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The first use of [PdBr2(imidazolidin-2-ylidene)(pyridine)] catalysts in the direct C-H bond arylation of C2-substituted furan and thiophene

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Abstract

N-Heterocyclic carbene (NHC)-linked PEPPSI-type palladium complexes have recently been used in the direct C-H bond arylation of heteroarenes. However, in most of the published works, NHC ligands containing benzimidazole and imidazole ring have been used, but using NHC ligands containing saturated imidazoline ring is quite rare. Therefore, in this study, four new 1,3-disubstituted imidazolinium salts as NHC ligand precursors, and their four new PEPPSI-type palladium complexes were synthesized. The structures of all new compounds were fully characterized by different spectroscopic and analytical techniques. The more detailed structural characterization of one of the palladium complexes was determined by single-crystal X-ray diffraction study. The catalytic activities of all palladium complexes were evaluated in the direct C-H bond arylation of the 2-acetylfuran and 2-acetylthiophene with (hetero) aryl bromides and readily available and inexpensive aryl chlorides in presence of 1 mol% catalyst loading at 120 °C. Under the given conditions, (hetero)aryl halides were successfully applied as the arylating reagents to achieve the C5-arylated furans and thiophenes in acceptable to high yields.

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References

  1. W.A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 36, 2162 (1997)

    CAS  Google Scholar 

  2. W.A. Herrmann, Angew. Chem. Int. Ed. 41, 1290 (2002)

    CAS  Google Scholar 

  3. F.E. Hahn, M.C. Jahnke, Angew. Chem. Int. Ed. 47, 3122 (2008)

    CAS  Google Scholar 

  4. M.N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature 510, 485 (2014)

    CAS  PubMed  Google Scholar 

  5. D.J. Nelson, Eur. J. Inorg. Chem. 12, 2012 (2015)

    Google Scholar 

  6. S.-Z. Wu, Q. Yu, Y.-H. Li, G.-H. Cui, Res. Chem. Intermed. 47, 835 (2021)

    CAS  Google Scholar 

  7. S.P. Nolan (ed.), N-Heterocyclic Carbenes Effective Tools for Organometallic Synthesis (Wiley-VCH, Weinheim, 2014), p. 544

    Google Scholar 

  8. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, G.R.J. Artus, Angew. Chem. Int. Ed. 34, 2371 (1995)

    CAS  Google Scholar 

  9. E. Peris, Chem. Rev. 118, 9988 (2017)

    PubMed  Google Scholar 

  10. S. Díez-González, N. Marion, S.P. Nolan, Chem. Rev. 109, 3612 (2009)

    PubMed  Google Scholar 

  11. B. Liu, J. Li, F. Song, J. You, Chem. Eur. J. 18, 10830 (2012)

    CAS  PubMed  Google Scholar 

  12. M.E. Benhalouche, H. Li, A. Miloudi, A. Benzai, M. Cordier, J.-F. Soulé, H. Doucet, Eur. J. Org. Chem. 30, 4792 (2020)

    Google Scholar 

  13. J. Yang, Appl. Organometal. Chem. 34, e5450 (2020)

    CAS  Google Scholar 

  14. B. Eftekhari-Sis (ed.), Aromatic C(Sp2)-H Dehydrogenative Coupling Reactions: Heterocycles Synthesis (CRC Press, Boca Raton, 2019)

    Google Scholar 

  15. N. Amirmahani, N.O. Mahmoodi, M. Malakootian, A. Pardakhty, N. Seyedi, Res. Chem. Intermed. 46, 4595 (2020)

    CAS  Google Scholar 

  16. F. Jafari, A. Ghorbani-Choghamarani, N. Hasanzadeh, Res. Chem. Intermed. 47, 1033 (2021)

    CAS  Google Scholar 

  17. M. Miura, T. Satoh, Palladium-catalyzed direct arylation reactions, in Modern arylation methods. ed. by L. Ackermann (Wiley-VCH, Weinheim, 2009), pp. 335–361

    Google Scholar 

  18. J.-Q. Yu, Z. Shi (eds.), C-H Activation Topics in Current Chemistry (Springer, Berlin, Heidelberg, 2010)

    Google Scholar 

  19. X. Shi, E.D.S. Carrizo, M. Cordier, J. Roger, N. Pirio, J.-C. Hierso, P. Fleurat-Lessard, J.-F. Soulé, H. Doucet, Chem. Eur. J. 27, 1 (2021)

    Google Scholar 

  20. V. Dimakos, M.S. Taylor, Org. Biomol. Chem. 19, 514 (2021)

    CAS  PubMed  Google Scholar 

  21. Y. Kitamura, Y. Murata, M. Iwai, M. Matsumura, S. Yasuike, Molecules 26, 97 (2021)

    CAS  Google Scholar 

  22. F. Bellina, R. Rossi, Tetrahedron 65, 10259 (2009)

    Google Scholar 

  23. M. Kaloğlu, N. Kaloğlu, İ Yıldırım, N. Özdemir, İ Özdemir, J. Mol. Struc. 1206, 127668 (2020)

    Google Scholar 

  24. M. Kaloglu, S. Demir Dusunceli, I. Ozdemi, J. Organometal. Chem. 915, 121236 (2020)

    CAS  Google Scholar 

  25. S. Sreekumar, S. Xavier, A. Govindan, R.E. Thampikannu, K. Vellayan, B. González, Res. Chem. Intermed. 46, 4529 (2020)

    CAS  Google Scholar 

  26. C.B. Bheeter, L. Chen, J.-F. Soulé, H. Doucet, Catal. Sci. Technol. 6, 2005 (2016)

    CAS  Google Scholar 

  27. I.V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 36, 1173 (2007)

    CAS  PubMed  PubMed Central  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  29. L.-C. Campeau, D.R. Stuart, K. Fagnou, Aldrichimica Acta 40, 35 (2007)

    CAS  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  31. L. Ackermann, R. Vicente, A.R. Kapdi, Angew. Chem. Int. Ed. 48, 9792 (2009)

  32. L. Ackermann, Chem. Rev. 111, 1315 (2011)

    CAS  PubMed  Google Scholar 

  33. N. Nakamura, Y. Tajima, K. Sakai, Heterocycles 17, 235 (1982)

    CAS  Google Scholar 

  34. A. Ohta, Y. Akita, T. Ohkuwa, M. Chiba, R. Fukunaga, A. Miyafuji, T. Nakata, N. Tani, Y. Aoyagi, Heterocycles 31, 1951 (1990)

    CAS  Google Scholar 

  35. I.A. Stepek, K. Itami, ACS Materials Lett. 2, 951 (2020)

    CAS  Google Scholar 

  36. C.J. O’Brien, E.A.B. Kantchev, C. Valente, N. Hadei, G.A. Chass, A. Lough, A.C. Hopkinson, M.G. Organ, Chem. Eur. J. 12, 4743 (2006)

    CAS  PubMed  Google Scholar 

  37. F. Glorius (ed.), N-Heterocyclic Carbenes in Transition Metal Catalysis (Springer-Verlag, Berlin, 2007)

    Google Scholar 

  38. C. Valente, S. Çalimsiz, K.H. Hoi, D. Mallik, M. Sayah, M.G. Organ, Angew. Chem. Int. Ed. 51, 3314 (2012)

    CAS  Google Scholar 

  39. Q. Zhao, G. Meng, S.P. Nolan, M. Szostak, Chem. Rev. 120, 1981 (2020)

    CAS  PubMed  PubMed Central  Google Scholar 

  40. X.-X. He, Y. Li, B.B. Ma, Z. Ke, F.S. Liu, Organometallics 35, 2655 (2016)

    CAS  Google Scholar 

  41. L.Q. Hu, R.L. Deng, Y.F. Li, C.J. Zeng, D.S. Shen, F.S. Liu, Organometallics 37, 214 (2018)

    CAS  Google Scholar 

  42. A.R. Martin, A. Chartoire, A.M.Z. Slawin, S.P. Nolan, Beilstein J. Org. Chem. 8, 1637 (2012)

    CAS  PubMed  PubMed Central  Google Scholar 

  43. E.D. Coy, L.E. Cuca, M. Sefkow, Synth. Commun. 41, 41 (2010)

    Google Scholar 

  44. K.-T. Chan, Y.-H. Tsai, W.-S. Lin, J.-R. Wu, S.-J. Chen, F.-X. Liao, C.-H. Hu, H.M. Lee, Organometallics 29, 463 (2010)

    CAS  Google Scholar 

  45. S. Otsuka, H. Yorimitsu, A. Osuka, Chem. Eur. J. 21, 14703 (2015)

    CAS  PubMed  Google Scholar 

  46. W. Chen, J. Yang, J. Organometal. Chem. 872, 24 (2018)

    CAS  Google Scholar 

  47. M. Kaloğlu, İ Özdemir, Inorg. Chim. Acta 504, 119454 (2020)

    Google Scholar 

  48. M. Kaloğlu, N. Kaloğlu, İ Özdemir, Catal. Lett. (2021).

    Article  Google Scholar 

  49. L. Yang, D.R. Powell, R.P. Houser, Dalton Trans. 9, 955 (2007)

    Google Scholar 

  50. A. Okuniewski, D. Rosiak, J. Chojnacki, B. Becker, Polyhedron 90, 47 (2015)

    CAS  Google Scholar 

  51. B. Cordero, V. Gomez, A.E. Platero-Prats, M. Reves, J. Echeverria, E. Cremades, F. Barragan, S. Alvarez, Dalton Trans. 21, 2832 (2008)

    Google Scholar 

  52. N. Kaloğlu, M. Kaloğlu, M.N. Tahir, C. Arıcı, C. Bruneau, H. Doucet, P.H. Dixneuf, B. Çetinkaya, İ Özdemir, J. Organomet. Chem. 867, 404 (2018)

    Google Scholar 

  53. Y. Han, H.V. Huynh, G.K. Tan, Organometallics 26, 6447 (2007)

    CAS  Google Scholar 

  54. H.V. Huynh, W. Sim, C.F. Chin, Dalton Trans. 40, 11690 (2011)

    CAS  PubMed  Google Scholar 

  55. Y.-C. Lin, H.-H. Hsueh, S. Kanne, L.-K. Chang, F.-C. Liu, I.J.B. Lin, G.-H. Lee, S.-M. Peng, Organometallics 32, 3859 (2013)

    CAS  Google Scholar 

  56. L. Barbu, M.M. Popa, S. Shova, M. Ferbinteanu, C. Draghici, F. Dumitrascu, Inorg. Chim. Acta 463, 97 (2017)

    CAS  Google Scholar 

  57. M. Kaloğlu, İ Özdemir, V. Dorcet, C. Bruneau, H. Doucet, Eur. J. Inorg. Chem. 10, 1382 (2017)

    Google Scholar 

  58. M.S. McClure, B. Glover, E. McSorley, E. Millar, M.H. Osterhout, F. Roschangar, Org. Lett. 3, 1677 (2001)

    CAS  PubMed  Google Scholar 

  59. B. Glover, K.A. Harvey, B. Liu, M.J. Sharp, M.F. Tymoschenko, Org. Lett. 5, 301 (2003)

    CAS  PubMed  Google Scholar 

  60. M. Parisien, D. Valette, K. Fagnou, J. Org. Chem. 70, 7578 (2005)

    CAS  PubMed  Google Scholar 

  61. E. David, C. Rangheard, S. Pellet-Rostaing, M. Lemaire, Synlett 13, 2016 (2006)

    Google Scholar 

  62. E. David, S. Pellet-Rostaing, E. Lemaire, Tetrahedron 63, 8999 (2007)

    CAS  Google Scholar 

  63. A. Battace, M. Lemhadri, T. Zair, H. Doucet, M. Santelli, Organometallics 26, 472 (2007)

    CAS  Google Scholar 

  64. H.A. Chiong, O. Daugulis, Org. Lett. 9, 1449 (2007)

    CAS  PubMed  Google Scholar 

  65. A. Battace, M. Lemhadri, T. Zair, H. Doucet, M. Santelli, Adv. Synth. Catal. 349, 2507 (2007)

    CAS  Google Scholar 

  66. P. Amaladass, J.A. Clement, A.K. Mohanakrishnan, Tetrahedron 63, 10363 (2007)

    CAS  Google Scholar 

  67. F. Derridj, A.L. Gottumukkala, S. Djebbar, H. Doucet, Eur. J. Inorg. Chem. 16, 2550 (2008)

    Google Scholar 

  68. F. Pozgan, J. Roger, H. Doucet, Chemsuschem 1, 404 (2008)

    CAS  PubMed  Google Scholar 

  69. J. Roger, F. Pozgan, H. Doucet, Green Chem. 11, 425 (2009)

    CAS  Google Scholar 

  70. M. Kaloğlu, İ Özdemir, Appl. Organometal. Chem. 32, e4399 (2018)

    Google Scholar 

  71. M. Kaloğlu, N. Gürbüz, İ. Yıldırım, N. Özdemir, İ. Özdemir, Appl. Organometal. Chem. 34, e5387 (2020)

    Google Scholar 

  72. X-AREA (Version 1.18) and X-RED32 (Version 1.04), Stoe & Cie, (Darmstadt, Germany, (2002)

  73. L. Palatinus, G. Chapuis, J. Appl. Crystallogr. 40, 786 (2007)

    CAS  Google Scholar 

  74. G.M. Sheldrick, Acta Crystallogr. C71, 3 (2015)

    Google Scholar 

  75. O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann, J. Appl. Crystallogr. 42, 339 (2009)

    CAS  Google Scholar 

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Acknowledgements

This study was supported by the Technological and Scientific Research Council of Turkey TÜBİTAK (Project No: 119R003) and Ondokuz Mayıs University (Project No: PYO.FEN.1906.19.001).

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Authors and Affiliations

  1. Faculty of Science and Arts, Department of Chemistry, İnönü University, 44280, Malatya, Turkey

    Murat Kaloğlu, Nazan Kaloğlu & İsmail Özdemir

  2. Catalysis Research and Application Center, İnönü University, 44280, Malatya, Turkey

    Murat Kaloğlu, Nazan Kaloğlu & İsmail Özdemir

  3. Faculty of Education, Department of Mathematics and Science Education, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Namık Özdemir

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  1. Murat Kaloğlu
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Correspondence to İsmail Özdemir.

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Appendix

Appendix CCDC 2,050,747 for the complex 4d contains the supplementary crystallographic data for the compound reported in this article. These data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [E-mail: deposit@ccdc.cam.ac.uk, https://www.ccdc.cam.ac.uk/structures/].

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Kaloğlu, M., Kaloğlu, N., Özdemir, N. et al. The first use of [PdBr2(imidazolidin-2-ylidene)(pyridine)] catalysts in the direct C-H bond arylation of C2-substituted furan and thiophene. Res Chem Intermed 47, 2821–2843 (2021). https://doi.org/10.1007/s11164-021-04444-4

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