Skip to main content
SpringerLink
Log in

Palladium(II) Pincer Type Complexes Containing ONO Donor Heterocyclic Hydrazones: Synthesis, Structure and Catalytic Activity Towards the Suzuki–Miyaura Cross-Coupling of 3-Bromochromone and Arylboronic Acids via C–Br Activation

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Three new pincer type palladium(II) complexes 1–3 synthesized by reacting palladium precursor [PdCl2(PPh3)2] with ONO heterocyclic hydrazone ligands H2L1-3 in equimolar quantities were well characterized using single-crystal XRD, analytical and spectroscopic data. These complexes were examined as homogeneous catalysts for the Suzuki–Miyaura cross-coupling of 3-bromochromone with a range of arylboronic acids in ethanol medium. Catalytic transformations progressed smoothly under aerobic conditions with 0.01 mol% of catalyst load at room temperature to afford an array of 3-arylated chromones (6a–o). This catalyst was reused up to five cycles and favourably this protocol does not require any external oxidant, additives and phase transfer reagents.

Graphical 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
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. Silva CFM, Batista VF, Pinto DCGA, Silva AMS (2018) Expert Opin Drug Dis 13:795–798

    CAS  Google Scholar 

  2. Veitch NC (2007) Nat Prod Rep 24:417–464

    PubMed  CAS  Google Scholar 

  3. Boland GM, Donnelly DMX (1998) Nat Prod Rep 15:241–260

    CAS  Google Scholar 

  4. Ha H, Lee YS, Lee JH (2006) Arch Pharm Res 29:96–101

    PubMed  CAS  Google Scholar 

  5. Van Erp-Baart M-AJ, Brants HAM, Kiely M (2003) Br J Nutr 89:S25–S30

  6. Ding K, Wang S (2005) Tetrahedron Lett 46:3707–3709

    CAS  Google Scholar 

  7. Zhang YC, Albrecht D, Bomser J (2003) J Agr Food Chem 51:7611–7616

    CAS  Google Scholar 

  8. Hendrich S (2002) J Chromatogr B 777:203–210

    CAS  Google Scholar 

  9. Awoniyi CA, Roberts D, Rao Veeramachaneni DN (1998) Fertil Steril 70:440–447

    PubMed  CAS  Google Scholar 

  10. Křížová L, Dadáková K, Kašparovská J, Kašparovský T (2019) Molecules 24:1076

    PubMed  PubMed Central  Google Scholar 

  11. Beggs CJ, Stolzer-Jehle A, Wellmann E (1985) Plant Physiol 79:630–634

    PubMed  PubMed Central  CAS  Google Scholar 

  12. Samanta Amalesh, Das Gouranga DSK (2011) Int J Pharm Sci Tech 6:12–35

  13. Miadoková E (2009) Interdiscip Toxicol 2:211–218

    PubMed  PubMed Central  Google Scholar 

  14. Morel C, Stermitz FR, Tegos G, Lewis K (2003) J Agr Food Chem 51:5677–5679

    CAS  Google Scholar 

  15. Alesawy MS, Abdallah AE, Taghour MS (2021) Molecules 26:2806

    PubMed  PubMed Central  CAS  Google Scholar 

  16. Lee JH, Renita M, Fioritto RJ (2004) J Agric Food Chem 52:2647–2651

    PubMed  CAS  Google Scholar 

  17. Barve V, Ahmed F, Adsule S (2006) J Med Chem 49:3800–3808

    PubMed  CAS  Google Scholar 

  18. Yu J, Bi X, Yu B, Chen D (2016) Nutrients 8:1–16

    Google Scholar 

  19. Toukam PD, Tagatsing MF, Tchokouaha Yamthe LR et al (2018) Phytochem Lett 28:69–75

    CAS  Google Scholar 

  20. Shah SK, Jhade DN (2016) Int J Green Pharm 10:S204–S210

    CAS  Google Scholar 

  21. Soni P, Choudhary R, Bodakhe SH (2019) J Integr Med 17:374–382

    PubMed  Google Scholar 

  22. Zhao J, Cheng YY, Fan W et al (2015) CNS Neurosci Ther 21:61–70

    PubMed  CAS  Google Scholar 

  23. Wu Q, Wang M, Sciarappa WJ, Simon JE (2004) J Agr Food Chem 52:2763–2769

    CAS  Google Scholar 

  24. Chen J, Wu Y, Yang C et al (2017) Food and Funct 8:4414–4420

    CAS  Google Scholar 

  25. Hikal WM, Baeshen RS, Said-Al Ahl HAH (2017) Cogent Biol 3:1404274

    Google Scholar 

  26. Cao H, Ou J, Chen L et al (2019) Crit Rev Food Sci Nutr 59:3371–3379

    PubMed  CAS  Google Scholar 

  27. Li W, Liu F, Zhang P (2008). J Chem Res. https://doi.org/10.3184/030823408X382135

    Article  Google Scholar 

  28. Chien JT, Hsieh HC, Kao TH, Chen BH (2005) Food Chem 91:425–434

    CAS  Google Scholar 

  29. Marais JPJ, Ferreira D, Slade D (2005) Phytochem 66:2145–2176

    CAS  Google Scholar 

  30. Paquette LA, Stucki H (1966) J Org Chem 31:1232–1235

    CAS  Google Scholar 

  31. Tsoi YT, Zhou Z, Chan ASC, Yu WY (2010) Org Lett 12:4506–4509

    PubMed  CAS  Google Scholar 

  32. Boström J, Brown DG, Young RJ, Keserü GM (2018) Nat Rev Drug Discov 17:709–727

    PubMed  Google Scholar 

  33. Polshettiwar V, Decottignies A, Len C, Fihri A (2010) Chemsuschem 3:502–522

    PubMed  CAS  Google Scholar 

  34. Astruc D (2011) Anal Bioanal Chem 399:1811–1814

    PubMed  CAS  Google Scholar 

  35. Van Koten G (2013) Top Organomet Chem 40:1–20

    Google Scholar 

  36. Yukio hoshino N miyaura and A suzuki (1988) Bull Chem Sco Jpn. 3008–3010

  37. Wan JP, Tu Z, Wang Y (2019) Chem Eur J 25:6907–6910

    PubMed  CAS  Google Scholar 

  38. Silva VLM, Soengas RG, Silva AMS (2020) Molecules 25(7):1564

    PubMed  PubMed Central  CAS  Google Scholar 

  39. Chang YT, Liu LJ, Peng WS (2021) J Chin Chem Soc 68:469–475

    CAS  Google Scholar 

  40. Firinci E, Firinci R, Sevincek R (2022) J Organomet Chem 978:122471

    CAS  Google Scholar 

  41. Layek S, Agrahari B, Ganguly R (2020) Applied Organomet Chem 34:1–14

    Google Scholar 

  42. Vignesh A, Shalini C, Dharmaraj N (2019) Eur J Inorg Chem 2019:3869–3882

    CAS  Google Scholar 

  43. Vogel AI (1989) Textbook of practical organic chemistry, 5th edn. Longman, London

    Google Scholar 

  44. Sathyadevi P, Krishnamoorthy P, Butorac RR, Cowley AH, Bhuvanesh NSP, Dharmarai N, Dalton Trans (2011) 9690.

  45. APEX3 Program for data collection on area detectors. BRUKER AXS Inc., Madison

  46. SADABS, Sheldrick GM. Program for Absorption Correction of Area Detector Frames. BRUKER AXS Inc., Madison

  47. Sheldrick GM (2008) Acta Cryst A 64:112–122. Sheldrick GM (2015) Acta Cryst A 71:3–8. Sheldrick GM (2015) Acta Cryst C 71:3–8. XT, XS, BRUKER AXS Inc., Madison

  48. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) OLEX2: a complete structure solution, refinement and analysis program. J Appl Cryst 42:339–341

    CAS  Google Scholar 

  49. Spek AL (2003) J Appl Cryst 36:7–13; Spek AL (2008) Utrecht University, Utrecht

  50. Felpin FX, Lory C, Sow H, Acherar S (2007) Tetrahedron 63:3010–3016

    CAS  Google Scholar 

  51. Zhang Z, Qiao J, Wang D (2014) Mol Divers 18:245–251

    PubMed  CAS  Google Scholar 

  52. Babu GN, Pal S (2016) J Organomet Chem 9:805

    Google Scholar 

  53. Rao ARB, Pal S (2012) J Organomet Chem 67:701

    Google Scholar 

  54. Rao ARB, Pal S (2013) J Organomet Chem 67:731

    Google Scholar 

  55. Anitha P, Manikandan R, Viswanathamurthi P (2015) J Coord Chem 68:3537

    CAS  Google Scholar 

  56. Tamizh MM, Karvembu R (2012) Inorg Chem Commun 25:30

    CAS  Google Scholar 

  57. Ayyannan G, Veerasamy P, Mohanraj M, Raja G, Manimaran A, Velusamy M, Bhuvanesh N, Nandhakumar R, Jayabalakrishnan C (2017) Appl Organomet Chem 31:1

    Google Scholar 

  58. Albert J, Gonzalez A, Granell J, Moragas R, Puerta C, Valerga P (1997) Organometallics 16:3775

    CAS  Google Scholar 

  59. Das S, Pal S (2006) J Organomet Chem 691:2575–2583

    CAS  Google Scholar 

  60. Nava DR, Hernández AÁ, Rheingold AL, Suarez-Castillo OR, Mendoza- Espinosa D (2019) Dalton Trans 48:3214–3222

    Google Scholar 

  61. Martin AR, Yang Y (1993) Acta Chem Scand 47:221–230

    CAS  Google Scholar 

Download references

Acknowledgements

Mrs. C. Shalini thanks the Department of Science and Technology (DST), New Delhi, India, for the award of Promotion of University Research and Scientific Excellence (PURSE) – Phase – II fellowship (Official memorandum Number: BU/DST PURSE (II)/Appointment/13).

Author information

Authors and Affiliations

  1. Department of Chemistry, Bharathiar University, Coimbatore, 46, India

    C. Shalini, N. Dharmaraj & M. V. Kaveri

  2. Department of Chemistry, Texas A&M University, College Station, TX, 77842, USA

    Nattamai S. P. Bhuvanesh

Authors
  1. C. Shalini
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. Dharmaraj
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nattamai S. P. Bhuvanesh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. V. Kaveri
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to N. Dharmaraj or M. V. Kaveri.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 858 kb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shalini, C., Dharmaraj, N., Bhuvanesh, N.S.P. et al. Palladium(II) Pincer Type Complexes Containing ONO Donor Heterocyclic Hydrazones: Synthesis, Structure and Catalytic Activity Towards the Suzuki–Miyaura Cross-Coupling of 3-Bromochromone and Arylboronic Acids via C–Br Activation. Catal Lett 154, 132–143 (2024). https://doi.org/10.1007/s10562-023-04276-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-023-04276-4

Keywords

Search

Navigation