Catalysis Letters

, Volume 144, Issue 11, pp 1803–1809 | Cite as

Chemoselective Transfer Hydrogenation of α,β-Unsaturated Carbonyls Using Palladium Immobilized Ionic Liquid Catalyst

  • Nilesh M. Patil
  • Takehiko Sasaki
  • Bhalchandra M. Bhanage


This work reports a simple and highly efficient protocol for chemoselective transfer hydrogenation of α,β-unsaturated carbonyls using immobilized palladium metal-containing ionic liquid as a versatile heterogeneous catalyst with an excellent conversion and chemoselectivity (up to 100 %). The influence of various reaction parameters such as the effect of hydrogen donor, solvent, temperature, and time were studied. The catalyst was recycled for four consecutive cycles without significant loss in the catalytic activity. The developed protocol is more advantageous due to the use of HCOONH4 as a hydrogen source, mild reaction conditions, and simple workup procedure and applicable for a wide range of substrates.

Graphical Abstract


Transfer hydrogenation Chemoselective Immobilization Palladium Heterogeneous catalyst 



The author (N. M. Patil) is greatly thankful to the UGC-SAP (University Grant Commission, India) for providing the Senior Research Fellowship. XPS measurements were conducted at the Research Hub for Advanced Nano Characterization, the University of Tokyo, supported by the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan. This work is supported by JSPS and DST under the Japan-India Science Cooperative Program.

Supplementary material

10562_2014_1362_MOESM1_ESM.docx (120 kb)
Supplementary material 1 (DOCX 119 kb)
10562_2014_1362_MOESM2_ESM.docx (2.3 mb)
Supplementary material 2 (DOCX 2338 kb)


  1. 1.
    Ehud K, Noam G (1986) J Am Chem Soc 108:7314–7325CrossRefGoogle Scholar
  2. 2.
    Huai GC, James MT, Wuts PGM, Tomi KS, Clark W Sm (1995) Int J Pept Protein Res 45: 1–10Google Scholar
  3. 3.
    Masuko K, Hiroshi S, Tojiro T, Kazuki S (1997) Cancer Lett 119:207–212CrossRefGoogle Scholar
  4. 4.
    Gallezot P, Richard D (1998) Catal Rev Sci Eng 40:81–126CrossRefGoogle Scholar
  5. 5.
    Saidulu G, Suresh M, Chinna KPN, Kamaraju SRR, David RB (2013) RSC Adv 3:11533–11538CrossRefGoogle Scholar
  6. 6.
    Sanjit KM, Rafique UI, Chiranjit A, Michael JW, Kaushik M (2014) ChemCatChem 6:1419–1426Google Scholar
  7. 7.
    Fang ZS, Lin H, Ji N, Yong C, He YH, Kang NF (2008) Chem Commun 30:3531–3533Google Scholar
  8. 8.
    Hidehito O, Eiji S, Tamio H (2007) Chem Commun 18:1819–1821Google Scholar
  9. 9.
    Anuj S, Vinod K, Arun KS (2006) Adv Synth Catal 348:354–360CrossRefGoogle Scholar
  10. 10.
    Xuefeng L, Liangchun L, Yuanfu T, Ling Z, Linfeng C, Jin Z, Jian L, Jingen D (2010) J Org Chem 75:2981–2988CrossRefGoogle Scholar
  11. 11.
    Wei-Jing L, Yun-Wei C, Xue-Long H (2008) Angew Chem Int Ed 47:10133–10136CrossRefGoogle Scholar
  12. 12.
    Yoel S, Jochanan B (1975) J Org Chem 40:1887–1896CrossRefGoogle Scholar
  13. 13.
    David SH, Matthias S, Gregory CF (1996) Org Chem 61:6751–6752CrossRefGoogle Scholar
  14. 14.
    Boqiang D, Zhenfeng Z, Yangang L, Masashi S, Tsuneo I, Wanbin Z (2013) Org Lett 15:3690–3693CrossRefGoogle Scholar
  15. 15.
    Mannepalli LK, Ramineni K, Jagjit Y, Medak S, Akula V (2012) Adv Synth Catal 354:663–669CrossRefGoogle Scholar
  16. 16.
    Lunxiang Y, Jurgen L (2007) Chem Rev 107:133–173CrossRefGoogle Scholar
  17. 17.
    Andrea S, Mark M, Mihaly O, Gabor D, Frank UR, Laszlo TM (2013) Green Chem 15:1857–1862CrossRefGoogle Scholar
  18. 18.
    Zoltan B, Zoltan F, Gyorgy K, Istvan H (2009) Green Chem 11:1937–1940CrossRefGoogle Scholar
  19. 19.
    Takehiko S, Chongmin Z, Mizuki T, Yasuhiro I (2005) Chem Commun 19:2506–2508Google Scholar
  20. 20.
    Takehiko S, Mizuki T, Chongmin Z, Takao K, Yasuhiro I (2008) J Mol Catal A: Chem 279:200–209CrossRefGoogle Scholar
  21. 21.
    Mayur VK (2013) Takehiko S, Bhalachandra M B. ACS Catal 3:287–293CrossRefGoogle Scholar
  22. 22.
    Mayur VK, Ajinkya RS, Takehiko S, Bhalachandra MB (2014) J Mol Catal A: Chem 385:91–97CrossRefGoogle Scholar
  23. 23.
    Dattatraya BB, Ziyauddin SQ, Kishor PD, Shoeb RK, Bhalchandra MB (2011) Green Chem 13:1490–1494CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Nilesh M. Patil
    • 1
  • Takehiko Sasaki
    • 2
  • Bhalchandra M. Bhanage
    • 1
  1. 1.Department of ChemistryInstitute of Chemical TechnologyMumbaiIndia
  2. 2.Department of Complexity Science and Engineering, Graduate School of Frontier SciencesThe University of TokyoKashiwaJapan

Personalised recommendations