[Zn(l-proline)2] Catalyzed One-Pot Synthesis of Propargylamines Under Solvent-Free Conditions

  • Samaresh Layek
  • Bhumika Agrahari
  • Shweta Kumari
  • Anuradha
  • Devendra D. Pathak
Article
  • 1 Downloads

Abstract

A simple, one-pot, three-component, green synthesis of a wide range of propargylamines is reported by A3-coupling (aldehyde, alkyne and amine) via C–H activation of alkynes using [Zn(l-proline)2] as an efficient and reusable heterogeneous catalyst. High catalytic activity was achieved in comparatively low temperature under solvent-free conditions. All reactions were carried out in an open atmosphere without the use of any co-catalyst/additive.

Graphical Abstract

Keywords

C–C and C–N coupling reaction C–H activation Propargylamines [Zn(l-proline)2

Notes

Acknowledgements

We are thankful to the CRF IIT (ISM), Dhanbad and SAIF Panjab University, Chandigarh for providing help in the analysis of the samples. Samaresh Layek, Bhumika Agrahari and Anuradha acknowledges the receipt of IIT (ISM) fellowship. Shweta Kumari also acknowledges the receipt of Dr. D.S. Kothari Post-Doctoral Fellowship.

Supplementary material

10562_2018_2449_MOESM1_ESM.pdf (2.3 mb)
Supplementary material 1 (PDF 2338 KB)

References

  1. 1.
    Sheldon RA (2012) Chem Soc Rev 41:1437CrossRefGoogle Scholar
  2. 2.
    Domling A (2006) Chem Rev 106:17CrossRefGoogle Scholar
  3. 3.
    Peshkov VA, Pereshivko OP, Van der Eycken EV (2012) Chem Soc Rev 41:3790CrossRefGoogle Scholar
  4. 4.
    Saha TK, Das R (2018) Chem Select 3:12206Google Scholar
  5. 5.
    Li CJ (2010) Acc Chem Res 43:581CrossRefGoogle Scholar
  6. 6.
    Lauder K, Toscani A, Scalacci N, Castagnolo D (2017) Chem Rev 117:14091CrossRefGoogle Scholar
  7. 7.
    Corbett JW, Ko AS, Rodgers JD, Cearhart LA, Magnus NA, Bacheler LT, Diamond S, Jeffrey S, Klabe RM, Cordova BC, Garber S, Logue K, Trainor GL, Anderson PS, Erickson-Viitanen SK (2000) J Med Chem 43:2019CrossRefGoogle Scholar
  8. 8.
    Swithenbank C, McNulty PJ, Viste KL (1971) J Agric Food Chem 19:417CrossRefGoogle Scholar
  9. 9.
    Boulton AA, Davis BA, Durden DA, Dyck LE, Juorio AV, Li XM, Paterson IA, Yu PH (1997) Drug Dev Res 42:15156CrossRefGoogle Scholar
  10. 10.
    Koniashi M, Ohkuma H, Tsuno T, Oki T, VanDuyne GD, Clardy J (1990) J Am Chem Soc 112:3715CrossRefGoogle Scholar
  11. 11.
    Wright JL, Gregory TF, Kesten SR, Boxer PA, Serpa KA, Meltzer LT, Wise LD (2000) J Med Chem 43:3408CrossRefGoogle Scholar
  12. 12.
    Samai S, Nandi GC, Singh MS (2010) Tetrahedron Lett 51:5555CrossRefGoogle Scholar
  13. 13.
    Murai M, Mutoh Y, Ohta Y, Murakami M (2004) J Am Chem Soc 126:5968CrossRefGoogle Scholar
  14. 14.
    Bloch R (1998) Chem Rev 98:1407CrossRefGoogle Scholar
  15. 15.
    Murai T, Mutoh Y, Ohta Y, Murakami M (2004) J Am Chem Soc 126:5968CrossRefGoogle Scholar
  16. 16.
    Teimouri A, Chermahini AN, Narimani M (2012) Bull Korean Chem Soc 33:1556CrossRefGoogle Scholar
  17. 17.
    Xiong X, Chen H, Zhu R (2014) Chin J Catal 35:2006CrossRefGoogle Scholar
  18. 18.
    Wei C, Li CJ (2002) Green Chem 4:39CrossRefGoogle Scholar
  19. 19.
    Ramu E, Varala R, Sreelatha N, Adapa SR (2007) Tetrahedron Lett 48:7184CrossRefGoogle Scholar
  20. 20.
    Wei C, Li Z, Li C (2003) J Org Lett 5:4473CrossRefGoogle Scholar
  21. 21.
    Wei C, Li CJ (2003) J Am Chem Soc 125:9584CrossRefGoogle Scholar
  22. 22.
    Chen WW, Nguyen RV, Li CJ (2009) Tetrahedron Lett 50:2895CrossRefGoogle Scholar
  23. 23.
    Raghuvanshi DS, Singh KN (2011) Syn Lett 3:373Google Scholar
  24. 24.
    Zhang Y, Li P, Wang M, Wang L (2009) J Org Chem 74:4364CrossRefGoogle Scholar
  25. 25.
    Yadav JS, Reddy BVS, Gopal AVH, Patil KS (2009) Tetrahedron Lett 50:3493CrossRefGoogle Scholar
  26. 26.
    Hua LP, Lei W (2005) Chin J Chem 23:1076CrossRefGoogle Scholar
  27. 27.
    Zhang Q, Chen JX, Gao WX, Ding JC, Wu HY (2010) Appl Organometal Chem 24:809CrossRefGoogle Scholar
  28. 28.
    Kumari S, Shekhar A, Pathak DD (2016) RSC Adv 6:15340CrossRefGoogle Scholar
  29. 29.
    Li P, Wang L, Zhang Y, Wang M (2008) Tetrahedron Lett 49:6650CrossRefGoogle Scholar
  30. 30.
    Mallampati R, Valiyaveettil S (2014) ACS Sustain Chem Eng 2:855CrossRefGoogle Scholar
  31. 31.
    Zhang X, Corma A (2008) Angew Chem Int Ed 47:4358CrossRefGoogle Scholar
  32. 32.
    Borah BJ, Borah SJ, Saikia K, Dutta DK (2014) Catal Sci Technol 4:4001CrossRefGoogle Scholar
  33. 33.
    Layek K, Chakravarti R, Kantam ML, Maheswarana H, Vinu A (2011) Green Chem 13:2878CrossRefGoogle Scholar
  34. 34.
    Bosica G, Abdilla R (2017) J Mol Catal A 426:542CrossRefGoogle Scholar
  35. 35.
    Silva TLD, Rambo RS, Rampon DS, Radatz CS, Benvenutti EV, Russowsky D, Schneider PH (2015) J Mol Catal A 399:71CrossRefGoogle Scholar
  36. 36.
    Kidwai M, Bansal V, Mishra NK, Kumar A, Mozumda S (2007) Synlett 10:1581CrossRefGoogle Scholar
  37. 37.
    Kantam ML, Laha S, Yadav J, Bhargava S (2008) Tetrahedron Lett 49:3083CrossRefGoogle Scholar
  38. 38.
    Albaladejo MJ, Alonso F, Moglie Y, Yus M (2012) Eur J Org Chem 2012:3031CrossRefGoogle Scholar
  39. 39.
    Afraj SN, Chen C, Lee GH (2014) RSC Adv 4:26301CrossRefGoogle Scholar
  40. 40.
    Kidwai M, Jain A, Poddar R (2011) J Organomet Chem 696:1939CrossRefGoogle Scholar
  41. 41.
    Rocha MPD, Oliveira AR, Albuquerque TB, da Silva CDG, Domingues KNLC (2016) RSC Adv 6:4979CrossRefGoogle Scholar
  42. 42.
    Darbre T, Machuquerio M (2003) Chem Commun 1090Google Scholar
  43. 43.
    Sivamurugan V, Deepa K, Palanichamy M, Murugesan V (2004) Synth Commun 34:3833CrossRefGoogle Scholar
  44. 44.
    Poddar R, Jain A, Kidwai M (2007) J Adv Res 8:245CrossRefGoogle Scholar
  45. 45.
    Kantam ML, Balasubrahmanyam V, Shiva KKB, Venkanna GT (2007) Tetrahedron Lett 48:7332CrossRefGoogle Scholar
  46. 46.
    Satyanarayana KVV, Ramaiah PA, Murty YLN, Chandra MR, Pammi SVN (2012) Catal Commun 25:50CrossRefGoogle Scholar
  47. 47.
    Movahedi F, Masrouri H, Kassaee MZ (2014) J Mol Catal A 395:52CrossRefGoogle Scholar
  48. 48.
    Layek S, Kumari S, Anuradha, Agrahari B, Ganguly R, Pathak DD (2016) Inorg Chim Acta 453:735CrossRefGoogle Scholar
  49. 49.
    Layek S, Anuradha, Agrahari B, Pathak DD (2017) J Organomet Chem 846:105CrossRefGoogle Scholar
  50. 50.
    Agrahari B, Layek S, Anuradha, Ganguly R, Pathak DD (2018) Inorg Chim Acta 471:345CrossRefGoogle Scholar
  51. 51.
    Anuradha, Layek S, Agrahari B, Pathak DD (2017) Chem Select 2:6865Google Scholar
  52. 52.
    Li P, Regati S, Huang HC, Arman HD, Chen BL, Zhao JCG (2015) Chin Chem Lett 26:6CrossRefGoogle Scholar
  53. 53.
    Eagalapati NP, Rajack A, Murthy YLN (2014) J Mol Catal A 381:126CrossRefGoogle Scholar
  54. 54.
    Jeganathan M, Dhakshinamoorthy A, Pitchuman K (2014) ACS Sustain Chem Eng 2:781CrossRefGoogle Scholar
  55. 55.
    Kofoed J, Darbre T, Reymond JL (2006) Chem Commun 1482Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Samaresh Layek
    • 1
  • Bhumika Agrahari
    • 1
  • Shweta Kumari
    • 1
  • Anuradha
    • 1
  • Devendra D. Pathak
    • 1
  1. 1.Department of Applied ChemistryIndian Institute of Technology (ISM)DhanbadIndia

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