Skip to main content
Log in

Application of Biosynthesized CuO Nanoparticles Using Rosa canina Fruit Extract as a Recyclable and Heterogeneous Nanocatalyst for Alkyne/Aldehyde/Amine A3 Coupling Reactions

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Copper oxide (CuO) nanoparticles (NPs) were prepared through a biological procedure where the Rosa canina fruit extract was used as a capper and reductant agent. For the three-component reaction of amines, aldehydes and alkynes (A3 coupling), these CuO NPs were used as an effective heterogeneous nanocatalyst. Various propargylamines were obtained in a good yield. Additionally, the reuse and separation of CuO NPs was extremely effective, economical and simple.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Fig. 2

Similar content being viewed by others

References

  1. Liu Y (2014) ARKIVOC 1:1

    Google Scholar 

  2. Vessally E (2016) RSC Adv 6:18619

    Article  CAS  Google Scholar 

  3. Matsuda I, Sakakibara J, Nagashima H (1991) Tetrahedron Lett 32:7431

    Article  CAS  Google Scholar 

  4. Yu PH, Davis BA, Boulton AA (1992) J Med Chem 35:3705

    Article  CAS  PubMed  Google Scholar 

  5. Chen JJ, Swope DM, Dashtipour K (2007) Clin Ther 29:1825

    Article  CAS  PubMed  Google Scholar 

  6. Magueur G, Crousse B, Bonnet-Delpon D (2005) Tetrahedron Lett 46:2219

    Article  CAS  Google Scholar 

  7. Kaur P, Shakya G, Sun H, Pan Y, Li G (2010) Org Biomol Chem 8:1091

    Article  CAS  PubMed  Google Scholar 

  8. Wei C, Li C-J (2002) J Am Chem Soc 124:5638

    Article  CAS  PubMed  Google Scholar 

  9. Herrera RP (2015) Marques-Lopez E Multicomponent Reactions: Concepts and Applications for Design and Synthesis. Wiley, Hoboken, p 94

    Google Scholar 

  10. Peshkov VA, Pereshivko OP, Van der Eycken EV (2012) Chem Soc Rev 41:3790

    Article  CAS  PubMed  Google Scholar 

  11. Akullian LC, Snapper ML, Hoveyda AH (2003) Angew Chem Int Ed 42:4244

    Article  CAS  Google Scholar 

  12. Afraj SN, Chen C, Lee GH (2014) RSC Adv 4:26301

    Article  CAS  Google Scholar 

  13. Kuninobu Y, Inoue Y, Takai K (2006) Chem Lett 35:1376

    Article  CAS  Google Scholar 

  14. Kotadia DA, Soni SS (2014) Appl Catal A 488:231

    Article  CAS  Google Scholar 

  15. Zeng T, Chen WW, Cirtiu CM, Moores A, Song G, Li CJ (2010) Green Chem 12:570

    Article  CAS  Google Scholar 

  16. Li C-J, Wei C (2002) Chem Commun 3:268

    Article  CAS  Google Scholar 

  17. Bonfield ER (2007) Org Biomol Chem 5:435

    Article  CAS  PubMed  Google Scholar 

  18. Chen WW, Bi HP, Li CJ (2010) Synlett 2010:475–479

    Article  CAS  Google Scholar 

  19. Sakaguchi S, Kubo T, Ishii Y (2001) Angew Chem Int Ed 40:2534

    Article  CAS  Google Scholar 

  20. Fischer C, Carreira EM (2001) Org Lett 3:4319

    Article  CAS  PubMed  Google Scholar 

  21. Samai S, Nandi GC, Singh M (2010) Tetrahedron Lett 51:5555

    Article  CAS  Google Scholar 

  22. Namitharan K, Pitchumani K (2010) Eur J Org Chem 2010:411–415

    Article  CAS  Google Scholar 

  23. Manikandana R, Anithaa P, Viswanathamurthia P, Malecki JG (2016) Polyhedron 119:300

    Article  CAS  Google Scholar 

  24. Cheng S, Shang N, Feng C, Gao S, Wang C, Wang Z (2017) Catal Commun 89:91

    Article  CAS  Google Scholar 

  25. Varyani M, Khatri PK, Jain SL (2016) Catal Commun 77:113

    Article  CAS  Google Scholar 

  26. Islam MM, Roy AS, Islam SM (2016) Cat Lett 146:1128

    Article  CAS  Google Scholar 

  27. Naeimi H, Moradian M (2013) Appl Catal A 467:400

    Article  CAS  Google Scholar 

  28. Wang M, Li P, Wang L (2008) Eur J Org Chem 2008:2255–2261

    Article  CAS  Google Scholar 

  29. Wei C, Li Z, Li C-J (2003) Org Lett 5:4473

    Article  CAS  PubMed  Google Scholar 

  30. Li P, Wang L, Zhang Y, Wang M (2008) Tetrahedron Lett 49:6650

    Article  CAS  Google Scholar 

  31. Li Y, Chan X, Song Y, Fang L, Zou G (2011) Dalton Trans 40:2046

    Article  CAS  PubMed  Google Scholar 

  32. Gholinejad M, Hamed F, Nájera C (2016) Synlett 27:1193

    Article  CAS  Google Scholar 

  33. Veisi H, Farokhi M, Hamelian M, Hemmati S (2018) RSC Adv 8:38186

    Article  CAS  Google Scholar 

  34. Wei C, Li C-J (2003) J Am Chem Soc 125:9584

    Article  CAS  PubMed  Google Scholar 

  35. Kidwai M, Bansal V, Kumarb A, Mozumdarb S (2007) Green Chem 9:742

    Article  CAS  Google Scholar 

  36. Qiu Y, Qin Y, Ma Z, Xia W (2014) Chem Lett 43:1284

    Article  CAS  Google Scholar 

  37. Eagalapatia NP, Rajacka A, Murthy YLN (2014) J Mol Catal A: Chem 381:126

    Article  CAS  Google Scholar 

  38. Raghuvanshi DS, Singh KN (2011) Synlett 2011:373–377

    Article  CAS  Google Scholar 

  39. Li PH, Wang L (2005) Chin J Chem 23:1076

    Article  CAS  Google Scholar 

  40. Astruc D (2008) Nanoparticles and catalysis. Wiley-VCH, Weinheim

    Google Scholar 

  41. Polshettiwar V, Varma RS (2010) Green Chem 12:743

    Article  CAS  Google Scholar 

  42. Veisi H, Razeghi S, Mohammadi P, Hemmati S (2019) Mat Sci Eng C 97:624

    Article  CAS  Google Scholar 

  43. Veisi H, Moradi SB, Saljooqi A, Safarimehr P (2019) Mat Sci Eng C 100:445

    Article  CAS  Google Scholar 

  44. Veisi H, Ghorbani M, Hemmati S (2019) Mat Sci Eng C 98:584

    Article  CAS  Google Scholar 

  45. Veisi H, Safarimehr P, Hemmati S (2019) Mat Sci Eng C 96:310

    Article  CAS  Google Scholar 

  46. Sreedhar B, Kumar AS, Reddy PS (2009) Tetrahedron Lett 50:2322

    Article  CAS  Google Scholar 

  47. Zeng TQ, Chen WW, Cirtiu CM, Moores A, Song G, Li CJ (2010) Green Chem 12:5701

    Article  CAS  Google Scholar 

  48. Das D (2016) ChemistrySelect 1:1959

    Article  CAS  Google Scholar 

  49. Li Q, Xu J, Zhang J, Pang H (2018) ChemistrySelect 3:12206

    Google Scholar 

  50. Veisi H, Hemmati S, Javaheri H (2017) Tetrahedron Lett 58:3155

    Article  CAS  Google Scholar 

  51. Borkow G, Zatcoff RC, Gavia J (2009) Med Hypotheses 73:1–4

    Article  CAS  Google Scholar 

  52. Borkow G, Gabbay J (2009) Curr Chem Biol 3:272

    CAS  Google Scholar 

  53. Kumar RV, Elgamiel RE, Diamant Y, Gedanken A (2001) Langmuir 17:1406

    Article  CAS  Google Scholar 

  54. Wang H, Xu JZ, Zhu JJ, Chen HYJ (2002) Cryst Growth 244:88

    Article  CAS  Google Scholar 

  55. Carnes CL, Stipp J, Klabunde KJ (2002) Langmuir 18:1352

    Article  CAS  Google Scholar 

  56. Zhang Q, Li Y, Xu D, Gu Z (2001) J Mater Sci Lett 20:925

    Article  CAS  Google Scholar 

  57. Xu JF, Ji W, Shen ZX, Tang SH, Ye XR, Jia DZ, Xin XQ (2000) J Solid State Chem 147:516

    Article  CAS  Google Scholar 

  58. Yia AJ, Li J, Jian W, Bennett J, Xu JH (2001) Appl Phys Lett 79:1039

    Article  CAS  Google Scholar 

  59. Fan H, Yang L, Hua W, Wu X, Wu Z, Xie S, Zou B (2004) Nanotechnology 15:37

    Article  CAS  Google Scholar 

  60. Xu CK, Liu YK, Xu GD, Wang GH (2002) Mater Res Bull 37:2365

    Article  CAS  Google Scholar 

  61. Bonyasi F, Hekmati M, Veisi H (2017) J Colloid Interface Sci 496:177

    Article  CAS  PubMed  Google Scholar 

  62. Veisi H, Sedrpoushan A, Maleki B, Hekmati M, Heidari M, Hemmati S (2015) Appl Organomet Chem 29:834

    Article  CAS  Google Scholar 

  63. Veisi H, Hekmati M, Hemmati S (2017) J Heterocycl Chem 54:1630

    Article  CAS  Google Scholar 

  64. Lebaschi S, Hekmati M, Veisi H (2017) J Colloid Interface Sci 485:223

    Article  CAS  PubMed  Google Scholar 

  65. Heidari F, Hekmati M, Veisi H (2017) J Colloid Interface Sci 501:175

    Article  CAS  PubMed  Google Scholar 

  66. Taheri S, Veisi H, Hekmati M (2017) New J Chem 41:5075

    Article  CAS  Google Scholar 

  67. Shahriary M, Veisi H, Hekmati M, Hemmati S (2018) Mat Sci Eng C 90:57

    Article  CAS  Google Scholar 

  68. Hemmati S, Safarimehr P, Hekmati M, Veisi H (2017) J Heterocycl Chem 54:1640

    Article  CAS  Google Scholar 

  69. Shaham G, Veisi H, Hekmati M (2017) Appl Organomet Chem 31:e3737

    Article  CAS  Google Scholar 

  70. Mirfakhrae S, Hekmati M, Hosseini Eshbala F, Veisi H (2018) New J Chem 42:1757

    Article  Google Scholar 

  71. Veisi H, Metghalchi Y, Hekmati M, Samadzadeh S (2017) Appl Organomet Chem 31:e3676

    Article  CAS  Google Scholar 

  72. Akhavan E, Hemmati S, Hekmati M, Veisi H (2018) New Chem 42:2782

    Article  CAS  Google Scholar 

  73. Veisi H, Kavian M, Hekmati M, Hemmati S (2019) Polyhedron 161:338

    Article  CAS  Google Scholar 

  74. Hemmati S, Mehrazin L, Hekmati M, Izadi M, Veisi H (2018) Mat Chem Phys 214:527

    Article  CAS  Google Scholar 

  75. Xiong X, Chen H, Zhu R (2014) Chin J Catal 35:2006

    Article  CAS  Google Scholar 

  76. Wei C, Li Z, Li C-J (2003) Org Lett 5:4473

    Article  CAS  PubMed  Google Scholar 

  77. Srinivasa M, Srinivasua P, Bhargava SK, Lakshmi Kantam M (2013) Catal Today 208:66

    Article  CAS  Google Scholar 

  78. Karimi B, Gholinejad M, Khorasani M (2012) Chem Commun 48:8961

    Article  CAS  Google Scholar 

  79. Chen W-W, Nguyen RV, Li C-J (2009) Tetrahedron Lett 50:2895

    Article  CAS  Google Scholar 

  80. Yan W, Wang R, Xua Z, Xu J, Lin L, Shen Z, Zhou Y (2006) J Mol Catal A 255:81

    Article  CAS  Google Scholar 

  81. Bhatte KD, Sawant DN, Deshmukh KM, Bhanage BM (2011) Catal Commun 16:114

    Article  CAS  Google Scholar 

  82. Sreedhar B, Kumar AS, Reddy PS (2010) Tetrahedron Lett 51:1891

    Article  CAS  Google Scholar 

  83. Lakshmi Kantam M, Laha S, Yadav J, Bhargava S (2008) Tetrahedron Lett 49:3083

    Article  CAS  Google Scholar 

  84. Samai S, Nandi GC, Singh MS (2010) Tetrahedron Lett 51:5555

    Article  CAS  Google Scholar 

  85. Maggi R, Bello A, Oro C, Sartori G, Soldi L (2008) Tetrahedron 64:1435

    Article  CAS  Google Scholar 

  86. Zohreh NS, Hosseini H, Jahani M, Xaba MS, Meijboom R (2017) J Catal 356:255

    Article  CAS  Google Scholar 

  87. Cammarata JR, Rivera R, Fuentes F, Otero Y, Ocando-Mavárez E, Arce A, Garcia JM (2017) Tetrahedron Lett 58:4078

    Article  CAS  Google Scholar 

  88. Yadav JS, Subba Reddy BV, Hara Gopal AV, Patil KS (2009) Tetrahedron Lett 50:3493

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are thankful to Department of Organic Chemistry, Faculty of Pharmaceutical Chemistry, Tehran Medical Sciences, Islamic Azad University, Tehran, Iran for financial supports.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Malak Hekmati.

Additional information

Publisher's Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hekmati, M. Application of Biosynthesized CuO Nanoparticles Using Rosa canina Fruit Extract as a Recyclable and Heterogeneous Nanocatalyst for Alkyne/Aldehyde/Amine A3 Coupling Reactions. Catal Lett 149, 2325–2331 (2019). https://doi.org/10.1007/s10562-019-02833-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-019-02833-4

Keywords

Navigation