Oxidative coupling of dichalcogenides with sodium sulfinates via copper-catalyzed cleavage of s-s and se-se bonds

Journal of Organic Chemistry

Volumn 80, Issue 3, 2015, Pages 1764-1770

  Taniguchi, Nobukazu ^a  

^a FUKUSHIMA MEDICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; SODIUM;

COPPER CATALYZED; DICHALCOGENIDES; OXIDATIVE COUPLINGS; SULFINATES; SULFONYLATION;

CATALYSIS;

CHEMICAL COMPOUND; COPPER; DICHALCOGENIDE DERIVATIVE; OXYGEN; SODIUM SULFINATE DERIVATIVE; SULFONE; SULFUR; UNCLASSIFIED DRUG; CHALCOGEN; DISULFIDE; SELENIUM; SULFINIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; OXIDATIVE COUPLING; REACTION ANALYSIS; SULFONYLATION; CHEMISTRY;

CATALYSIS; CHALCOGENS; COPPER; DISULFIDES; OXIDATIVE COUPLING; SELENIUM; SULFINIC ACIDS;

EID: 84922735155     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5026805     Document Type: Article

References (52)

1. Metzner, P.; Thuillier, A. Sulfur Reagents in Organic Synthesis; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: San Diego, CA, 1994.
2. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press Ltd.: New York, 1991; Vol. 6.
3. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Baldwin, J. E., Ed.; Organic Chemistry Series 4; Pergamon Press Ltd.: Oxford, 1986.
4. Organoselenium Chemistry; Wirth, T., Ed.; Springer-Verlag; Heidelberg, 2000.
5. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449
6. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205-3220
7. Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596-1636
8. Partyka, D. V. Chem. Rev. 2011, 111, 1529-1595
9. Field, L.; Parsons, T. F. J. Org. Chem. 1965, 30, 657-659
10. Chau, M. M.; Kice, J. L. J. Am. Chem. Soc. 1976, 98, 7711-7716
11. Cai, M.-T.; Lv, G.-S.; Chen, J.-X.; Gao, W.-X.; Ding, J.-C.; Wu, H.-Y. Chem. Lett. 2010, 39, 368-369
12. Iranpoor, N.; Firouzabadi, H.; Pourali, A.-R. Synlett 2004, 347-349
13. Sobhani, S.; Aryanejad, S.; Maleki, M. F. Synlett 2011, 319-322
14. Emmett, E. J.; Hayter, B. R.; Willis, M. C. Angew. Chem., Int. Ed. 2013, 52, 12679-12683
15. Deeming, A. S.; Russell, C. J.; Hennessy, A. J.; Willis, M. C. Org. Lett. 2014, 16, 150-153
16. Sugata, K.; Song, L.; Nakamura, M.; Ueki, S.; Fajer, P. G.; Arata, T. J. Mol. Biol. 2009, 386, 626-636
17. Tiebel, B.; Radzwill, N.; Aung-Hilbrich, L. M.; Helbl, V.; Steinhoff, H.-J.; Hillen, W. J. Mol. Biol. 1999, 290, 229-240
18. Gancarz, A. R.; Kice, L. J. J. Org. Chem. 1981, 46, 4899-4906
19. Oxidative reaction sulfenylation: Allen, S. E.; Walvoord, R. R.; Padilla-Salinas, R.; Kozlowski, M. C. Chem. Rev. 2013, 113, 6234-6458
20. Block, E.; OConnor, J. J. Am. Chem. Soc. 1974, 96, 3921-3929
21. Iranpoor, N.; Firouzabadi, H.; Poural, A.-R. Synlett 2004, 347-349
22. Bahrami, K.; Khodaei, M. M.; Khaledian, D. Tetrahedron Lett. 2012, 53, 354-358
23. Sobhani, S.; Aryanejad, S.; Maleki, M. F. Synlett 2011, 319-322
24. Bently, M. D.; Douglass, I. B.; Lacadie, J. A. J. Org. Chem. 1972, 37, 333-334
25. Oae, S.; Takata, T.; Kim, Y. H. Bull. Chem. Soc. Jpn. 1982, 55, 2484-2494
26. Oae, S.; Tanaka, T.; Kim, Y. H. Tetrahedron 1981, 37, 37-44
27. Fujiki, K.; Tanifuji, N.; Sasaki, Y.; Yokoyama, T. Syntheses 2002, 343-348
28. Alcaraz, M.-L.; Atkinson, S.; Cornwall, P.; Foster, A. C.; Gill, D. M.; Humphries, L. A.; Keegan, P. S.; Kemp, R.; Merifield, E.; Nixon, R. A.; Noble, A. J.; OBeirne, D.; Patel, Z. M.; Perkins, J.; Rowan, P.; Sadler, P.; Singleton, J. T.; Tornos, J.; Watts, A. J.; Woodland, I. A. Org. Process Res. Dev. 2005, 9, 555-569
29. Liang, G.; Liu, M.; Chen, J.; Ding, J.; Gao, W.; Wu, H. Chin. J. Chem. 2012, 30, 1611-1616
30. Chen, D.-W.; Chen, Z.-C. Tetrahedron Lett. 1994, 35, 7637-7638
31. Liang, G.; Chen, J.; Li, W.; Chen, J.; Wu, H. Tetrahedron Lett. 2012, 53, 6768-6770
32. Comprehensive Organic Chemistry; Neville, J. D., Ed.; Pergamon Press Ltd.: Oxford, 1979; Vol. 3.
33. Bewick, A.; Mellor, J. M.; Milano, D.; Owton, W. M. J. Chem. Soc., Perkin Trans. 1 1985, 1045-1048
34. Bach, R. D.; Rajan, S. J.; Vardhan, H. B.; Lang, T. J.; Albrecht, N. G. J. Am. Chem. Soc. 1981, 103, 7727-7734
35. Ichimura, A.; Nosco, D. L.; Deutsch, E. J. Am. Chem. Soc. 1983, 105, 844-850
36. Suzuki, H.; Abe, H.; Osuka, A. Chem. Lett. 1980, 1363-1364
37. Suzuki, H.; Abe, H.; Osuka, A. Chem. Lett. 1981, 151-152
38. Bowman, W. R.; Heaney, H.; Smith, P. H. G. Tetrahedron Lett. 1984, 25, 5821-5824
39. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517-3520
40. Gujadhur, R. K.; Venkataruman, D. Tetrahedron Lett. 2003, 44, 81-84
41. Taniguchi, N. Eur. J. Org. Chem. 2014, 5691-5694
42. Kadooka, M. M.; Warner, L. G.; Seff, K. J. Am. Chem. Soc. 1976, 98, 7569-7578
43. Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915-920
44. Taniguchi, N. J. Org. Chem. 2006, 71, 7874-7876
45. Taniguchi, N. J. Org. Chem. 2007, 72, 1241-1245
46. Taniguchi, N. Eur. J. Org. Chem. 2010, 2670-2673
47. Many examples are described: Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Ed.; Wiley-VCH; Weinheim, 2004.
48. Organic Syntheses; Baumgarten, H. E., Ed.; John Wiley & Sons, New York, 1973; Collect. Vol. 5, pp 107-110.
49. Odani, A.; Maruyama, T.; Yamaguchi, O.; Fujiwara, T.; Tomita, K.-i. J. Chem. Soc., Chem. Commun. 1982, 646-647
50. Higashi, L. S.; Lundeen, M.; Milti, E.; Seff, K. Inorg. Chem. 1977, 16, 310-313
51. Kochi, J. K.; Organometallic Mechanisms and Catalysis; Academic Press: San Diego, CA, 1978.
52. Weider, J. P.; Block, S. S. J. Med. Chem. 1967, 10, 1167-1170