Benzylic carbon oxidation by an in situ formed o-iodoxybenzoic acid (IBX) derivative

Synlett

Volumn , Issue 1, 2009, Pages 117-121

  Ojha, Lawanya R ^a   Kudugunti, Shashi ^a   Maddukuri, Padma P ^a   Kommareddy, Amitha ^a   Gunna, Meena R ^a   Dokuparthi, Praveen ^a   Gottam, Hima B ^a   Botha, Kiran K ^a   Parapati, Divya R ^a   Vinod, Thottumkara K ^a  

^a WESTERN ILLINOIS UNIVERSITY   (United States)

Author keywords

o iodoxybenzoic acid (IBX); Oxidation; Oxone ; Rearrangement; Single electron transfer

Indexed keywords

EID: 62349130571     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087384     Document Type: Article

References (37)

1. (a) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidation of Organic Compounds; Academic: New York, 1981.
2. (b) Sheldon, R. A.; Kochi, J. K. Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley-Interscience: New York, 1989.
3. (c) The Activation of Dioxygen and Homogeneous Catalytic Oxidations; Barton, D. H. R.; Martell, A. E.; Sawyer, D. T., Eds.; Plenum Press: New York, 1993.
4. (d) Shilov, A. E.; Shulpin, G. B. Chem. Rev. 1997, 97, 2879.
5. (a) Muzart, J. Chem. Rev. 1992, 92, 113.
6. (b) Sasson, Y.; Zippi, G. D.; Neumann, R. J. Org. Chem. 1986, 51, 2880.
7. (c) Yoshino, Y.; Hayashi, Y.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1997, 62, 6810.
8. (d) Yamazaki, S. Org. Lett. 1999, 1, 2129.
9. (e) Khenkin, A. M.; Neumann, R. J. Am. Chem. Soc. 2001, 124, 4198.
10. (f) Catino, A. J.; Nichols, J. M.; Choi, H.; Gottipamula, S.; Doyle, M. P. Org. Lett. 2005, 7, 5167.
11. (g) Yang, D.; Wong, M.-K.; Wang, X.-C.; Tang, Y.-C. J. Am. Chem. Soc. 1998, 120, 6611.
12. (h) Bonvin, Y.; Callens, E.; Larrossa, I.; Henderson, D.; Oldham, J.; Burton, A. J.; Barrett, A. G. M. Org. Lett. 2005, 7, 4549.
13. (i) Lenoir, D. Angew. Chem. Int. Ed. 2006, 45, 3206.
14. (a) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245.
15. (b) Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem. Int. Ed. 2002, 41, 993.
16. (c) Nicolaou, K. C.; Gray, D. L. F.; Montagnon, T.; Harrison, S. F. Angew. Chem. Int. Ed. 2002, 41, 996.
17. (d) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5182.
18. (e) Kirsch, S. F. J. Org. Chem. 2005, 70, 10210.
19. (f) Moorthy, J. N.; Singhal, N.; Senapati, K. Tetrahedron Lett. 2006, 47, 1757.
20. Caution! IBX is known to explode upon impact or heating at >200°C, see: Plumb, J. B.; Harper, D. J. Chem. Eng. News 1990, 68 (July 16), 3.
21. (a) Thottumkara, A. P.; Vinod, T. K. Tetrahedron Lett. 2002, 43, 569.
22. (b) Kommareddy, A.; Bowsher, M. S.; Gunna, M. R.; Botha, K.; Vinod, T. K. Tetrahedron Lett. 2008, 49, 4378.
23. (c) Richardson, R. R.; Zayed, J. M.; Altermann, S.; Smith, D.; Wirth, T. Angew. Chem. Int. Ed. 2007, 46, 6529.
24. (d) Finney, J. S.; Moore, N. S. Org. Lett. 2002, 4, 3001.
25. Thottumkara, A. P.; Bowsher, M. S.; Vinod, T. K. Org. Lett. 2005, 7, 2933.
26. (a) Page, P. C. B.; Appleby, L. F.; Buckley, B. R.; Allin, S. M.; McKenzie, M. J. Synlett 2007, 1565.
27. (b) Richardson, R. D.; Wirth, T. Angew. Chem. Int. Ed. 2006, 45, 4402.
28. Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901.
29. 4. For the use of Oxone® for the oxidation of 2IBAcid to IBX, see: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537.
30. Meyer, J. M. Acc. Chem. Res. 1998, 31, 441; and references cited therein.
31. We arrived at this compensation by estimating the amount of Oxone® remaining after heating a solution of Oxone® in the solvent mixture employed for the reaction for 48 h. We used the Dupont® reported iodometric procedure for the estimation of Oxone® available at: http://www.dupont.com/ oxone/techinfo/index.html (accessed May 2008).
32. (a) Criegee, R. Ber. Dtsch. Chem. Ges. B 1944, 77, 722.
33. (b) Olah, G. A.; Parker, D. G.; Yoneda, N. Angew. Chem., Int. Ed. Engl. 1978, 17, 909.
34. (c) Krasutsky, P. A.; Kolomitsyn, I. V.; Krasutsky, S. G.; Kiprof, P. Org. Lett. 2004, 6, 2539.
35. (a) Travis, B. R.; Sivakumar, M.; Hollist, O.; Borhan, B. Org. Lett. 2003, 50, 1031.
36. (b) Gandhari, R.; Maddukuri, P. P.; Vinod, T. K. J. Chem. Educ. 2007, 84, 852.
37. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.