Copper-catalyzed synthesis of thiosulfonates by oxidative coupling of thiols with sodium sulfinates

European Journal of Organic Chemistry

Volumn 2014, Issue 26, 2014, Pages 5691-5694

  Taniguchi, Nobukazu ^a  

^a FUKUSHIMA MEDICAL UNIVERSITY   (Japan)

Author keywords

Copper; Oxidative coupling; Sulfinates; Sulfur; Synthetic methods; Thiols

Indexed keywords

EID: 84908343464     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201402847     Document Type: Article

References (36)

1. a) B. M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis, Pergamon, New York, 1991, vol. 4;
2. b) F.A. Davis, J. Org. Chem. 2006, 71, 8993-9003.
3. a) A. Krief, Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, New York, 1995, vol. 11, chapter 13;
4. b) A. de Meijere, F. Diederich (Eds.), Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 2004;
5. c) S. V. Ley, A. W. Thomas, Angew. Chem. Int. Ed. 2003, 42, 5400-5449;
6. Angew. Chem. 2003, 115, 5558-5607;
7. d) T. Kondo, T. Mitsudo, Chem. Rev. 2000, 100, 3205-3220;
8. e) I. P. Beletskaya, V. P. Ananikov, Chem. Rev. 2011, 111, 1596-1636;
9. f) D. V. Partyka, Chem. Rev. 2011, 111, 1529-1595.
10. P. Metzner, A. Thuillier, Sulfur Reagents in: Organic Synthesis (Eds.: A. R. Katritzky, O. Meth-Cohn, C. W. Rees), Academic, San Diego, USA, 1994.
11. a) K. Sugata, L. Song, M. Nakamura, S. Ueki, P. G. Fajer, T. Arata, J. Mol. Biol. 2009, 386, 626-636;
12. b) B. Tiebel, N. Radzwill, L. M. Aung-Hilbrich, V. Helbl, H.-J. Steinhoff, W. Hillen, J. Mol. Biol. 1999, 290, 229-240.
13. a) L. Field, T. F. Parsons, J. Org. Chem. 1965, 30, 657-659;
14. b) M. M. Chau, J. L. Kice, J. Am. Chem. Soc. 1976, 98, 7711-7716;
15. c) M.-T. Cai, G.-S. Lv, J.-X. Chen, W.-X. Gao, J.-C. Ding, H.-Y. Wu, Chem. Lett. 2010, 39, 368-369;
16. d) N. Iranpoor, H. Firouzabadi, A.-R. Pourali, Synlett 2004, 347-349;
17. e) M. Kiriyama, S. Narito, Y. Ishizuka, H. Hanai, T. Noguchi, Tetrahedron Lett. 2011, 52, 3086-3089;
18. f) S. Sobhani, S. Aryanejad, M. F. Maleki, Synlett 2011, 319-322;
19. g) K. Bahrami, M. M. Khodaei, D. Khaledian, Tetrahedron Lett. 2012, 53, 354-358.
20. a) S. Oae, T. Takata, Y. H. Kim, Bull. Chem. Soc. Jpn. 1982, 55, 2484-2494;
21. b) S. Oae, T. Tanaka, Y. H. Kim, Tetrahedron 1981, 37, 37-44;
22. c) K. Fujiki, N. Tanifuji, Y. Sasaki, T. Yokoyama, Synthesis 2002, 343-348;
23. d) M.-L. Alcaraz, S. Atkinson, P. Cornwall, A. C. Foster, D. M. Gill, L. A. Humphries, P. S. Keegan, R. Kemp, E. Merifield, R. A. Nixon, A. J. Noble, D. O'Beirne, Z. M. Patel, J. Perkins, P. Rowan, P. Sadler, J. T. Singleton, J. Tornos, A. J. Watts, I. A. Woodland, Org. Process Res. Dev. 2005, 9, 555-569.
24. a) E. Block, J. O'Connor, J. Am. Chem. Soc. 1974, 96, 3921-3929;
25. b) M. D. Bently, I. B. Douglass, J. A. Lacadie, J. Org. Chem. 1972, 37, 333-334.
26. a) G. Liang, J. Chen, W. Li, J. Chen, H. Wu, Tetrahedron Lett. 2012, 53, 6768-6770;
27. b) G. Liang, M. Liu, J. Chen, J. Ding, W. Gao, H. Wu, Chin. J. Chem. 2012, 30, 1611-1616.
28. a) A. Bewick, J. M. Mellor, D. Milano, W. M. Owton, J. Chem. Soc. Perkin Trans. 1 1985, 1045-1048;
29. b) R. D. Bach, S. J. Rajan, H. B. Vardhan, T. J. Lang, N. G. Albrecht, J. Am. Chem. Soc. 1981, 103, 7727-7734;
30. c) A. Ichimura, D. L. Nosco, E. Deutsch, J. Am. Chem. Soc. 1983, 105, 844-850.
31. S. E. Allen, R. R. Walvoord, R. Padilla-Salinas, M. C. Kozlowski, Chem. Rev. 2013, 113, 6234-6458.
32. a) N. Taniguchi, J. Org. Chem. 2007, 72, 1241-1245;
33. b) N. Taniguchi, Eur. J. Org. Chem. 2010, 2670-2673;
34. c) N. Taniguchi, Tetrahedron 2014, 70, 1984-1990;
35. d) M. M. Kadooka, L. G. Warner, K. Seff, J. Am. Chem. Soc. 1976, 98, 7569-7578.
36. Organic Syntheses, Coll. Vol. V, Wiley, New York, 1973, p. 107-110.