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Mizoroki–Heck coupling: a novel approach for synthesis of (E)-1-(3-argioallyl)indoline-2,3-dione

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Abstract

In the present work, we have performed eco-benign strategy of in situ formation of PdNPs using aqueous extract of Acacia auriculiformis pods for Mizoroki–Heck coupling. A series of (E)-1-(3-argioallyl)indoline-2,3-diones have been synthesized from coupling of aryl halides with allyl isatins. The PdNPs were characterized by transmission electron microscopy (TEM) which revealed PdNPs size of around 6 nm. The key features of the present method are synthesis of novel derivatives of (E)-1-(3-argioallyl)indoline-2,3-diones, PdNPs in aqueous biosurfactant extract as catalytic system which can be recycled for four times without significant loss in the catalytic activity, no need of external ligand. The influence of various parameters such as the nature and amount of base, source of Pd, screening of available surfactants as well as the effect of temperature has been investigated.

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References

  1. Whitcombe NJ, HiiK KM, Gibson SE (2001) Tetrahedron 57:7449

    Article  CAS  Google Scholar 

  2. Farina V (2004) Adv Synth Catal 346:1553

    Article  CAS  Google Scholar 

  3. Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359

    Article  CAS  PubMed  Google Scholar 

  4. Albaneze Walker J, Murry JA, Soheili A, Ceglia S, Springfield SA, Bazaral C, Dormer PG, Hughes DL (2005) Tetrahedron 61:6330

    Article  CAS  Google Scholar 

  5. Kertesz M, Choi CH, Yang S (2005) Chem Rev 105:3448

    Article  CAS  PubMed  Google Scholar 

  6. Simon MO, Li CJ (2012) Chem Soc Rev 41:1415

    Article  CAS  PubMed  Google Scholar 

  7. Anastas P, Eghbali N (2010) Chem Soc Rev 39:301

    Article  CAS  PubMed  Google Scholar 

  8. Carril M, Martin RS, Dominguez E (2008) Chem Soc Rev 37:639

    Article  CAS  PubMed  Google Scholar 

  9. Shaughnessy KH (2006) Eur J Org Chem 2006:1817

    Article  Google Scholar 

  10. DeSimone JM (2002) Science 297:799

    Article  CAS  PubMed  Google Scholar 

  11. Savage PE (1999) Chem Rev 99:603

    Article  CAS  PubMed  Google Scholar 

  12. Gawande MB, Bonifacio VD, Luque R, Branco PS, Varma RS (2013) Chem Soc Rev 42:5522

    Article  CAS  PubMed  Google Scholar 

  13. Nasrollahzadeh M, Sajadi SM, Maham M (2015) J Catal A 396:297

    Article  CAS  Google Scholar 

  14. LaSorella G, Strukul G, Scarso A (2015) Green Chem 17:644

    Article  CAS  Google Scholar 

  15. Khazaei A, Rahmati S, Hekmatian Z, Saeednia S (2013) J Mol Catal A Chem 372:160

    Article  CAS  Google Scholar 

  16. Puthiaraja P, Pitchumani K (2014) Green Chem 16:4223

    Article  Google Scholar 

  17. Phillip J, Anna T, Victor S, Valerie JP (2021) Adv Colloid Interface Sci 288:102340

    Article  Google Scholar 

  18. Chahdoura F, Favier I, Pradel C, Mallet-Ladeira S, Gómez M (2015) Catal Commun 63:47

    Article  CAS  Google Scholar 

  19. Leonie AS, Maria GCS, Italo JBD, Karen GOB, Beatriz GR, Ivison AS, Matthew ST, Ibrahim MB (2022) Biochem Eng J 181:108377

    Article  Google Scholar 

  20. Markandea AR, Patelb D, Varjanic S (2021) Bioresour Technol 330:124963

    Article  Google Scholar 

  21. Patil SP, Jadhav SN, Rode CV, Shejwal RV, Kumbhar AS (2020) Transit Met Chem 45:403

    Article  CAS  Google Scholar 

  22. Han K, Zhou Y, Liu F, Guo Q, Wang P, Yang Y, Song B, Liu W, Yao Q, Teng Y, Yu P (2014) Bioorg Med Chem Lett 24:591

    Article  CAS  PubMed  Google Scholar 

  23. Tarek AF, Bin-Jubair FAS (2010) Int J Res Pharm Sci 1:113

    CAS  Google Scholar 

  24. Matheus ME, Violante FA, Garden SJ, Pinto AC, Fernandes PD (2007) Eur J Pharmacol 556:200

    Article  CAS  PubMed  Google Scholar 

  25. Chohan ZH, Pervez H, Rauf A, Khan KM, Supuran CT (2004) J Enzyme Inhib Med Chem 19:417

    Article  CAS  PubMed  Google Scholar 

  26. Kilpin KJ, Henderson W, Nicholson BK (2007) Polyhedron 26:204

    Article  CAS  Google Scholar 

  27. Verma M, Pandeya SN, Singh KN, Stables JP (2004) Acta Pharm 54:49

    CAS  PubMed  Google Scholar 

  28. Rasmussen HB, MacLeod JK (1997) J Nat Prod 60:1152

    Article  CAS  Google Scholar 

  29. Khokhar S, Feng Y, Campitelli MR, Quinn RJ, Hooper JNA, Ekins MG, Davis RA (2013) J Nat Prod 76:2100

    Article  CAS  PubMed  Google Scholar 

  30. Hughes CC, Fenical W (2010) J Am Chem Soc 132:2528

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. Asati N, Yadava RN (2014) Int J Pharm Res Bio-Sci 3:341

    CAS  Google Scholar 

  32. Mandal P, Sinha Babu SP, Mandal NC (2005) Fitoterapia 76:462

    Article  CAS  PubMed  Google Scholar 

  33. Shmidt MS, Reverdito AM, Kremenchuzky L, Perillo IA, Blanco MM (2008) Molecules 13:831

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Shrestha R, Lee GJ, Lee YR (2016) RSC Adv 6:63782

    Article  CAS  Google Scholar 

  35. Sele AM, Bremner JB, Willis AC, Haritakun R, Griffith R, Keller PA (2015) Tetrahedron 43:8357

    Article  Google Scholar 

  36. Jha M, Shelke GM, Kumar A (2014) Eur J Org Chem 16:3334

    Article  Google Scholar 

  37. Vaidya GN, Nagpure M, Kumar D (2021) ACS Sustain Chem Eng 9:1846

    Article  CAS  Google Scholar 

  38. Jha M, Shelke GM, Kumar A (2014) Eur J Org Chem 2014:3334

    Article  CAS  Google Scholar 

  39. Trost BM, Kalnmals CA, Ramakrishnan D, Ryan MC, Smaha RW, Parkin S (2020) Org Lett 22:2584

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

One of the authors, PMM is grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, Government of India, for the award of the Junior Research Fellowship (File no. 09/ 816(0040)/2017-EMR-I).

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Authors and Affiliations

  1. Department of Chemistry, Shivaji University, Kolhapur, 416004, India

    Mayuri V. Patil, Pradeep M. Mhaldar & Dattaprasad M. Pore

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  1. Mayuri V. Patil
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  2. Pradeep M. Mhaldar
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  3. Dattaprasad M. Pore
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Correspondence to Dattaprasad M. Pore.

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Patil, M.V., Mhaldar, P.M. & Pore, D.M. Mizoroki–Heck coupling: a novel approach for synthesis of (E)-1-(3-argioallyl)indoline-2,3-dione. Monatsh Chem 153, 1243–1250 (2022). https://doi.org/10.1007/s00706-022-02978-w

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