IBX amides: A new family of hypervalent iodine reagents

Angewandte Chemie - International Edition

Volumn 42, Issue 19, 2003, Pages 2194-2196

  Zhdankin, Viktor V ^a   Koposov, Alexey Y ^a   Netzel, Brian C ^a   Yashin, Nikolai V ^a   Rempel, Brian P ^b   Ferguson, Michael J ^b   Tykwinski, Rik R ^b  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Alcohols; Hypervalent compounds; Iodine; Oxidation; Synthetic methods

Indexed keywords

ALCOHOLS; CHEMICAL REACTIONS; CRYSTAL STRUCTURE; IODINE; ORGANIC ACIDS; OXIDATION;

CHEMICAL REAGENTS;

POLYAMIDES;

2 IODOXYBENZAMIDE; AMIDE; BENZOIC ACID DERIVATIVE; IODINE; REAGENT; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SOLUBILITY;

ALCOHOLS; AMIDES; IODINE; IODOBENZOATES; MOLECULAR STRUCTURE;

EID: 0038583812     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351018     Document Type: Article

References (32)

1. a) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, London, 1997;
2. b) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523;
3. c) T. Wirth, Angew. Chem. 2001, 113, 2889; Angew. Chem. Int. Ed. 2001, 40, 2812;
4. c) T. Wirth, Angew. Chem. 2001, 113, 2889; Angew. Chem. Int. Ed. 2001, 40, 2812;
5. d) H. Tohma, Y. Kita, Top. Curr. Chem. 2003, 224, 209.
6. a) R. Mazitschek, M. Mulbaier, A. Giannis, Angew. Chem. 2002, 114, 4216; Angew. Chem. Int. Ed. 2002, 41, 4059;
7. a) R. Mazitschek, M. Mulbaier, A. Giannis, Angew. Chem. 2002, 114, 4216; Angew. Chem. Int. Ed. 2002, 41, 4059;
8. b) K. C. Nicolaou, T. Montagnon, P. S. Baran, Angew. Chem. 2002, 114, 1035; Angew. Chem. Int. Ed. 2002, 41, 993;
9. b) K. C. Nicolaou, T. Montagnon, P. S. Baran, Angew. Chem. 2002, 114, 1035; Angew. Chem. Int. Ed. 2002, 41, 993;
10. K. C. Nicolaou, D. L. F. Gray, T. Montagnon, S. T. Harrison, Angew. Chem. 2002, 114, 1038; Angew. Chem. Int. Ed. 2002, 41, 996;
11. K. C. Nicolaou, D. L. F. Gray, T. Montagnon, S. T. Harrison, Angew. Chem. 2002, 114, 1038; Angew. Chem. Int. Ed. 2002, 41, 996;
12. K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2245;
13. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, S. Barluenga, K. W. Hunt, R. Kranich, J. A. Vega, J. Am. Chem. Soc. 2002, 124, 2233;
14. e) K. C. Nicolaou, K. Sugita, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2221;
15. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. Sugita, J. Am. Chem. Soc. 2002, 124, 2212.
16. P. J. Stevenson, A. B. Treacy, M. Nieuwenhuyzen, J. Chem. Soc. Perkin Trans. 2 1997, 589.
17. In addition to the chirality of the amino acid derived moiety, the iodine is also a potential stereogenic center, as is seen in the solid state. As the preferred conformation/configuration about the iodonium center in solution is not known, the enantiomeric/diastereomeric relationship between 4a and 4b can not be established.
18. a) V. V. Zhdankin, A. E. Koposov, J. T. Smart, R. R. Tykwinski, R. McDonald, A. Morales-Izquierdo, J. Am. Chem. Soc. 2001, 123, 4095;
19. b V. V. Zhdankin, R. M. Arbit, B. J. Lynch, P. Kiprof, V. G. Young, J. Org. Chem. 1998, 63, 6590;
20. c) H. J. Barber, M. A. Henderson, J. Chem. Soc. C 1970, 862;
21. d) T. M. Balthazar, D. E. Godaz, B. R. Stults, J. Org. Chem. 1979, 44, 1447.
22. + (78). See Supporting Information for additional synthetic and characterization details.
23. -3. CCDC-200547 (4c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
24. V. V. Zhdankin, Rev. Heteroat. Chem. 1997, 17, 133.
25. a) N. W. Alcock, J. F. Sawyer, J. Chem. Soc. Dalton Trans. 1980, 115;
26. b) A. R. Katritzky, G. P. Savage, G. J. Palenik, K. Qian, Z. Zhang, H. D. Durst, J. Chem. Soc. Perkin Trans. 2 1990, 1657;
27. c) D. G. Naae, J. Z. Gougoutas, J. Org. Chem. 1975, 40, 2129.
28. a) D. Macikenas, E. Skrzypczak-Jankun, J. D. Protasiewicz, Angew. Chem. 2000, 112, 2063; Angew. Chem. Int. Ed. 2000, 39, 2007;
29. a) D. Macikenas, E. Skrzypczak-Jankun, J. D. Protasiewicz, Angew. Chem. 2000, 112, 2063; Angew. Chem. Int. Ed. 2000, 39, 2007;
30. b) D. Macikenas, E. Skrzypczak-Jankun, J. D. Protasiewicz, J. Am. Chem. Soc. 1999, 121, 7164;
31. c) U. H. Hirt, M. F. H. Schuster, A. N. French, O. G. Wiest, T. Wirth, Eur. J. Org. Chem. 2001, 1569;
32. d) U. H. Hirt, B. Spingler, T. Wirth, J. Org. Chem. 1998, 63, 7674.