Hypervalent iodine catalyzed hofmann rearrangement of carboxamides using oxone as terminal oxidant

Journal of Organic Chemistry

Volumn 77, Issue 24, 2012, Pages 11399-11404

  Yoshimura, Akira ^a   Middleton, Kyle R ^a   Luedtke, Matthew W ^a   Zhu, Chenjie ^a   Zhdankin, Viktor V ^a  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS METHANOL SOLUTIONS; CARBOXAMIDES; CATALYTIC AMOUNTS; HIGH YIELD; HOFMANN REARRANGEMENT; HYPERVALENT IODINE; IODOBENZENE; TERMINAL OXIDANTS;

CATALYSIS; ORGANIC COMPOUNDS; OXIDANTS;

IODINE;

1,1,1,3,3,3 HEXAFLUOROISOPROPANOL; 2 (2 CHLOROPHENYL)ACETAMIDE; 2 (3 CHLOROPHENYL)ACETAMIDE; 2 (4 BROMOPHENYL)ACETAMIDE; 2 (4 CHLOROPHENYL)ACETAMIDE; 2 (4 FLUOROPHENYL)ACETAMIDE; 2 [(4 TRIFLUOROMETHYL)PHENYL]ACETAMIDE; 2 METHYLHEXANAMIDE; 2,2 DIMETHYLHEXANAMIDE; 5 PHENYLPENTANAMIDE; 6 PHENYLHEXANAMIDE; 7 BROMOHEPTANAMIDE; 7 CHLOROHEPTANAMIDE; AMIDE; BICYCLO[2.2.1]HEPTANE 2 CARBOXAMIDE; CARBAMIC ACID; CYCLOPENTANECARBOXAMIDE; IODINE; IODOBENZENE; METHANOL; METHYL N (2 CHLOROBENZYL)CARBAMATE; METHYL N (3 CHLOROBENZYL)CARBAMATE; METHYL N (4 BROMOBENZYL)CARBAMATE; METHYL N (4 CHLOROBENZYL)CARBAMATE; METHYL N (4 FLUOROBENZYL)CARBAMATE; METHYL N (4 METHYLBENZYL)CARBAMATE; METHYL N BENZYLCARBAMATE; OCTANAMIDE; PROPANOL; SODIUM PEROXIDE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; HOFFMANN REARRANGEMENT; LIGAND BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STOICHIOMETRY; SUBSTITUTION REACTION;

EID: 84871589464     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302375m     Document Type: Article

References (49)

1. Hypervalent Iodine Chemistry; Wirth, T., Ed.; Springer-Verlag: Berlin, 2003.
2. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299-5358
3. Dohi, T.; Kita, Y. Chem. Commun. 2009, 2073-2085
4. Ochiai, M.; Miyamoto, K. Eur. J. Org. Chem. 2008, 4229-4239
5. Uyanik, M.; Ishihara, K. Chem. Commun. 2009, 2086-2099
6. Zhdankin, V. V. J. Org. Chem. 2011, 76, 1185-1197
7. Moriarty, R. M.; Chany, C. J., II; Vaid, R. K.; Prakash, O.; Tuladhar, S. M. J. Org. Chem. 1993, 58, 2478-2482
8. Okamoto, N.; Miwa, Y.; Minami, H.; Takeda, K.; Yanada, R. Angew. Chem., Int. Ed. 2009, 48, 9693-9696
9. Loudon, G. M.; Radhakrishna, A. S.; Almond, M. R.; Blodgett, J. K.; Boutin, R. H. J. Org. Chem. 1984, 49, 4272-4276
10. Boutin, R. H.; Loudon, G. M. J. Org. Chem. 1984, 49, 4277-4284
11. Lazbin, I. M.; Koser, G. F. J. Org. Chem. 1986, 51, 2669-2671
12. Moriarty, R. M.; Enache, L. A.; Zhao, L.; Gilardi, R.; Mattson, M. V.; Prakash, O. J. Med. Chem. 1998, 41, 468-477
13. Yoshimura, A.; Luedtke, M. W.; Zhdankin., V. V. J. Org. Chem. 2012, 77, 2087-2091
14. Tohma, H.; Maruyama, A.; Maeda, A.; Maegawa, T.; Dohi, T.; Shiro, M.; Morita, T.; Kita, Y. Angew. Chem., Int. Ed. 2004, 43, 3595-3598
15. Yusubov, M. S.; Funk, T. V.; Chi, K.-W.; Cha, E.-H.; Kim, G. H.; Kirschning, A.; Zhdankin, V. V. J. Org. Chem. 2008, 73, 295-297
16. Zagulyaeva, A. A.; Banek, C. T.; Yusubov, M. S.; Zhdankin, V. V. Org. Lett. 2010, 12, 4644-4647
17. Moriyama, K.; Ishida, K.; Togo, H. Org. Lett. 2012, 14, 946-949
18. Miyamoto, K.; Sakai, Y.; Goda, S.; Ochiai, M. Chem. Commun. 2012, 48, 982-984
19. Yusubov, M. S.; Zagulyaeva, A. A.; Zhdankin, V. V. Chem.-Eur. J. 2009, 15, 11091-11094
20. Zagulyaeva, A. A.; Yusubov, M. S.; Zhdankin, V. V. J. Org. Chem. 2010, 75, 2119-2122
21. Yoshimura, A.; Neu, H. M.; Nemykin, V. N.; Zhdankin, V. V. Adv. Synth. Catal. 2010, 352, 1455-1460
22. Yusubov, M. S.; Nemykin, V. N.; Zhdankin, V. V. Tetrahedron 2010, 66, 5745-5752
23. Thottumkara, A. P.; Bowsher, M. S.; Vinod, T. K. Org. Lett. 2005, 7, 2933-2936
24. Uyanik, M.; Akakura, M.; Ishihara, K. J. Am. Chem. Soc. 2009, 131, 251-262
25. Thottumkara, A. P.; Vinod, T. K. Org. Lett. 2010, 12, 5640-5643
26. Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684-3691
27. Miyamoto, K.; Tada, N.; Ochiai, M. J. Am. Chem. Soc. 2007, 129, 2772-2773
28. Dohi, T.; Yamaoka, N.; Kita, Y. Tetrahedron 2010, 66, 5775-5785
29. Hamdouchi, C.; Sanchez-Martinez, C.; Gruber, J.; del Prado, M.; Lopez, J.; Rubio, A.; Heinz, B. A. J. Med. Chem. 2003, 46, 4333-4341
30. Andrews, P. A.; Brinkworth, R. I.; Partridge, A. C.; Reiss, J. A. Aust. J. Chem. 1988, 41, 1717-1725
31. Tanaka, K.; Yoshifuji, S.; Nitta, Y. Chem. Pharm. Bull. 1988, 36, 3125-3129
32. Reid, E. B.; Ruby, W. R. J. Am. Chem. Soc. 1951, 73, 1054-1061
33. Wenkert, E.; Barnett, B. F. J. Am. Chem. Soc. 1960, 82, 4671-4675
34. Nathan, A.; Alexandra, J. P.; Jonathan, M. J. W. Org. Lett. 2007, 9, 3599-3601
35. Nesmeyanov, A. N.; Zakharkin, L. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1955, 224-232
36. Durand, P.; Richard, P.; Renaut, P. J. Org. Chem. 1998, 63, 9723-9727
37. Goerner, L. G.; Holzschuh, A. A. J. Org. Chem. 1958, 23, 1346-1349
38. Mcelvain, S. M.; Aldridge, C. L. J. Am. Chem. Soc. 1953, 75, 3987-3993
39. Bonne, D.; Dekhane, M.; Zhu, J. J. Am. Chem. Soc. 2005, 127, 6926-6927
40. Leathen, M. L.; Peterson, E. A. Tetrahedron Lett. 2010, 51, 2888-2891
41. Song, H. B.; Choi, M. H.; Koo, I. S.; Oh, H. K.; Lee, I. Bull. Korean Chem. Soc. 2003, 24, 91-94
42. Clarke, C. T.; Elliott, J. D.; Jones, J. H. J. Chem. Soc., Perkin Trans. 1 1978, 1088-1090
43. Ito, Y.; Ushitora, H. Tetrahedron 2006, 62, 226-235
44. Dicks, P. F.; Glover, S. A.; Goosen, A.; McCleland, C. W. Tetrahedron 1987, 43, 923-934
45. Hiegel, G. A.; Hogenauer, T. J. Synth. Commun. 2005, 35, 2091-2098
46. Badamshina, E. R.; Grigorieva, V. A.; Komratova, V. V.; Ol'khov, Y. A.; Lodygina, V. P.; Gorbushina, G. A.; Baturin, S. M. Intern. J. Polym. Mater. 1993, 19, 117-125
47. Daniel, B.; Jean-Claude, B.; Gabriele, F.; Martin, K.; Franz, K.; Markm, P.; Marcel, V. Eur. Pat. Appl. 2002, EP 1245558 A1 20021002.
48. Guin, J.; Muck-Lichtenfeld, C.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2007, 129, 4498-4503
49. Kirmse, W.; Siegfried, R. J. Am. Chem. Soc. 1983, 105, 950-956