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Selective Reduction of Aromatic Nitriles to Aldehydes by Lithium Diisobutylpiperidinohydroaluminate (LDBPA)

  • Ha, Ji-Hyun (Department of Chemistry, Kangwon National University) ;
  • Ahn, Jin-Hee (Medicinal Science Division, Korea Research Institute of Chemical Technology) ;
  • An, Duk-Keun (Department of Chemistry, Kangwon National University)
  • Published : 2006.01.20

Abstract

Keywords

References

  1. Sodium triethoxyaluminiumhydride: Hesse, G.; Schrodel, R. Angew. Chem. 1956, 68, 438
  2. Lithium triethoxyaluminium hydride: Brown, H. C.; Schoaf, C. J.; Garg, C. P. Tetrahedron Lett. 1959, 68, 438
  3. Brown, H. C. J. Chem. Educ. 1961, 38, 173 https://doi.org/10.1021/ed038p173
  4. Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1964, 86, 1079, 1085 https://doi.org/10.1021/ja01060a024
  5. de Peretti, D.; Strzalko-Bottin, T.; Seydenpenne, J. Bull. Soc. Chim. Fr. 1974, 2925
  6. Sodium diethylaluminohydride in the presence of 2,6-di-t-butylphenoxydiethylaluminium: Yoon, N. M.; Kim, S. K.; Kyong, Y. S. Bull. Korean Chem. Soc. 1986, 7, 323
  7. Organosilicon hydride: Fry, J. L. Chem. Comm. 1974, 45. Fry, J. L.; Ott, R. A. J. Org. Chem. 1981, 46, 602 https://doi.org/10.1021/jo00316a023
  8. Thexylbromoborane- dimethyl sulfide: Cha, J. S.; Oh, S. Y.; Kim, J. E. Bull. Korean Chem. Soc. 1987, 8, 301
  9. Potassium 9-sec-amyl-9-boratabicyclo[3.3.1]nonane: Cha, J. S.; Yoon, M. S. Tetrahedron Lett. 1989, 30, 3677 https://doi.org/10.1016/S0040-4039(01)80481-0
  10. Lithium tris(dihexylamino)-aluminium hydride: Cha, J. S. Bull. Korean Chem. Soc. 1992, 13, 670
  11. Yoon, N. M.; An, D. K.; Jeong, K. H. Bull. Korean Chem. Soc. 1994, 14, 302
  12. Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk SSSR 1957, 116, 422
  13. Minato, H.; Nagasaki, T. J. Chem. Soc. [c] 1966, 1866
  14. Haeck, H. H.; Kralt, T. Rec. Trav. Chim. Pats-Bas 1966, 85, 343
  15. Miller, A. E. G.; Bliss, J. W.; Achwartzman, L. H. J. Org. Chem. 1959, 24, 627 https://doi.org/10.1021/jo01087a013
  16. Tesseire, P.; Plattier, M.; Corbier, B. Recherches 1964, 14, 44
  17. Marshall, J. A.; Andersen, N. H.; Johnson, P. C. J. Org. Chem. 1970, 35, 186 https://doi.org/10.1021/jo00826a040
  18. Stevens, R. V.; Dupree, Jr., L. E.; Loewenstein, P. L. J. Org. Chem. 1972, 37, 977 https://doi.org/10.1021/jo00972a012
  19. Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585
  20. Cha, J. S.; Kwon, O. O.; Jeoung, M. K.; Kim, E. J. Bull Korean Chem. Soc. 1994, 15, 1021
  21. N,N'- Dimethylethylenediaminoaluminium hydride: Cha, J. S.; Jang, S. H.; Kwon, S. Y. Bull. Korean Chem. Soc. 2002, 23, 1697 https://doi.org/10.5012/bkcs.2002.23.12.1697
  22. Catecholalane : Cha, J. S.; Chang, S. W.; Kwon, O. O.; Kim, J. M. Synlett 1996, 165
  23. Ahn, J. H.; Song, J. I.; Ahn, J. E.; An, D. K. Bull. Korean Chem. Soc. 2005, 26, 377 https://doi.org/10.1007/s11814-009-0063-4

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  5. Selective Reduction of Aromatic Nitriles to Aldehydes by Lithium Diisobutylpiperidinohydroaluminate (LDBPA). vol.37, pp.21, 2006, https://doi.org/10.1002/chin.200621044
  6. New Synthetic Method of Aldehydes from Tertiary Amides by Lithium Diisobutylpiperidinohydroaluminate (LDBPA) vol.27, pp.11, 2006, https://doi.org/10.5012/bkcs.2006.27.11.1913
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  10. Silver‐Sulphur Oxido‐Vanadium Cluster: A Newly Born Catalyst for Direct Reduction of Aryl Carboxylic Acids to Aldehydes via Mars and van Krevelen Mechanism vol.1, pp.13, 2006, https://doi.org/10.1002/slct.201600933
  11. Controlled Reduction of Tertiary Amides to the Corresponding Alcohols, Aldehydes, or Amines Using Dialkylboranes and Aminoborohydride Reagents vol.81, pp.9, 2006, https://doi.org/10.1021/acs.joc.6b00276
  12. Methods of Nitriles Synthesis from Amines through Oxidative Dehydrogenation vol.362, pp.19, 2020, https://doi.org/10.1002/adsc.202000635
  13. Recent developments in dehydration of primary amides to nitriles vol.7, pp.22, 2020, https://doi.org/10.1039/d0qo00843e