Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

An Efficient Method for N-Formylation of Amines Using Natural HEU Zeolite at Room Temperature Under Solvent-Free Conditions

  • Bahari, Siavash (Department of Chemistry, Ahar Branch, Islamic Azad University) ;
  • Mohammadi-Aghdam, Babak (Department of Chemistry, Ahar Branch, Islamic Azad University) ;
  • Mohammad Sajadi, S. (Department of Petrolium Geoscience, Faculty of Sciences, University of Soran) ;
  • Zeidali, Fereshteh (Ilam petrochemical Complex)
  • 투고 : 2012.03.03
  • 심사 : 2012.04.02
  • 발행 : 2012.07.20
Download PDF
⟨ Previous Next ⟩

초록

A rapid and practical green route for N-formylation of primary and secondary amines with formic acid at room temperature under the solvent-free conditions using HEU zeolite as a heterogeneous, reusable and highly efficient catalyst is described. The process is remarkably simple and environmentally benign. Excellent chemoselectivity was observed for the conversion of primary amines in the presence of secondary amines.

키워드

참고문헌

  1. Kobayashi, K.; Nagato, S.; Kawakita, M.; Morikawa, O.; Konishi, H. Chem. Lett. 1995, 575.
  2. Chen, B. C.; Bednarz, M. S.; Zhao, R.; Sundeen, J. E.; Chen, P.; Shen, Z.; Skoumbourdis, A. P.; Barrish, J. C. Tetrahedron Lett. 2000, 41, 5453. https://doi.org/10.1016/S0040-4039(00)00910-2
  3. Downie, I. M.; Earle, M. J.; Heaney, H.; Shuhaibar, K. F. Tetrahedron 1993, 49, 4015. https://doi.org/10.1016/S0040-4020(01)89915-4
  4. Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 56, 6620.
  5. Kobayashi, S.; Yasuda, M.; Hachiya, I. Chem. Lett. 1996, 407.
  6. Martrniez, J.; Laur, J. Synthesis 1982, 979.
  7. Strazzolini, P.; Giumanini, A. G.; Cauci, S. Tetrahedron 1990, 46, 1081. https://doi.org/10.1016/S0040-4020(01)86676-X
  8. Blicke, F. F.; Lu, C. J. J. Am. Chem. Soc. 1952, 74, 3933. https://doi.org/10.1021/ja01135a503
  9. Waki, J.; Meienhofer, J. J. Org. Chem. 1977, 42, 2019. https://doi.org/10.1021/jo00431a046
  10. Chen, F. M. F.; Benoiton, N. L. Synthesis 1979, 709.
  11. Yale, H. L. J. Org. Chem. 1971, 36, 3238. https://doi.org/10.1021/jo00820a603
  12. Kisfaludy, L.; Laszlo, O. Synthesis 1987, 510.
  13. Neveux, M.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Perkin Trans. I 1991, 1197.
  14. Duczek, W.; Deutsch, J.; Vieth, S.; Niclas, H.-J. Synthesis 1996, 37.
  15. Reddy, P. G.; Kumar, G. D. K.; Baskaran, S. Tetrahedron Lett. 2000, 41, 9149. https://doi.org/10.1016/S0040-4039(00)01636-1
  16. Hill, D. R.; Hasiao, C.-N.; Kurukulasuriya, R.; Wittenberger, S. J. Org. Lett. 2002, 4, 111. https://doi.org/10.1021/ol016976d
  17. Hosseni-Sarvari, M.; Sharghi, H. J. Org. Chem. 2006, 71, 6652. https://doi.org/10.1021/jo060847z
  18. Biswanath, D.; Meddeboina, K.; Balasubramanayam. P.; Boyapati, V. D.; Nandan, K. D. Tetrahedron Lett. 2008, 49, 2225. https://doi.org/10.1016/j.tetlet.2008.02.050
  19. Chandra Shekhar, A.; Ravi Kumar, A.; Sathaiah, G.; Luke Paul, V.; Sridhar, M.; Rao, S. Tetrahedron Lett. 2009, 50, 7099. https://doi.org/10.1016/j.tetlet.2009.10.006
  20. Jung, S. H.; Ahn, J. H.; Park, S. K.; Choi, J.-K. Bull. Korean Chem. Soc. 2002, 23, 149. https://doi.org/10.5012/bkcs.2002.23.1.149
  21. Mamani, L.; Sheykhan, M.; Heydari, A.; Faraji, M.; Yamini, Y. Appl. Catal. A 2010, 377, 64. https://doi.org/10.1016/j.apcata.2010.01.020
  22. Mohammadi, B.; Hosseini Jamkarani, S. M.; Kamali, T. A.; Nasrollahzadeh, M.; Mohajeri, A. Turk. J. Chem. 2010, 34, 613.
  23. Nasrollahzadeh, M.; Bayat, Y.; Habibi, D.; Moshaee, S. Tetrahedron Lett. 2009, 50, 4435.
  24. Habibi, D.; Nasrollahzadeh, M. Synth. Commun. 2010, 40, 3159. https://doi.org/10.1080/00397910903370683
  25. Modarresi-Alam, A. R.; Nasrollahzadeh, M.; Khamooshi, F. Arkivoc 2007, xvi, 234.
  26. Modarresi-Alam, A. R.; Khamooshi, F.; Nasrollahzadeh, M.; Amirazizi, H. A. Tetrahedron 2007, 63, 8723. https://doi.org/10.1016/j.tet.2007.06.048
  27. Modarresi- Alam, A. R.; Nasrollahzadeh, M.; Khamooshi, F. Scientia Iranica 2008, 15, 452.
  28. Habibi, D.; Nasrollahzadeh, M. Monatsh fur Chem. 2011, DOI 10.1007/s00706-011-0670-8.
  29. Habibi, D.; Nasrollahzadeh, M.; Bayat, Y. Synth. Commun. 2011, 41, 2135. https://doi.org/10.1080/00397911.2010.497728
  30. Breck, D. W. Zeolite Molecular Sieves; Wiley: New York, 1974.
  31. Dyer, A. An Introduction to Zeolite Molecular Sieves; Chichester, 1988.
  32. Nasrollahzadeh, M.; Habibi, D.; Shahkarami, Z.; Bayat, Y. Tetrahedron 2009, 66, 3866.
  33. Tajbakhsh, M.; Mohajerani, B.; Heravi, M. M.; Ahmadi, A. N. J. Mol. Catal. A: Chem. 2005, 236, 216. https://doi.org/10.1016/j.molcata.2005.04.033
  34. Habibi, D.; Nasrollahzadeh, M.; Kamali, T. A. Green Chem. 2011, 13, 3499. https://doi.org/10.1039/c1gc15245a
  35. Das, B.; Krishnaiah, M.; Balasubramanayam, P.; Veeranjaneyulu, B.; Kumar, D. N. Tetrahedron Lett. 2008, 49, 2225. https://doi.org/10.1016/j.tetlet.2008.02.050
  36. Brahmachari, G.; Laskar, S. Tetrahedron Lett. 2010, 51, 2319. https://doi.org/10.1016/j.tetlet.2010.02.119
  37. Deutsch, J.; Eckelt, R.; Kockritz, A.; Martin, A. Tetrahedron 2009, 65, 10365. https://doi.org/10.1016/j.tet.2009.10.047
  38. Tumma, H.; Nagaraju, N.; Reddy, K. V. J. Mol. Catal. A: Chem. 2009, 310, 121. https://doi.org/10.1016/j.molcata.2009.06.007
  39. Muthukur Bhojegowd, M. R.; Nizam, A.; Pasha, M. A. Chin. J. Catal. 2010, 31, 518. https://doi.org/10.1016/S1872-2067(09)60064-4
  40. Kaboudin, B.; Khodamorady, M. Synlett 2010, 2905.
  41. Rahman, M.; Kundu, D.; Hajra, A.; Majee, A. Tetrahedron Lett. 2010, 51, 2896. https://doi.org/10.1016/j.tetlet.2010.03.097

피인용 문헌

  1. Catalytic amide formation from non-activated carboxylic acids and amines vol.43, pp.8, 2014, https://doi.org/10.1039/C3CS60345H
  2. Plant-mediated green synthesis of ZnO nanoparticles using Garcinia gummi-gutta seed extract: Photoluminescence, screening of their catalytic activity in antioxidant, formylation and biodiesel production vol.132, pp.8, 2017, https://doi.org/10.1140/epjp/i2017-11627-1
  3. Sulfated polyborate-catalyzed N-formylation of amines: a rapid, green and efficient protocol vol.14, pp.12, 2017, https://doi.org/10.1007/s13738-017-1186-x
  4. H) as a heterogeneous and recyclable nanocatalyst for the formylation of alcohols and amines under solvent-free conditions vol.41, pp.12, 2017, https://doi.org/10.1039/C7NJ00417F
  5. -formylating agents vol.47, pp.2, 2017, https://doi.org/10.1080/00397911.2016.1255334
  6. Biosynthesised ZnO : Dy3+ nanoparticles: Biodiesel properties and reusable catalyst for N-formylation of aromatic amines with formic acid vol.133, pp.4, 2018, https://doi.org/10.1140/epjp/i2018-11963-6
  7. K4[Fe(CN)6] as Non-Toxic Source of Cyanide for the Cyanation of Aryl Halides using Pd-Beta Zeolite as a Heterogeneous Catalyst vol.37, pp.10, 2012, https://doi.org/10.3184/174751913x13787959859425
  8. Nano Cerium Oxide as a Recyclable Catalyst for the Synthesis of N-Monosubstituted Ureas with the Aid of Acetaldoxime as an effective Water Surrogate vol.37, pp.10, 2013, https://doi.org/10.3184/174751913x13787959859461
  9. CoFe2O4 Nanoparticles as a Magnetically Recoverable and Reusable Catalyst for the Synthesis of Arylaminotetrazoles and 5-aryloxytetrazoles vol.38, pp.2, 2014, https://doi.org/10.3184/174751914x13871210981307
  10. Preparation, characterization and application of nanosized CuO/HZSM-5 as an efficient and heterogeneous catalyst for the N-formylation of amines at room temperature vol.471, pp.None, 2012, https://doi.org/10.1016/j.jcis.2016.02.062
  11. Recent advances in N-formylation of amines and nitroarenes using efficient (nano)catalysts in eco-friendly media vol.21, pp.19, 2019, https://doi.org/10.1039/c9gc01822k
  12. Critical Role of CUS in the Au/MOF-808(Zr) Catalyst for Reaction of CO2 with Amine/H2 via N-Methylation and N-Formylation vol.59, pp.14, 2012, https://doi.org/10.1021/acs.iecr.0c00242
  13. Sulfated TiO2/SnO2 nanocomposite as a green heterogeneous catalyst for direct amide formation reaction vol.3, pp.None, 2012, https://doi.org/10.1016/j.rechem.2021.100102
  14. Zirconium-containing metal organic frameworks as solid acid catalysts for the N-formylation of aniline with formic acid vol.133, pp.1, 2021, https://doi.org/10.1007/s11144-021-01982-1