Polymer-Supported Reducing Reagents

Chemfiles Volume 4 Article 1

Borohydride, polymer-supported on Amberlite IRA-400


Polymer-supported reducing agent possessing greater selectivity than the corresponding alkali borohydrides.1 This versatile resin has been shown to effectively reduce α-β unsaturated carbonyl compounds to the corresponding unsaturated alcohols;2 olefinic bonds,3 aryl azides and arylsulfonyl azides to the corresponding aromatic amines and aryl sulfonamides using MeOH as solvent;4 α-β unsaturated nitroalkenes to nitroalkanes;5 aromatic oximes to the corresponding amines;6 and aldehydes and ketones to the corresponding alcohols.7

Borohydride, polymer-supported on Amberlite A-26


Cyanoborohydride, polymer-supported


Polymer-supported reducing agent used in reductive amination reactions at room temperature.8 This resin was utilized with polymer-supported perruthenate (51,158-7 p.5) in oxidative-reductive amination reactions to convert alcohols to amines.9 It was also employed in the preparation of piperidino-thiomorpholine libraries via reductive amination of ketones.10

Tributyltin fluoride, polymer-bound


Reagent for the selective desilylation of bis(silyl)enol ethers

Zinc borohydride, polymer-bound


Used to the chemoselective reduction of aldehydes in the presence of ketones.

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Materials

     

References

  1. Gibson, H.W.; Bailey, J. J. Chem. Soc. Chem Comm. 1997, 815.
  2. Sande, A.R. et al. Tetrahedron Lett. 1984, 25, 3501.
  3. Nag, A. et al. Synth. Commun. 1987, 17, 1007.
  4. Kabalka, G.W. et al. ibid. 1990, 20, 293.
  5. Goudgaon, N.M. et al. ibid. 1989, 805.
  6. Bandgar, B.P. et al. ibid. 1995, 25, 863.
  7. Yoon, N.M. et al. Tetrahedron Lett. 1983, 24, 5367.
  8. Hutchins, R.O. et al. J. Chem. Soc. Chem. Commun. 1978, 1088.
  9. Ley, S.V. et al. J. Chem. Soc. Perkin Trans. I 1998, 2239.
  10. Habermann, J. et al. J. Chem. Soc. Perkin Trans. I 1998, 3127.
  11. Urabe, H.; Kuwajima, I. et al. Tetrahedron Lett. 1983, 24, 5001.
  12. Firouzabadi, H.; Tamami, B. Synth. Comm. 1991, 21, 2275-2285.

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