Advertisement

In situ palladium/N-heterocyclic carbene complex catalyzed carbonylative cross-coupling reactions of arylboronic acids with 2-bromopyridine under CO pressure: efficient synthesis of unsymmetrical arylpyridine ketones and their antimicrobial activities

  • L. Boubakri
  • Abdullah S. Al-Ayed
  • L. Mansour
  • A. A. Harrath
  • J. Al-Tamimi
  • I. Özdemir
  • S. Yasar
  • N. HamdiEmail author
Article
  • 60 Downloads

Abstract

The carbonylative Suzuki cross-coupling of 2-bromopyridine with various boronic acids to prepare unsymmetrical arylpyridine ketones has been carried out using palladium/N-heterocyclic carbene complexes as catalysts prepared in situ. The selectivity and the rate of these reactions are highly dependent on the conditions, i.e., nature of the palladium catalyst precursor, solvent, temperature and CO pressure. The main side-products arise from direct, non-carbonylative cross-coupling. Under the optimum conditions, arylpyridine ketones are recovered in high yields (60–88%). The antibacterial activities of the corresponding benzimidazole salts 2 were tested against Gram positive and negative bacteria using the agar dilution procedure, and their IC50 values have been determined.

Notes

Acknowledgements

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for funding this research group No (RG-1435-023).

References

  1. 1.
    Arduengo AJ III, Harlow RL, Kline M (1991) J Am Chem Soc 113:361–363CrossRefGoogle Scholar
  2. 2.
    Herrmann WA, Elison M, Fisher J, Köcher C, Artus GR (1995) Angew Chem Int Ed 34:2371CrossRefGoogle Scholar
  3. 3.
    Scott NM, Nolan SP (2005) Eur J Inorg Chem 2005:1815–1828CrossRefGoogle Scholar
  4. 4.
    Wanzlick HW, Schikora E (1960) Angew Chem 72:494CrossRefGoogle Scholar
  5. 5.
    Ozdemir I, Demir S, Yasar S, Çetinkaya B (2005) Appl Organometal Chem 19:55–58CrossRefGoogle Scholar
  6. 6.
    Ozdemir I, Yasar S, Demir S, Cetinkaya B (2005) Heteroat Chem 16:557–561CrossRefGoogle Scholar
  7. 7.
    Bourissou D, Guerret O, Gabbaï FP, Bertrand G (2000) Chem Rev 100:39CrossRefGoogle Scholar
  8. 8.
    Hermann WA (2002) Angew Chem Int Ed 41:1290CrossRefGoogle Scholar
  9. 9.
    Grasa GA, Viciu MS, Huang J, Zhang C, Trudell ML, Nolan SP (2002) Organometallics 21:2866CrossRefGoogle Scholar
  10. 10.
    Díez-González S, Nolan SP (2007) Coord Chem Rev 251:874CrossRefGoogle Scholar
  11. 11.
    Diez-Gonzalez S, Marion N, Nolan SP (2009) Chem Rev 109:3612–3676CrossRefGoogle Scholar
  12. 12.
    Karaca EÖ, Akkoç M, Öz E, Altin S, Dorcet V, Roisnel T, Gürbüz N, Çelik Ö, Bayri A, Bruneau C, Yaşar S, Özdemir I (2017) J Coord Chem 70:1270–1284CrossRefGoogle Scholar
  13. 13.
    Yasar S, Dogan O, Ozdemir I, Cetinkaya B (2008) Appl Organometal Chem 22:314–318CrossRefGoogle Scholar
  14. 14.
    Boubakri L, Yasar S, Dorcet V, Roisnel T, Bruneau C, Hamdi N, Ozdemir I (2017) New J Chem 41:5105–5113CrossRefGoogle Scholar
  15. 15.
    Herrmann WA, Elison M, Fischer J, Köcher C, Artus GRJ (1995) Angew Chem Int Ed Engl 34:2371–2374CrossRefGoogle Scholar
  16. 16.
    Herrmann WA, Reisinger C-P, Spiegler M (1998) J Organomet Chem 557:93–96CrossRefGoogle Scholar
  17. 17.
    Herrmann WA, Böhm VPW, Gstöttmayr CWK, Grosche M, Reisinger C-P, Weskamp T (2001) J Organomet Chem 617–618:616–628CrossRefGoogle Scholar
  18. 18.
    Hillier AC, Grasa GA, Viciu MS, Lee HM, Yang C, Nolan SP (2002) J Organomet Chem 653:69–82CrossRefGoogle Scholar
  19. 19.
    Ohta H, Fujihara T, Tsuji Y (2008) Dalton Trans 3:379–385CrossRefGoogle Scholar
  20. 20.
    Gstöttmayr CWK, Böhm VPW, Herdtweck E, Grosche M, Herrmann WA (2002) Angew Chem Int Ed 41:1363–1365CrossRefGoogle Scholar
  21. 21.
    Viciu MS, Kissling RM, Stevens ED, Nolan SP (2002) Org Lett 4:2229–2231CrossRefGoogle Scholar
  22. 22.
    Viciu MS, Germaneau RF, Nolan SP (2002) Org Lett 4:4053–4056CrossRefGoogle Scholar
  23. 23.
    Viciu MS, Germaneau RF, Navarro-Fernandez O, Stevens ED, Nolan SP (2002) Organometallics 21:5470–5472CrossRefGoogle Scholar
  24. 24.
    Altenhoff G, Goddard R, Lehmann CW, Glorius F (2003) Angew Chem Int Ed 42:3690–3693CrossRefGoogle Scholar
  25. 25.
    O’Brien CJ, Kantchev EAB, Valente C, Hadei N, Chass GA, Lough A, Hopkinson AC, Organ MG (2006) Chem-Eur J 12:4743–4748CrossRefGoogle Scholar
  26. 26.
    Nun P, Martinez J, Lamaty F (2009) Synlett 2009:1761–1764CrossRefGoogle Scholar
  27. 27.
    Fürstner A, Seidel G, Kremzow D, Lehmann CW (2003) Organometallics 22:907–909CrossRefGoogle Scholar
  28. 28.
    Navarro O, Kaur H, Mahjoor P, Nolan SP (2004) J Org Chem 69:3173–3180CrossRefGoogle Scholar
  29. 29.
    Han Y, Huynh HV, Tan GK (2007) Organometallics 26:6447CrossRefGoogle Scholar
  30. 30.
    Yen SK, Koh LL, Huynh HV, Hor TSA (2008) Chem Asian J 3:1649CrossRefGoogle Scholar
  31. 31.
    Yuan D, Huynh HV (2010) Organometallics 29:6020CrossRefGoogle Scholar
  32. 32.
    Shang N, Gao S, Feng C, Zhang H, Wang C, Wang Z (2013) RSC Adv 3:21863–21868CrossRefGoogle Scholar
  33. 33.
    Shang N, Feng C, Zhang H, Gao S, Tang R, Wang C, Wang Z (2013) Catal Commun 40:111–115CrossRefGoogle Scholar
  34. 34.
    Zhang L, Feng C, Gao S, Wang Z, Wang C (2015) Catal Commun 61:21–25CrossRefGoogle Scholar
  35. 35.
    Huang Y, Zheng Z, Liu T, Lü J, Lin Z, Li H, Cao R (2011) Catal Commun 14:27–31CrossRefGoogle Scholar
  36. 36.
    Roughley SD, Jordan AM (2011) J Med Chem 54:3451CrossRefGoogle Scholar
  37. 37.
    Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581CrossRefGoogle Scholar
  38. 38.
    Heck RF, Jr JP (1972) Nolley. J Org Chem 37:2320–2322CrossRefGoogle Scholar
  39. 39.
    Miyaura N, Yanagi T, Suzuki A (1981) Synth Commun 11:513–519CrossRefGoogle Scholar
  40. 40.
    Mohanty S, Suresh D, Balakrishna MS, Mague JT (2008) Tetrahedron 64:240–247CrossRefGoogle Scholar
  41. 41.
    Yates FS (1984) In: Boulton AJ, Mckillop A (eds) Comprehensive heterocyclic chemistry, vol 2, chapter 2.08. Pergamon, OxfordGoogle Scholar
  42. 42.
    Balasubramanian M, Keay JG (1995) In: Mckillop A (ed) Comprehensive heterocyclic chemistry II, vol 5, chapter 5.06. Pergamon, OxfordGoogle Scholar
  43. 43.
    Hlasta DJ, Court JJ (1989) Tetrahedron Lett 30:1773–1776CrossRefGoogle Scholar
  44. 44.
    Gros P, Fort Y, Caubère P (1997) J Chem Soc Perkin Trans 1:3597–3600CrossRefGoogle Scholar
  45. 45.
    Furukawa N, Shibutani T, Matsumura K, Fujihara H (1986) Tetrahedron Lett 27:3899–3902CrossRefGoogle Scholar
  46. 46.
    Trecourt F, Breton G, Bonnett V, Mongin F, Marsais F, Queguiner G (1999) Tetrahedron Lett 40:4339–4342CrossRefGoogle Scholar
  47. 47.
    Kondo Y, Shilai M, Uchiyama M, Sakamoto T (1996) J Chem Soc Perkin Trans 1:1781–1782CrossRefGoogle Scholar
  48. 48.
    Sakamoto T, Kondo Y, Murata N, Yamanaka H (1992) Tetrahedron Lett 33:5373–5374CrossRefGoogle Scholar
  49. 49.
    Sakamoto T, Kondo Y, Murata N, Yamanaka H (1993) Tetrahedron 49:9713–9720CrossRefGoogle Scholar
  50. 50.
    Yamamoto Y, Yanagi A (1982) Chem Pharm Bull 30:2003–2010CrossRefGoogle Scholar
  51. 51.
    Yamamoto Y, Ouchi H, Tanaka T (1995) Chem Pharm Bull 43:1028–1030CrossRefGoogle Scholar
  52. 52.
    Choudary BM, Bhuma V, Narender N (1996) Ind J Chem Sect B 35B:281–282Google Scholar
  53. 53.
    Mohammadpoor-Baltork I, Sadeghi MM, Mahmoodi N, Kharamesh B (1997) Ind J Chem Sect B 36B:438–441Google Scholar
  54. 54.
    Mohammad-Baltork I, Hajipour AR, Mohammadi H (1998) Bull Chem Soc Jpn 71:1649–1653CrossRefGoogle Scholar
  55. 55.
    Hajipour AR, Mahboobkhak N (1998) Ind J Chem Sect B 37B:285–287Google Scholar
  56. 56.
    Hajipour AR, Mohammadpoor-Baltork I, Kianfar G (1998) Bull Chem Soc Jpn 71:2655–2659CrossRefGoogle Scholar
  57. 57.
    Hajipour AR, Mahboobkhak N (1998) Synth Commun 28:3143–3150CrossRefGoogle Scholar
  58. 58.
    Herrmann CKF, Sachdeva YP, Wolfe JF (1987) J Heterocycl Chem 24:1061–1065CrossRefGoogle Scholar
  59. 59.
    De Kimpe R, Keppens M, Fonck G (1996) Chem Commun 5:635–636CrossRefGoogle Scholar
  60. 60.
    Ishiyama T, Kizaki H, Miyaura N, Suzuki A (1993) Tetrahedron Lett 34:7595–7598CrossRefGoogle Scholar
  61. 61.
    Ishiyama T, Kizaki H, Hayashi T, Suzuki A, Miyaura N (1998) J Org Chem 63:4726–4731CrossRefGoogle Scholar
  62. 62.
    Couve-Bonnaire S, Carpentier J-F, Mortreux A, Castanet Y (2001) Tetrahedron Lett 42:3689–3691CrossRefGoogle Scholar
  63. 63.
    Liu Y, Ye K, Fan Y, Song W, Wang Y, Hou Z (2009) Chem Commun 25:3699–3701CrossRefGoogle Scholar
  64. 64.
    Pefkianakis EK, Tzanetos NP, Kallitsis JK (2008) Chem Mater 20:6254CrossRefGoogle Scholar
  65. 65.
    Thomas SW, Venkatesan K, Müller P, Swager TM (2006) J Am Chem Soc 128:16641CrossRefGoogle Scholar
  66. 66.
    Miyaura N, Suzuki A (1995) Chem Rev 95:2457CrossRefGoogle Scholar
  67. 67.
    Billingsley K, Buchwald SL (2008) Angew Chem Int Ed 47:4695CrossRefGoogle Scholar
  68. 68.
    Yamamoto Y, Takizawa M, Yu X, Miyaura N (2008) Angew Chem Int Ed 47:928CrossRefGoogle Scholar
  69. 69.
    Billingsley K, Buchwald SL (2007) J Am Chem Soc 129:3358CrossRefGoogle Scholar
  70. 70.
    Hodgson PB, Salingue FH (2004) Tetrahedron Lett 45:685CrossRefGoogle Scholar
  71. 71.
    Gros P, Doudouh A, Fort Y (2004) Tetrahedron Lett 45:6239CrossRefGoogle Scholar
  72. 72.
    Deng JZ, Paone DV, Ginnetti AT, Kurihara H, Dreher SD, Weissman SA, Stauffer SR, Burgey CS (2009) Org Lett 11:345CrossRefGoogle Scholar
  73. 73.
    Yang DX, Colletti SL, Wu K, Song M, Li GY, Shen HC (2009) Org Lett 11:381CrossRefGoogle Scholar
  74. 74.
    Billingsley KL, Anderson KW, Buchwald SL (2006) Angew Chem Int Ed 45:3484CrossRefGoogle Scholar
  75. 75.
    Kudo N, Perseghini M, Fu GC (2006) Angew Chem Int Ed 45:1282CrossRefGoogle Scholar
  76. 76.
    Fleckenstein CA, Plenio H (2008) J Org Chem 73:3236CrossRefGoogle Scholar
  77. 77.
    Fleckenstein CA, Plenio H (2007) Green Chem 9:1287CrossRefGoogle Scholar
  78. 78.
    Clapham KM, Batsanov AS, Bryce MR, Tarbit B (2009) Org Biomol Chem 7:2155CrossRefGoogle Scholar
  79. 79.
    Dong C-G, Liu T-P, Hu Q-S (2009) Synlett 7:1081Google Scholar
  80. 80.
    Kondolff I, Doucet H, Santelli M (2007) J Mol Catal A: Chem 269:110CrossRefGoogle Scholar
  81. 81.
    Touj N, Al-Ayed AS, Sauthier M, Mansour L, Harrath AH, Al-Tamimi J, Özdemir I, Yaşard S, Hamdi N (2018) RSC Adv 8:40000–40015CrossRefGoogle Scholar
  82. 82.
    Boubakri L, Mansour L, Harrath AH, Özdemir I, Yaşar S, Hamdi N (2018) J Coord Chem 71:133–189CrossRefGoogle Scholar
  83. 83.
    Salman AW, Haque RA, Budagumpi S, Zulikha HZ (2013) Polyhedron 49:200CrossRefGoogle Scholar
  84. 84.
    Yasar S, Özdemir İ, Cetinkaya B, Renaud J-L, Bruneau C (2008) Eur J Org Chem 2008:2142–2149CrossRefGoogle Scholar
  85. 85.
    Maerten E, Sauthier M, Mortreux A, Castanet Y (2007) Tetrahedron 63:682–689CrossRefGoogle Scholar
  86. 86.
    Güven K, Yücel E, Cetintas F (2006) Pharm. Biol. 44:79–83CrossRefGoogle Scholar
  87. 87.
    National Committee for Clinical Laboratory Standard (1998) In: Proposed standard M38-P. National Committee for Clinical Laboratory Standard, WayneGoogle Scholar

Copyright information

© Springer Nature Switzerland AG 2018

Authors and Affiliations

  1. 1.Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and TechnologyUniversity of CarthageHammam-LifTunisia
  2. 2.Chemistry Department, College of Science and ArtsQassim UniversityAl-RassSaudi Arabia
  3. 3.Zoology Department, College of ScienceKing Saud UniversityRiyadhSaudi Arabia
  4. 4.Department of Chemistry, Faculty of Science and Artİnönü UniversityMalatyaTurkey

Personalised recommendations