Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Facile Reduction of Carboxylic Acid Salts to Aldehydes by Boron Hydrides Thexylbromoborane-Dimethyl Sulfide and 9-Borabicyclo [3.3.1]nonane

  • Published : 1988.12.20
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Abstract

New methods of the reduction of carboxylic acid salts to aldehydes with 2 equiv of thexylbromoborane-dimethyl sulfide (ThxBHBr${\cdot}SMe_2$) or 9-borabicyclo[3.3.1]nonane (9-BBN) are described. Both these reagents provide the corresponding aldehydes from various as sodium and lithium salts of carboxylic acids in high yields both at room temperature. Such facile reductions are explained as the simple substitution for the bromo group of ThxBHBr by a carboxylate to form thexyl(acyloxty)borane followed by reduction with excess reagent and the formation of an ate complex followed by reduction with excess 9-BBN.

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References

  1. Compendium of Organic Synthetic Methods v.1 I. T. Harrison;S. Harrison
  2. Compendium of Organic Synthetic Methods v.3 I. T. Harrison;S. Harrison
  3. Org. Reac. v.8 E. Mosettig
  4. Ber. v.51 K. W. Rosenmund
  5. Org. Reac. v.4 E. Mosettig
  6. Recl. Trav. Chim. Pays-Bas. v.90 J. A. Peters;H. van Bekkum
  7. Recl. Trav. Chim. Pays-Bas. v.100 J. A. Peters;H. van Bekkum
  8. J. Org. Chem. v.34 J. D. Citron
  9. Chem. Commun. S. P. Dent;C. Eaborn;A. Pidcock
  10. J. Chem. Soc. H. Stephen
  11. J. Am. Chem. Soc. v.69 A. E. Finholt;A. C. Bond, Jr.;H. I. Schlesinger
  12. Tetrahedron v.35 H. C. Brown
  13. Angew. Chem. v.64 F. Weygand;G. Eberhardt
  14. J. Am. Chem. Soc. v.83 H. C. Brown;A. Tsukamoto
  15. Tetrahedron Lett. L. I. Zakharkin;I. M. Khorlina
  16. J. Org. Chem. v.31 P. M. Weissman;H. C. Brown
  17. J. Am. Chem. Soc. v.86 H. C. Brown;A. Tsukamoto
  18. J. Am. Chem. Soc. v.80 H. C. Brown;B. C. Subba Rao
  19. Tetrahedron Lett. H. C. Brown;C. J. Shoaf;C. P. Garg
  20. J. Am. Chem. Soc. v.86 H. C. Brown;C. P. Garg
  21. Bull. Chem. Soc. Jpn. v.52 T. Izawa;T. Mukaiyama
  22. J. Chem. Soc., Perkin Trans. v.1 I. D. Entwistle;P. Boehm;R. A. W. Johnstone;R. P. Telford
  23. Chem. Lett. M. Mukai;Mukaiyama
  24. Tetrahedron Lett. R. O. Hutchins;M. Markowitz
  25. Tetrahedron Lett. J. H. Babler;B. J. Invergo
  26. Tetrahedron Lett. L. I. Zakharkin;V. V. Gayrilenko;D. N. Maslin;I. M. Khorlina
  27. Tetrahedron Lett. T. E. Cole;R. Petit
  28. J. Org. Chem. v.52 J. S. Cha;J. E. Kim;K. W. Lee
  29. Tetrahedron Lett. v.28 J. S. Cha;J. E. Kim;S. Y. Oh;J. C. Lee;K. W. Lee
  30. Tetrahedron Lett. v.28 J. S. Cha;J. E. Kim;S. Y. Oh;J. D. Kim
  31. Tetrahedron Lett. v.28 J. S. Cha;J. E. Kim;M. S. Yoon;Y. S. Kim
  32. Bull. Korean Chem. Soc. v.9 J. S. Cha;S. Y. Oh;K. W. Lee;M. S. Yoon;J. C. Lee;J. E. Kim
  33. Heterocycles v.27 J. S. Cha;S. Y. Oh;K. W. Lee;M. S. Yoon;J. C. Lee;J. E. Kim
  34. Bull. Korean Chem. Soc. v.8 J. S. Cha;S. Y. Oh;J. E. Kim
  35. Bull. Korean Chem. Soc. v.8 J. S. Cha;S. Y. Oh;J. E. Kim
  36. Z. Naturforsch. B: Anorg. Chem. Org. Chem. v.30B K. Kinberger;W. Siebert
  37. J. Org. Chem. v.41 H. C. Brown;S. Krishnamurthy;N. M. Yoon
  38. J. Am. Chem. Soc. v.106 H. C. Brown;J. S. Cha;B. Nazer;N. M. Yoon
  39. J. Org. Chem. v.52 H. C. Brown;J. S. Cha;N. M. Yoon;B. Nazer
  40. Organic Syntheses via Boranes H. C. Brown;G. W. Kramer;A. B. Levy;M. M. Midland

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  2. Conversion of Carboxylic Acids to Aldehydes with Cyclic Dialkyldiaminoaluminum Hydrides vol.23, pp.9, 1988, https://doi.org/10.5012/bkcs.2002.23.9.1340
  3. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1988, https://doi.org/10.5012/bkcs.2011.32.6.1808
  4. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1988, https://doi.org/10.5012/bkcs.2011.32.6.1808
  5. Some Recommended Procedures for Conversion of Carboxylic Acid and Its Derivatives to Aldehydes by Metal Hydride Reductions vol.5, pp.2, 2012, https://doi.org/10.13160/ricns.2012.5.2.084
  6. Some Recommended Procedures for Conversion of Carboxylic Acid and Its Derivatives to Aldehydes by Metal Hydride Reductions vol.5, pp.2, 2012, https://doi.org/10.13160/ricns.2012.5.2.084