Iron-catalyzed oxidation of thioethers by iodosylarenes: Stereoselectivity and reaction mechanism

Chemistry - A European Journal

Volumn 13, Issue 28, 2007, Pages 8045-8050

  Bryliakov, Konstantin P ^a   Talsi, Evgenii P ^a  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

Author keywords

Asymmetric; Catalysis; Iron; Oxidation; Reaction mechanisms; Sulfoxides

Indexed keywords

CATALYST ACTIVITY; ENANTIOSELECTIVITY; LIGANDS; OXIDANTS; OXIDATION; REACTION KINETICS; STEREOSELECTIVITY;

ALKYL ARYL SULFIDES; SULFOXIDATION; SULFOXIDES;

ETHERS;

EID: 35048854604     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700566     Document Type: Article

References (60)

1. a) Catalytic Asymmetric Synthesis, 2nd ed. (Ed. I. Ojima) Wiley, New York, 2000;
2. b) Comprehensive Asymmetric Catalysis (Eds.: E.N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
3. c) In 2006 the global sales of chiral drugs atorvastatine (Lipitor™) and (S)-omeprazole (Nexium™) amounted to $11,7 billion (http:// www.imshealth.com) and $4.1 billion. (http://www.drugpatentwatch.com), respectively.
4. a) J. Legros, J. R. Dehli, C. Bolm, Adv. Synth. Catal. 2005, 347, 19-31;
5. b) I. Fernandez, N. Khiar, Chem. Rev. 2003, 103, 3651-3706;
6. c) H.-J. Federsel, Chirality 2003, 15, S128-S142.
7. a) P. Pitchen, H. B. Kagan, Tetrahedron Lett. 1984, 25, 1049-1052;
8. b) P. Pitchen, M. Desmukh, E. Dunach. H. B. Kagan, J. Am. Chem. Soc. 1984, 106, 8188-8193;
9. c) F. Di Furia, G. Modena, R. Seraglia, Synthesis 1984, 325-326.
10. C. Bolm, J. Legros, J. Le Paih, L. Zani. Chem. Rev. 2004, 104, 6217-6254.
11. a) J. T. Groves. P. J. Viski, J. Org. Chem. 1990, 55, 3628-3634;
12. b) Y. Naruta, F. Tani, K. Maruyama, J. Chem. Soc. Chem. Commun. 1990, 1378-1380;
13. c) Y. Naruta, F. Tani, K. Maruyama, Tetrahedron: Asymmetry 1991, 2, 533-542;
14. d) L.-C. Chiang, K. Konishi, T. Aida, S. Inoue, J. Chem. Soc. Chem. Commun. 1992, 254-256;
15. e) Q. L. Zhou, K. C. Chen. Z. H. Zhu, J. Mol. Catal. 1992, 72, 59-65;
16. f) C. Duboc-Toia, S. Menage, C. Lambeaux, M. Fontecave, Tetrahedron Lett. 1997, 35, 3727-3730;
17. g) C. Duboc-Toia, S. Menage, R. Y. Ho, L. Que, Jr., C. Lambeaux, M. Fontecave, Inorg. Chem. 1999, 38, 1261-1268;
18. h) Y. Mekmouche, H. Hummel, R.Y.N. Ho, L. Que, Jr., V. Schünemann, F. Thomas, A. X. Trautwein, C. Lebrun, K. Gorgy, J.-C. Leprêtre, M.-N. Collomb, A. Deronzier, M. Fontecave, S. Menage, Chem. Eur. J. 2002, 8, 1196-1204.
19. a) J. Legros, C. Bolm, Angew. Chem. 2003, 115, 5645-5647;
20. Angew. Chem. Int. Ed. 2003, 42, 5487-5489;
21. b) J. Legros, C. Bolm, Angew. Chem. 2004, 116, 4321-4324;
22. Angew. Chem. Int. Ed. 2004, 43, 4225-4228;
23. c) J. Legros, C. Bolm, Chem. Eur. J. 2005, 11, 1086-1092;
24. d) A. Korte, J. Legros, C. Bolm, C. Synlett. 2004, 13, 2397-2399.
25. a) V. K. Sivasubramanian, M. Ganesan, S. Rajagopal, R. Ramaraj, J. Org. Chem. 2002, 67, 1506-1514;
26. b) K. P. Bryliakov, E. P. Talsi, Angew. Chem. 2004, 116, 5340-5342;
27. Angew. Chem. Int. Ed. 2004, 43, 5228-5230.
28. a) W.-H. Leung, E. Y. Y. Chan, E. K. F. Chow, I. D. Williams, S.-M. Peng, J. Chem. Soc Dalton Trans. 1996, 1229-1236;
29. b) T. Liu, Q.-X. Liu, W.-H. R-an, Z.-A. Zhu, Y-T. Chen, A. S. C. Chan, Chin. J. Chem. 2001, 19, 352-355;
30. c) S. K. Edulji. S. T. Nguyen, Organometallics 2003, 22, 3374-3381.
31. a) A. X. Trautwein, E. Bill, E. L. Bominaar, H. Winkler, Struct. Bonding 1998, 75, 1-95;
32. b) K. Jayaraj, J. Terner, A. Gold, D. A. Roberts, R. N. Austin, D. Mandón, R. Weiss, E. Bill, M. Muther, A. X. Trautwein, Inorg. Chem. 1996, 35, 1632-1640;
33. c) D. Mandon, P. Ochsenbein, J. Fischer, R. Weiss, K. Jayaraj, R. N. Austin, A. Gold, P. S. White, O. Brigaud, P. Battioni, D. Mansuy, Inorg. Chem. 1992, 31, 4404-4409;
34. d) W. Nam, S. K. Choi, M. H. Lim, J.-U. Rohde, I. Kim, J. Kim, C. Kim, L. Que, Angew. Chem. 2003, 115, 113-115;
35. Angew. Chem. Int. Ed. 2003, 42, 109-111;
36. e) W. J. Song, Y J. Sun, S. K. Choi, W. Nam, Chem. Eur. J. 2006, 12, 130-137.
37. a) J. P. Coliman, A. S. Chien, T. A. Eberspacher, J. I. Brauman, J. Am. Chem. Soc. 2000, 122, 11098-11100;
38. b) J. P. Coliman, L. Zeng, R. A. Decréau, Chem. Commun. 2003, 2974-2975;
39. c) Y. Yang, F. Diederich, J. S. Valentine, J. Am. Chem. Soc. 1990, 112, 7826-7828;
40. d) S. H. Wang, B. S. Mandimutsira, R. Todd, B. Ramdhanie, J. P. Fox, D. P. Goldberg, J. Am. Chem. Soc. 2004, 126, 18-19;
41. J. P. Collman, L. Zeng, J. I. Brauman, Inorg. Chem. 2004, 43, 2672-2679.
42. 1H NMR spectroscopic monitoring of p-BrPhSMe oxidation with PhIO catalyzed by 4 revealed that no decomposition of the dimeric complex to monomers was observed at least after about 10 turnovers.
43. a) H. Sasaki, R. Irie, T. Hamada, K. Suzuki, T. Katsuki, Tetrahedron 1994, 50. 11827-11838;
44. b) K.-H. Ahn, S.W. Park, S. Choi, H.-J. Kim, C. J. Moon, Tetrahedron Lett. 2001, 42, 2485-2488;
45. c) B. Saito, T. Katsuki, Tertrahedron Lett. 2001, 42, 3873-3876, and references therein.
46. a) K. P. Bryliakov, E. P. Talsi, J. Mol. Catal. A 2007, 264, 280-287;
47. b) A. Lattanzi, P. Iannece, A. Scretti, Tetrahedron: Asymmetry 2004, 15, 1779-1785;
48. c) A. Lattanzi, P. Iannece, A. Scretti, Tetrahedron: Asymmetry 2004, 15, 413-418;
49. d) A. Massa, V. Mazza, A. Scretti, Tetrahedron: Asymmetry 2005, 16, 2271-2275;
50. e) H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249-330.
51. a) P. Piaggio, P. McMorn, D. Murphy, D. Bethell, P. C. Bulman Page, F. E. Hankock, C. Sly, O. J. Kerton, G. I. Hutchings, J. Chem. Soc. Perkin Trans. 2 2000, 2008-2015;
52. b) U. H. Hirt, J. Org. Chem. 1998, 63, 7674;
53. c) V. A. Nikiforov, V. S. Karavan, S. A. Miltsov, S. I. Selivanov, E. Kolehmainen, E. Wegelius, M. Nissinen, ARKIVOC 2003, VI, 191-200;
54. d) C. Wilgerodt, Ber. Dtsch. Chem. Ges. 1892, 25, 3494-3502.
55. a) M. Crawford, J.W. Rasburn, J. Chem. Soc. 1956, 2155-2160;
56. b) G. Casiraghi, G. Casnati, G. Puglia, G. Sartori, G. Terenghi, J. Chem. Soc. Perkin Trans. 1 1980, 1862-1865.
57. a) K. Srinivasan, P. Michaud, J. K. Kochi, J. Am. Chem. Soc. 1986, 108, 2309-2320;
58. b) P. J. Pospisil, D. H. Carsten, E. N. Jacobsen, Chem. Eur. J. 1996, 2, 974-980;
59. c) J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, C. M. Zepp, J. Org. Chem. 1994, 59, 1939-1942;
60. d) M. Maneiro, M. R. Bermejo, M. I. Fernández, E. Gómez-Fórneas, A. M. González-Noya, A. M. Tyryshkin, New J. Chem. 2003, 27, 727-733.