-01620-8

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