Skip to main content
SpringerLink
Log in

Three-Component Coupling of Aldehyde, Alkyne, and Amine via C–H Bond Activation Using Indium-Based Metal–Organic Framework Mil-68(In) as a Recyclable Heterogeneous Catalyst

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A porous indium-based metal–organic framework MIL-68(In) was prepared, and used as a recyclable catalyst for the one-pot three-component coupling of aldehydes, alkynes, and amines to form propargylamines via C–H bond activation. The transformation could proceed readily to produce propargylamines in the presence of a catalytic amount of MIL-68(In). The solvent significantly afftected the reaction, and toluene was the solvent of choice for the coupling transformation using MIL-68(In) catalyst. The reaction could only occur to produce propargylamines in the presence of the solid In-MOF catalyst. The MIL-68(In) catalyst could be reused several times for the synthesis of propargylamines. To our best knowledge, In-MOFs were not previously employed as heterogeneous catalyst for the synthesis of propargylamines from the one-pot three-component coupling of aldehydes, alkynes, and amines via C–H bond activation.

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

Scheme 1
Fig. 1
Fig. 2
Scheme 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

References

  1. Samai S, Nandi GC, Singh MS (2010) Tetrahedron Lett 51:5555–5558

    Article  CAS  Google Scholar 

  2. Miura M, Enna M, Okuro K, Nomura M (1995) J Org Chem 60:4999–5004

    Article  CAS  Google Scholar 

  3. Konishi M, Ohkuma H, Tsuno T, Oki T, VanDuyne GD, Clardy J (1990) J Am Chem Soc 112:3715–3716

    Article  CAS  Google Scholar 

  4. Li P, Wang L (2007) Tetrahedron 63:5455–5459

    Article  CAS  Google Scholar 

  5. Jung ME, Huang A (2000) Org Lett 2:2659–2661

    Article  CAS  Google Scholar 

  6. Murai T, Mutoh Y, Ohta Y, Murakami M (2004) J Am Chem Soc 124:5968–5969

    Article  Google Scholar 

  7. Rosas N, Sharma P, Alvarez C, Gómez E, Gutiérrez Y, Méndez M, Toscano RA, Maldonado LA (2003) Tetrahedron Lett 44:8019–8022

    Article  CAS  Google Scholar 

  8. Wei C, Li Z, Li C-J (2003) Org Lett 5:4473–4475

    Article  CAS  Google Scholar 

  9. Wei C, Li C-J (2003) J Am Chem Soc 125:9584–9585

    Article  CAS  Google Scholar 

  10. Lo VK-Y, Liu Y, Wong M-K, Che C-M (2006) Org Lett 8:1529–1532

    Article  CAS  Google Scholar 

  11. Bisai A, Singh VK (2006) Org Lett 8:2405–2408

    Article  CAS  Google Scholar 

  12. Gommermann N, Koradin C, Polborn K, Knochel P (2003) Angew Chem Int Ed 42:5763–5766

    Article  CAS  Google Scholar 

  13. Wang M, Li P, Wang L (2008) Eur J Org Chem 2008(13):2255–2261

    Article  Google Scholar 

  14. Luz I, Xamena FXLi, Corma A (2012) J Catal 285:285–291

    Article  CAS  Google Scholar 

  15. Zhang Y, Li P, Wang M, Wang L (2009) J Org Chem 74:4364–4367

    Article  CAS  Google Scholar 

  16. R.F.d. Luis, J. Orive, E.S. Larrea, M.K. Urtiaga, M.I. Arriortua, CrystEngComm 16 (2014) 10332-10366

  17. Furukawa S, Reboul J, Diring S, Sumida K, Kitagawa S (2014) Chem Soc Rev 43:5700–5734

    Article  CAS  Google Scholar 

  18. Cabello CP, Arean CO, Parra JB, Ania CO, Rumori P, Palomino GT (2015) Dalton Trans 44:9955–9963

    Article  Google Scholar 

  19. McDonald TM, Bloch ED, Long JR (2015) Chem Commun 51:4985–4988

    Article  CAS  Google Scholar 

  20. Gu J-Z, Cui Y-H, Wu J, Kirillov AM (2015) RSC Adv 5:78889–78901

    Article  CAS  Google Scholar 

  21. Li C, Sun M, Xu L, Wang Y, Huang J (2016) Cryst Eng Comm 18:596–600

    Article  CAS  Google Scholar 

  22. Dang GH, Dang TT, Le DT, Truong T, Phan NTS (2014) J Catal 319:258–264

    Article  CAS  Google Scholar 

  23. Ding B, Guo C, Liu SX, Cheng Y, Wu XX, Su XM, Liu YY, Li Y (2016) RSC Adv 6:33888–33900

    Article  CAS  Google Scholar 

  24. Schneemann A, Bon V, Schwedler I, Senkovska I, Kaskel S, Fischer RA (2014) Chem Soc Rev 43:6062–6096

    Article  CAS  Google Scholar 

  25. Allendorf MD, Stavila V (2015) CrystEngComm 17:229–246

    Article  CAS  Google Scholar 

  26. Chowdhuri AR, Bhattacharya D, Sahu SK (2016) Dalton Trans 45:2963–2973

    Article  Google Scholar 

  27. Duan T-W, Yan B (2015) J Mater Chem C 3:2823–2830

    Article  CAS  Google Scholar 

  28. Yan X, Lu N, Fan B, Bao J, Pan D, Wang M, Li R (2015) Cryst Eng Comm 17:6426–6433

    Article  CAS  Google Scholar 

  29. Trivedi M, Bhaskaran, Kumar A, Singh G, Kumar A, Rath NP (2016) New J Chem 40:3109–3118

    Article  CAS  Google Scholar 

  30. Liu H, Wang Q, Zhang M, Jiang J (2015) Cryst Eng Comm 17:4793–4798

    Article  CAS  Google Scholar 

  31. García-García P, Müller M, Corma A (2014) Chem Sci 5:2979–3007

    Article  Google Scholar 

  32. Chughtai AH, Ahmad N, Younus HA, Laypkov A, Verpoort F (2015) Chem Soc Rev 44:6804–6849

    Article  CAS  Google Scholar 

  33. Sharma N, Ojha H, Bharadwaj A, Pathak DP, Sharma RK (2015) RSC Adv 5:53381–53403

    Article  CAS  Google Scholar 

  34. Liu J, Chen L, Cui H, Zhang J, Zhang L, Su C-Y (2014) Chem Soc Rev 43:6011–6061

    Article  CAS  Google Scholar 

  35. Santiago-Portillo A, Navalón S, Cirujano FG (2015) FXLi Xamena, M Alvaro, H Garcia. ACS Catal 5:3216–3224

    Article  CAS  Google Scholar 

  36. Ghasempour H, Tehrani AA, Morsali A, Wang J, Junk PC (2016) Cryst Eng Comm 18:2463–2468

    Article  CAS  Google Scholar 

  37. W Zhen, H Gao, B Tian, J Ma, G Lu (2016) ACS Appl Mater Interfaces In press. 10.1021/acsami.1025b12524

  38. Dau PV, Cohen SM (2015) Inorg Chem 54:3134–3138

    Article  CAS  Google Scholar 

  39. Mo K, Yang Y, Cui Y (2014) J Am Chem Soc 136:1746–1749

    Article  CAS  Google Scholar 

  40. Liu Y, Moon S-Y, Hupp JT, Farha OK (2015) ACS Nano 9:12358–12364

    Article  CAS  Google Scholar 

  41. Klet RC, Tussupbayev S, Borycz J, Gallagher JR, Stalzer MM, Miller JT, Gagliardi L, Hupp JT, Marks TJ, Cramer CJ, Delferro M, Farha OK (2015) J Am Chem Soc 137:15680–15683

    Article  CAS  Google Scholar 

  42. Han Q, Sun X, Li J, Ma P, Niu J (2014) Inorg Chem 53:6107–6112

    Article  CAS  Google Scholar 

  43. Li P-Z, Wang X-J, Liu J, Lim JS, Zou R, Zhao Y (2016) J Am Chem Soc 138:2142–2145

    Article  CAS  Google Scholar 

  44. Dang GH, Lam HQ, Nguyen AT, Le DT, Truong T, Phan NTS (2016) J Catal 337:167–176

    Article  CAS  Google Scholar 

  45. Truong T, Nguyen KD, Doan SH, Phan NTS (2016) Appl Catal A Gen 510:27–33

    Article  CAS  Google Scholar 

  46. Nguyen VT, Ngo HQ, Le DT, Truong T, Phan NTS (2016) Chem Eng J 284:778–785

    Article  CAS  Google Scholar 

  47. Wang X, Li Y (2016) J Mol Catal A 420:56–65

    Article  CAS  Google Scholar 

  48. Kim J, McNamara ND, Hicks JC (2016) Appl Catal A Gen 517:141–150

    Article  CAS  Google Scholar 

  49. Rafiee E, Nobakht N (2015) J Mol Catal A 398:17–25

    Article  CAS  Google Scholar 

  50. Hou J, Luan Y, Tang J, Wensley AM, Yang M, Lu Y (2015) J Mol Catal A 407:53–59

    Article  CAS  Google Scholar 

  51. Zhang F, Shi J, Jin Y, Fu Y, Zhong Y, Zhu W (2015) Chem Eng J 259:183–190

    Article  CAS  Google Scholar 

  52. Cui H, Wang Y, Wang Y, Fan Y-Z, Zhang L, Su C-Y (2016) Cryst Eng Comm 18:2203–2209

    Article  CAS  Google Scholar 

  53. Abednatanzi S, Abbasi A, Masteri-Farahani M (2015) New J Chem 39:5322–5328

    Article  CAS  Google Scholar 

  54. Ji W, Hu H, Zhang W, Huang H, He X, Han X, Zhao F, Liu Y, Kang Z (2013) Dalton Trans 42:10690–10693

    Article  CAS  Google Scholar 

  55. Volkringer C, Meddouri M, Loiseau T, Guillou N, Marrot J, Férey G, Haouas M, Taulelle F, Audebrand N, Latroche M (1901) Inorg Chem 47(2008):11892–11901

    Google Scholar 

  56. Ji W-J, Zhai Q-G, Li S-N, Jiang Y-C, Hu M-C (2012) Inorg Chem Commun 24:209–211

    Article  CAS  Google Scholar 

  57. Qian J, Jiang F, Yuan D, Li X, Zhang L, Su K, Hong M (2013) J Mater Chem A 1:9075–9082

    Article  CAS  Google Scholar 

  58. Aguirre-Díaz LM, Iglesias M, Snejko N, Gutiérrez-Puebla E, Monge MÁ (2013) Cryst Eng Comm 15:9562–9571

    Article  Google Scholar 

  59. Gomez-Lor B, Gutie´rrez-Puebla E, Iglesias M, Monge MA, Ruiz-Valero C, Snejko N (2012) Inorg Chem 41:2429–2432

    Article  Google Scholar 

  60. Xia J, Xu J, Fan Y, Song T, Wang L, Zheng J (2014) Inorg Chem 53:10024–10026

    Article  CAS  Google Scholar 

  61. Selvin R, Hsu H-L, Her T-M (2008) Catal Commun 10:169–172

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The Vietnam National University—Ho Chi Minh City (VNU-HCM) is acknowledged for financial support through Project No. B2015-20-03.

Author information

Authors and Affiliations

  1. Department of Chemical Engineering, HCMC University of Technology, VNU-HCM, 268 Ly Thuong Kiet, District 10, Ho Chi Minh City, Vietnam

    Hanh N. K. Lam, Nguyen B. Nguyen, Giao H. Dang, Thanh Truong & Nam T. S. Phan

Authors
  1. Hanh N. K. Lam
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nguyen B. Nguyen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Giao H. Dang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Thanh Truong
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Nam T. S. Phan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Thanh Truong or Nam T. S. Phan.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2503 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lam, H.N.K., Nguyen, N.B., Dang, G.H. et al. Three-Component Coupling of Aldehyde, Alkyne, and Amine via C–H Bond Activation Using Indium-Based Metal–Organic Framework Mil-68(In) as a Recyclable Heterogeneous Catalyst. Catal Lett 146, 2087–2097 (2016). https://doi.org/10.1007/s10562-016-1805-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-016-1805-7

Keywords

Search

Navigation