Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

TMEDA: Efficient and Mild Catalyst for the Acylation of Alcohols, Phenols and Thiols under Solvent-free Condition

  • Published : 2009.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

N,N,N′,N′-tetramethylethylenediamine (TMEDA) acts as a simple, mild and efficient catalyst for the acylation of alcohols, phenols and thiols at room temperature under solvent-free condition. Acylation reaction with acetic anhydride and benzoic anhydride proceeds with good to excellent yield in the presence of TMEDA as the catalyst.

Keywords

References

  1. Larock, R. C. Comprehensive Organic Transformation, 2nd ed.; Wiley-VCH: New York, 1996; 1999; p1955
  2. Comprehensive Organic Synthesis; Torst, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1992; Vol. 6
  3. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Syntheis, 2nd ed.; Wiely-VCH: New York, 1991; Chapter 7 and 3rd ed.; 1999; pp 150-160
  4. Hofle, G.; Steglich, W.; Vorbruggen, H. Angew. Chem. Int. Ed. Eng. 1978, 17, 569 https://doi.org/10.1002/anie.197805691
  5. Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115, 3358 https://doi.org/10.1021/ja00061a056
  6. Iqbal, J.; Srivastava, R. R. J. Org. Chem. 1992, 57, 2001 https://doi.org/10.1021/jo00033a020
  7. Dey, S. K. Tetrahedron Lett. 2003, 45, 2919
  8. Tale, R. H.; Adude, R. N. Tetrahedron Lett. 2006, 47, 7263 https://doi.org/10.1016/j.tetlet.2006.07.046
  9. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61, 4560 https://doi.org/10.1021/jo952237x
  10. Kamal, A.; Khan, M. A.; Reddy, S. Y.; Srikant, V. V.; Krishnaji, T. Tetrahedron Lett. 2007, 48, 3813 https://doi.org/10.1016/j.tetlet.2007.03.162
  11. Saravanan, P.; Singh, V. Tetrahedron Lett. 1999, 40, 2611 https://doi.org/10.1016/S0040-4039(99)00229-4
  12. Nakae, Y.; Kusaki, I.; Sato, T. Synlett 2001, 1584
  13. Kondasamy, J. K.; Chaand, D. K. J. Mol Catal. A: Chem. 2006, 255, 275 https://doi.org/10.1016/j.molcata.2006.04.026
  14. Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583 https://doi.org/10.1021/ol0264760
  15. Schumacher J. C. Perchlorates-Their Properties, Manufacture and use in ACS Monograph Searies; Reinhold: New York, 1996
  16. Costa, M.; Chiusoli, G. P.; Taffurelli, D.; Dalmonego, G. J. Chem. Soc. Perkin Trans 1, 1998, 1541
  17. Kovacevic, B.; Maksic, Z. B. Org. Lett. 2001, 3, 1523 https://doi.org/10.1021/ol0158415
  18. Yamamota, Y.; Kojima, S. In The Chemistry of Amidines and Imidates; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1991; Vol. 2, p 485
  19. Wei, T. B.; Lin, Q.; Zhang, Y. M.; Wang, H. Synth. Commun. 2004, 34, 2205 https://doi.org/10.1081/SCC-120038502
  20. Chauhan, M.; Boudjouk, P. Can. J. Chem. 2000, 78, 1396 https://doi.org/10.1139/cjc-78-11-1396
  21. Nishiyama, H.; Furuta, A. Chem. Commun. 2007, 760
  22. Minakata, S.; Okada, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2005, 7, 3509 https://doi.org/10.1021/ol051186f
  23. Sano, T.; Ohashi, K.; Oriyama, T. Synthesis 1999, 1141
  24. Kim, S. S.; Song, D. H. Eur. J. Org. Chem. 2005, 1777
  25. Kim, S. S.; Lee, S. H. Synth. Commun. 2005, 35, 751 https://doi.org/10.1081/SCC-200050390
  26. Kim, S. S.; Lee, S. H. Kwak, J. M. Tetrahedron Asymmetry 2006, 17, 1165 https://doi.org/10.1016/j.tetasy.2006.04.011
  27. Kim, S. S.; Kwak, J. M. Tetrahedron 2006, 62, 49 https://doi.org/10.1016/j.tet.2005.09.131
  28. Kim, S. S.; Rajagopal, G.; Song, D. H. J. Organomet. Chem. 2004, 689, 1734 https://doi.org/10.1016/j.jorganchem.2004.01.025
  29. Kim. S. S.; Kim, D. W.; Rajagopal, G. Synthesis 2004, 213
  30. Kim, S. S.; Rajagopal, G.; Kim, D. W.; Song, D. H. Synth. Commun. 2004, 34, 2973 https://doi.org/10.1081/SCC-200026652
  31. Kim, S. S.; Rajagopal, G. Synthesis 2007, 215
  32. Kim, S. S.; Kadam, S. T. Bull. Korean Chem. Soc. 2008, 29, 1320 https://doi.org/10.5012/bkcs.2008.29.7.1320
  33. Kim, S. S.; Kadam, S. T. Catal. Commun. 2008, 9, 1342 https://doi.org/10.1016/j.catcom.2007.11.030
  34. Kadam, S. T.; Kim, S. S. Synthesis 2008, 267
  35. Kadam, S. T.; Kim, S. S. Synthesis 2008, 20, 3307
  36. Khazaei, A.; Rostami, A.; Tanbakouchian, Z.; Zinati, Z. Catal. Commun. 2006, 7, 214 https://doi.org/10.1016/j.catcom.2005.11.010
  37. Zolfigol, M. A.; Khazaei, A.; Cjoghamarani, A. G.; Rostami, A.; Hajjami, M. Catal. Commun. 2006, 7, 399 https://doi.org/10.1016/j.catcom.2005.12.004
  38. Dalpozzo, R.; Nino, A. D.; Maiulo, L.; Oliverio, M.; Procopio, A.; Russo, B.; Tocci, A. Aus. J. Chem. 2007, 60, 75 https://doi.org/10.1071/CH06346
  39. Zhag, L.; Luo, Y.; Fan, Renhua, F.; Wu, J. Green Chem. 2007, 9, 1022 https://doi.org/10.1039/b702646c
  40. Chakraborti, A. K.; Sharma, L.; Gilhane, R.; Shivani. Tetrahedron 2003, 59, 7661 https://doi.org/10.1016/j.tet.2003.08.007
  41. Shangjie, Xu.; Ingmar, H.; Bernhard, K.; Herbert, M.; Wolfgang, S.; Hendrik, Z. Chem. Eur. J. 2005, 11, 4751 https://doi.org/10.1002/chem.200500398

Cited by

  1. Efficient Routes to Racemic and Enantiomerically Pure (S)-BINOL Diesters vol.43, pp.23, 2013, https://doi.org/10.1080/00397911.2013.774017
  2. Acetylation of alcohols with acetic anhydride promoted by N,N,N-trimethylanilinium tribromide vol.49, pp.12, 2013, https://doi.org/10.1134/S1070428013120026
  3. Rice Husk Ash: A New, Cheap, Efficient, and Reusable Reagent for the Protection of Alcohols, Phenols, Amines, and Thiols vol.189, pp.5, 2014, https://doi.org/10.1080/10426507.2013.844142
  4. Direct coupling reaction between alcohols and allyltrimethylsilane catalyzed by phosphomolybdic acid pp.10990739, 2010, https://doi.org/10.1002/aoc.1527
  5. ChemInform Abstract: TMEDA: Efficient and Mild Catalyst for the Acylation of Alcohols, Phenols and Thiols under Solvent-Free Condition. vol.40, pp.39, 2009, https://doi.org/10.1002/chin.200939042
  6. Green and Efficient Method for the Acylation of Amines and Phenols in the Presence of Hydrotalcite in Water vol.36, pp.10, 2012, https://doi.org/10.3184/174751912x13460810792101