A New Polymer-attached Reagent for the Oxidation of Primary and Secondary Alcohols

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3781-3784

  Sourkouni Argirusi, Georgia ^b   Kirschning, Andreas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001520082     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006483t     Document Type: Article

References (39)

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16. Also the polymer-supported versions of the Swern oxidation: (a) Harris, J. M.; Liu, Y.; Chai, S.; Andrews, M. D.; Vederas, J. C. J. Org. Chem. 1998, 63, 2407-2409.
17. (b) Liu, Y.; Vederas, J. C. J. Org. Chem. 1996, 61, 7856-7859. In addition, the Corey oxidation:
18. (c) Crosby, G. A.; Weinshenker, N. M.; Uh, H.-S. J. Am. Chem. Soc. 1975, 97, 2232-2235.
19. Rychnovsky, S. D.; Vaidyanathan, R. J. Org. Chem. 1999, 64, 310-312.
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24. Espenson, J. H.; Zhu, Z.; Zauche, T. H. J. Org. Chem. 1999, 64, 1191-1196.
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26. (b) De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piacantelli, G. J. Org. Chem. 1997, 62, 6974-6977.
27. Preparation of reagent 1 was achieved by oxidative, iodine(III)-promoted ligand transfer onto polystyrene-bound bromide: Monenschein, H.; Sourkouni-Argirusi, G.; Schubothe, K. M.; O'Hare, T.; Kirschning, A. Org. Lett. 1999, 1, 2101-2104.
28. (a) Kirschning, A.; Monenschein, H.; Schmeck, C. Angew. Chem. 1999, 111, 2720-2722; Angew. Chem., Int. Ed. 1999, 38, 2594-2596.
29. (a) Kirschning, A.; Monenschein, H.; Schmeck, C. Angew. Chem. 1999, 111, 2720-2722; Angew. Chem., Int. Ed. 1999, 38, 2594-2596.
30. (b) Kirschning, A.; Jesberger, M.; Moneneschein, H. Tetrahedron Lett. 1999, 40, 8999-9002.
31. Polymer-bound bromide was purchased from Fluka (3.5 mmol/g bromide). Polymer-bound reagent 1 is also available from Novabiochem (Switzerland).
32. The need for an excess of 1 may be rationalized by assuming that only a proportional amount of immobilized halide was transformed into the hypervalent species or that only the most accessible haloate(I) anions are involved in the cohalogenation process. A 3-fold excess was sufficient in most cases but led to considerably longer reaction times as was shown by a series of oxidations of alcohol 8 to benzaldehyde 15 under varying conditions (equiv of 1, reaction time; % transformation to 15): 1, 24 h, 34%; 2, 24 h, 69%; 3, 24 h, >95%; 4, 2 h, >95%; 5, 1 h, >95%; 6, 30 min, >95%.
33. (a) Kirschning, A.; Dräger, G.; Jung, A. Angew. Chem. 1997, 109, 253-255; Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255.
34. (a) Kirschning, A.; Dräger, G.; Jung, A. Angew. Chem. 1997, 109, 253-255; Angew. Chem., Int. Ed. Engl. 1997, 36, 253-255.
35. (b) Monenschein, H.; Dräger, G.; Jung, A.; Kirschning, A. Chem. Eur. J. 1999, 5, 2270-2280.
36. Polymer-bound DMSO useful for the Swern oxidation may only be prepared via multistep solid-phase synthesis. Furthermore, compared to reagent 1 it is less easily recycled (refer to refs 9a and 9b).
37. In our hands the chromium-based reagents 3 and 4 show the tendency of over-oxidation of primary alcohols.
38. Hashem, Md. A.; Jung, A.; Ries, M.; Kirschning, A. Synlett 1998, 195-197.
39. The polymer-bound iodine-containing analogue of reagent 1 is also able to promote these kinds of oxidations. However, in part iodine is released into solution during the process, which can lead to byproducts.