Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

New Route to N-Formylation of Primary Amines with Amino Acids as a Source of CO Using Polyaniline Catalyst

  • Published : 2009.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

The treatment of primary amines with amino acids as a CO source in the presence of polyaniline emeraldine salts bring about N-formylation to give the corresponding formamides. This route to N-formylation methodology of primary amine represents the first reported example of a CO-transfer via radical mechanism by highly nanoporous polyaniline emeraldine salts catalyst.

Keywords

References

  1. Gattermann, L.; Koch, J. A. Chem. Ber. 1987, 30, 1622.
  2. Olha, G. A. Friedel-Crafts and Related Reaction; Wiley-Interscience: New York, 1964; Vol. III, p 1153.
  3. Olha, G. A.; Farooq, O.; Marcelli, M.; Prakash, G. K. S. J. Am. Chem. Soc. 1988, 110, 864. https://doi.org/10.1021/ja00211a027
  4. Olha, G. A.; Prakash, G. K. S.; Mathew, T.; Marinez, E. Angew. Chem. 2000, 112, 2647. https://doi.org/10.1002/1521-3757(20000717)112:14<2647::AID-ANGE2647>3.0.CO;2-A
  5. Blicker, F. F.; Lu, C.-J. J. Am. Chem. Soc. 1952, 74, 3933. https://doi.org/10.1021/ja01135a503
  6. Waki, J.; Meienhofer, J. J. Org. Chem. 1977, 42, 2019. https://doi.org/10.1021/jo00431a046
  7. 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
  8. Zhang, Y.; Desharnais, J.; Greasley, S. E.; Beardsley, G. P.; Boger, D. L.; Wilson, I. A. Biochemistry 2002, 41, 14206. https://doi.org/10.1021/bi020522m
  9. Onel, L.; Wittmann, M.; Pelle, K.; Noszticzius, Z.; Sciascia, L. J. Phys. Chem. A 2007, 111, 7805. https://doi.org/10.1021/jp073512+
  10. MacDiarmid, A. G. Synth. Met. 2001, 125, 11. https://doi.org/10.1016/S0379-6779(01)00508-2
  11. Cao, Y.; Heeger, A. J. Synth. Met. 1992, 52, 193 https://doi.org/10.1016/0379-6779(92)90307-5
  12. Hirao, T.; Higuchi, M.; Iketa, I.; Ohshiro, Y. J. Chem., Chem. Commun. 1993, 194.
  13. Lee, S. H.; Lee, D. H.; Lee, K. H.; Lee, C. W. Adv. Funct. Mater. 2005, 15, 1495. https://doi.org/10.1002/adfm.200400467
  14. Lee, K. H.; Cho, S. U.; Park, S. H.; Heeger, A. J.; Lee, C. W. Nature 2006, 441, 65. https://doi.org/10.1002/adfm.200400467
  15. Chi, K. W.; Hwang, H. Y.; Ryu, K. S.; Kim, J. M.; Yoon, U. C.; Lee, C. W. Bull. Korean Chem. Soc. 2009, 30, 1245. https://doi.org/10.1038/nature04705
  16. Huang, J.; Kaner, R. B. J. Am. Chem. Soc. 2004, 126, 851. https://doi.org/10.1021/ja0371754
  17. Huang, J.; Kaner, R. B. Angew. Chem. Int. Ed. 2004, 43, 5817. https://doi.org/10.1021/ja0371754
  18. Chi, K. W.; Hwang, H. Y.; Park, J. Y.; Lee, C. W. Synth. Met. 2009, 159, 26. https://doi.org/10.1002/anie.200460616
  19. Lee, C. W.; Hwang, H. Y.; Jung, H. M. Chi, K.-W. Synth. Met. 2009, in press.
  20. Reddy, S. R.; Das, S.; Punniyamurthy, T. Tetrahedron Lett. 2004, 45, 3561. https://doi.org/10.1016/j.tetlet.2004.03.056
  21. Velusamy, S.; Ahamed, M.; Punniyamurthy, T. Organic Lett. 2004, 6, 4821. https://doi.org/10.1016/j.tetlet.2004.03.056
  22. Kantam, M. L.; Roy, M.; Roy, S.; Sreedhar, B.; De, R. L. Catalysis Commun. 2008, 9, 2226. https://doi.org/10.1021/ol048195t

Cited by

  1. Transformylating amine with DMF to formamide over CeO2 catalyst vol.50, pp.19, 2014, https://doi.org/10.1039/c3cc48400a
  2. -formylation of various amines and its biological activity studies vol.31, pp.12, 2017, https://doi.org/10.1002/aoc.3874
  3. Controlled modification of biomolecules by ultrashort laser pulses in polar liquids vol.7, pp.1, 2017, https://doi.org/10.1038/s41598-017-05761-8
  4. ChemInform Abstract: New Route to N-Formylation of Primary Amines with Amino Acids as a Source of CO Using Polyaniline Catalyst. vol.41, pp.12, 2010, https://doi.org/10.1002/chin.201012062