2-Iodylbenzamide, Polymer-Bound for Oxidation

Chemfiles Volume 5 Article 11

Hypervalent iodine reagents have been extensively used in many chemical transformations, especially for mild and safe oxidation of alcohols to carbonyl compounds.1 Polymer-supported hypervalent iodine is more stable than the soluble analog, suitable for automation, and ease of reaction workup. 2-Iodylbenzamide, polymer-bound, has demonstrated reactivity for oxidations similar to polymer-bound IBX, of which it is an analogue.2,3

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Typical Experimental Procedure


2-Iodylbenzamide, polymer-bound (300 mg, 0.2 mmol) and bromobenzyl alcohol (18 mg, 0.1 mmol) are mixed and stirred in CH2Cl2 (1 mL) at room temperature for 4 h. The reaction was filtered and the resin washed with CH2Cl2 (3 × 1 mL). The combined reaction solution and washings were evaporated to dryness to give a white solid (18 mg, 100%). 1H NMR confirmed that all of the alcohol was converted to the aldehyde.

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Materials

     

References

  1. Varvoglis, A. Tetrahedron, 1997, 53. Tohma, H.; Kita, Y. Adv. Synth. Catal. 2004, 346, 111.
  2. Mubaier, M.; Giannis, A. Angew. Chem., Int. Ed. Engl. 2001, 40, 4393. Sorg, G.; Mengel, A.; Jung, G.; Rademann, J. Angew. Chem., Int. Ed. Engl. 2001, 40, 4395. Reed, N. N.; Delgado, M.; Hereford, K.; Clapham, B.; Janda, K. D. Bioorg. Med. Chem. Lett. 2002, 12, 204. Lei, Z.; Denecker, C.; Jegasothy, S.; Sherrington, D. C.; Slater, N. K. H.; Sutherland, A. J. Tetrahedron Lett. 2003, 44, 1635.
  3. Chung, W.-J.; Kim, D.-K.; Lee, Y.-S. Tetrahedron Lett. 2003, 44, 9251.

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