DOI QR코드

DOI QR Code

Use of an Ionic Liquid as a Co-solvent for Recyclable Pd/C-mediated N-Debenzylation

  • Choi, Jin-Kyu (Department of Chemistry, College of Natural Sciences, Seoul National University) ;
  • Jeon, Byung-Sun (Department of Chemistry, College of Natural Sciences, Seoul National University) ;
  • Cho, Jong-Hyun (Department of Chemistry, College of Natural Sciences, Seoul National University) ;
  • Kim, B.-Moon (Department of Chemistry, College of Natural Sciences, Seoul National University)
  • Published : 2010.03.20

Abstract

Keywords

References

  1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991.
  2. Kocienski, P. J. Protecting Groups; Georg Thieme Stuttgart: New York, 1994.
  3. Bernotas, R. C.; Cube, R. V. Synth. Commun. 1990, 20, 1209-1212. https://doi.org/10.1080/00397919008052829
  4. Cheng, C.; Sun, J.; Xing, L.;Xu, J.; Wang, X.; Hu, Y. J. Org. Chem. 2009, 74, 5671-5674. https://doi.org/10.1021/jo9007282
  5. David, A.; Vannice, M. A. J. Catal. 2006, 237, 349-358. https://doi.org/10.1016/j.jcat.2005.11.017
  6. Gonzlez-Sabn, J.; Gotor, V.; Rebolledo, F. J. Org. Chem. 2007, 72,1309-1314. https://doi.org/10.1021/jo062205h
  7. Kuehne, M. E.; Cowen, S. D.; Xu, F.; Borman, L.J. Org. Chem. 2001, 66, 5303-5316. https://doi.org/10.1021/jo000249z
  8. Asahina, Y.; Takei, M.;Kimura, T.; Fukuda, Y. J. Med. Chem. 2008, 51, 3238-3249. https://doi.org/10.1021/jm701428b
  9. Means, G. E.; ElAmin, B.; Anantharamaiah,G. M.; Royer, G. P. J. Org. Chem. 1979, 44, 3442-3444. https://doi.org/10.1021/jo01333a048
  10. Periasamy, M.; Kanth, J. V. B.; Reddy, C. K. Synth. Commun.1994, 94, 313-319.
  11. Ram, S.; Spicer, L. D. Tetrahedron Lett. 1987, 28, 515-516. https://doi.org/10.1016/S0040-4039(00)95769-1
  12. Arefalk, A.; Larhed, M.; Hallberg, A. J. Org. Chem. 2005, 70,938-942. https://doi.org/10.1021/jo048187q
  13. Deaton-Rewolinski, M. V.; Kelleman, A.; Haddach, A. A. Tetrahedron Lett. 2002, 43, 399-402. https://doi.org/10.1016/S0040-4039(01)02192-X
  14. Banerji, A.; Talukdar, S.; Nayak, S. K. J. Org. Chem. 1998, 63,4925-4929. https://doi.org/10.1021/jo971751v
  15. Pandey, G.; Rani, K. S. Tetrahedron Lett. 1988,29, 4157-4158. https://doi.org/10.1016/S0040-4039(00)80443-8
  16. Grayson, E. J.; Davis, B. G. Org. Lett. 2005, 7, 2361-2364. https://doi.org/10.1021/ol050624f
  17. Chern, C.-Y.; Huang, Y.-P.; Kan, W. M. Tetrahedron Lett.2003, 44, 1039-1041. https://doi.org/10.1016/S0040-4039(02)02738-7
  18. Jansson, A. M.; Grotli, M.; Halkes, K. M.; Meldal, M. Org. Lett. 2002, 4, 27-30. https://doi.org/10.1021/ol016812x
  19. Mukhopadhyay, S.; Ratner, S.; Spernat,A.; Qafisheh, N.; Sasson, Y. Org. Process Res. Dev. 2002, 6, 297-300. https://doi.org/10.1021/op010047k
  20. Yu, J. Q.; Wu, H. C.; Ramarao, C.; Spencer, J. B.; Ley, S.V. Chem Commun. 2003, 678-679.
  21. Welton, T. Chem. Rev. 1999, 99, 2071-2083. https://doi.org/10.1021/cr980032t
  22. Wasserscheid, P.; Keim, W. Angew. Chem. Int. Ed. 2000, 39,3772-3789. https://doi.org/10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
  23. Tzschucke, C. C.; Markert, C.; Bannwarth, W.;Roller, S.; Hebel, A.; Hagg, R. Angew. Chem. Int. Ed. 2002, 41,3964-3940. https://doi.org/10.1002/1521-3773(20021104)41:21<3964::AID-ANIE3964>3.0.CO;2-3
  24. Dyson, P. J. Appl. Organometal. Chem. 2002, 16,495-500. https://doi.org/10.1002/aoc.337
  25. Dupont, J.; Souza, R. F.; Suarez, A. Z. Chem. Rev.2002, 102, 3367-3692.
  26. Oliver-Bourbigou, H.; Magna, L. J.Molecular Catalysis A: Chemical 2002, 182-183, 419-437. https://doi.org/10.1016/S1381-1169(01)00465-4
  27. Kou, Y.; Zhao, D.; Wu, M.; Min, E. Catalysis Today 2002, 74,157-189. https://doi.org/10.1016/S0920-5861(01)00541-7
  28. Welton, T. Coord. Chem. Rev. 2004, 248, 2459-2477. https://doi.org/10.1016/j.ccr.2004.04.015
  29. Parvulescu, V. I.; Hardacre, C. Chem. Rev. 2007, 107, 2615-2665. https://doi.org/10.1021/cr050948h
  30. Plechkova, N. V.; Seddon, K. R. Chem. Soc. Rev. 2008,37, 123-150. https://doi.org/10.1039/b006677j
  31. Weingartner, H. Angew. Chem. Int. Ed. 2008,47, 654-670. https://doi.org/10.1002/anie.200604951
  32. Gu, Y.; Li, G. Adv. Synth. Catal. 2009, 351,817-847. https://doi.org/10.1002/adsc.200900043
  33. Durand, J.; Teuma, E.; Gomez, M. Eur. J. Inorg. Chem. 2008, 3577-3586.
  34. Calo, V.; Nacci, A.; Monopoli, A. Eur. J. Org. Chem. 2006,3791-3802.
  35. Polshettiwar, V. Res. J. Chem. Environ. 2006, 10,91-92.
  36. Biffs, A.; Zecca, M.; Basato, M. J. Mol. Catal. A 2001, 173, 249. https://doi.org/10.1016/S1381-1169(01)00153-4
  37. Roland, G.; Heidenreich, R. G.; Krauter, J.G. E.; Pietsch, J.; Kohler, K. J. Mol. Catal. A 2002, 182-183,499-509. https://doi.org/10.1016/S1381-1169(01)00499-X
  38. Phan, N. T. S.; van der Sluys, M.; Jones, Ch. W. Adv. Synth. Catal. 2006, 348, 609. https://doi.org/10.1002/adsc.200505473
  39. Polshettiwar, V.; Molnar, A. Tetrahedron2007, 63, 6949. https://doi.org/10.1016/j.tet.2007.04.023
  40. Zhao, F.; Bhanage, B. M.; Shirai, M.;Arai, M. Chem. Eur. J. 2000, 6, 843-848. https://doi.org/10.1002/(SICI)1521-3765(20000303)6:5<843::AID-CHEM843>3.0.CO;2-G

Cited by

  1. ChemInform Abstract: Use of an Ionic Liquid as a Co-solvent for Recyclable Pd/C-Mediated N-Debenzylation. vol.41, pp.32, 2010, https://doi.org/10.1002/chin.201032063