Palladium-catalyzed coupling reaction of diaryl dichalcogenide with aryl bromide leading to the synthesis of unsymmetrical aryl chalcogenide

Synlett

Volumn , Issue 13, 2006, Pages 2145-2147

  Fukuzawa, Shin Ichi ^a   Tanihara, Daisuke ^a   Kikuchi, Satoshi ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

Catalysis; Cross coupling; Palladium; Selenium; Sulfur

Indexed keywords

BROMIDE; PALLADIUM; SELENIDE; SULFIDE; ZINC;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; SYNTHESIS;

EID: 33748280948     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949607     Document Type: Article

References (37)

1. (a) Kondo, T.; Mitsudo, T.-A. Chem. Rev. 2000, 100, 3205.
2. (b) Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400.
3. (a) Solladie, G. Synthesis of Sulfides, Sulfoxides and Sulfones, Vol. 6; Pergamon Press: Oxford, 1991, 133-170.
4. (b) Baird, C. P.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 1998, 1973.
5. (c) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 1999, 641.
6. (d) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 835.
7. (e) Procter, D. J. J. Chem. Soc., Perkin Trans, 1 2001, 335.
8. For examples of the copper-catalyzed coupling reaction, see: (a) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
9. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
10. (c) Wu, Y.-J.; He, H. Synlett 2003, 1789.
11. (d) Deng, W.; Zou, Y.; Wang, Y.-F.; Liu, L.; Guo, Q.-X. Synlett 2004, 1254.
12. For an example of the nickel-catalyzed coupling reaction, see: Takagi, K. Chem. Lett. 1987, 2221.
13. For examples of the palladium-catalyzed coupling reaction, see: (a) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13.
14. (b) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385.
15. (c) Zheng, N.; McWilliams, J. C.; Fleitz, F. J.; Armstrong, J. D. III; Volante, R. P. J. Org. Chem. 1998, 63, 9606.
16. (d) Schopfer, U.; Schlapbach, A. Tetrahedron 2001, 57, 3069.
17. (e) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677.
18. (f) Li, G. Y. Angew. Chem. Int. Ed. 2001, 40, 1513.
19. (g) Li, G. Y. J. Org. Chem. 2002, 67, 3643.
20. (h) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
21. (i) Fernãndez-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
22. Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019.
23. (a) Taniguchi, N. J. Org. Chem. 2004, 69, 6904.
24. (b) Taniguchi, N.; Onami, T. Synlett 2003, 829.
25. (c) Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
26. (d) Millois, C.; Diaz, P. Org. Lett. 2000, 2, 1705.
27. For examples, see: (a) Organoselenium Chemistry: A Practical Approach in Chemistry; Back, T. G., Ed.; Oxford Press: Oxford, 1999.
28. (b) Organoselenium Chemistry, In Topics in Current Chemistry, Vol. 208; Wirth, T., Ed.; Springer: Berlin, 2000.
29. Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193.
30. The copper-catalyzed reaction of bromobenzene with diphenyl disulfide produced only a 34% yield of diphenyl sulfide. See ref. 7a.
31. 4). A GC-MS analysis of the ethereal solution showed the presence of the corresponding unsymmetrical sulfide, and the yield was determined using biphenyl as an internal standard. The aryl sulfide was isolated by PTLC and fully characterized.
32. The reaction with p-iodonitrobenzene proceeded to give the corresponding aryl sulfide in 82% yield.
33. Magnesium was used instead of zinc for the reaction with 2-bromothiophene.
34. Adapa et al. reported the stoichiometric coupling reaction between aryl bromides with diphenyl diselenides using CsOH. See: Varala, R.; Ramu, E.; Adapa, S. R. Bull. Chem. Soc. Jpn. 2006, 79, 140.
35. The Se-Se bond in diphenyl diselenide was reductively cleaved by low valent indium and the generated selenoindium species react with alkyl halides (not aryl) to give alkyl aryl selenides. See: (a) Ranu, B. C.; Mandal, T.; Samanta, S. Org. Lett. 2003, 5, 1439.
36. (b) Ranu, B. C.; Mandai, T. J. Org. Chem. 2004, 69, 5793.
37. The ruthenium-catalyzed coupling reaction of diphenyl diselenide with alkyl halides in the presence of zinc has been reported, where cleavage of the Se-Se bond takes place. See: Zhao, X.; Yu, Z.; Yan, S.; Wu, S.; Liu, R.; He, W.; Wang, L. J. Org. Chem. 2005, 70, 7338.