Synthesis of sulfones by iron-catalyzed decomposition of sulfonylhydrazones

European Journal of Organic Chemistry

Volumn , Issue 8, 2011, Pages 1520-1526

  Barluenga, José ^a   Tomás Gamasa, María ^a   Aznar, Fernando ^a   Valdés, Carlos ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Carbenes; Cross coupling; Diazo compounds; Hydrazones; Iron; Sulfur

Indexed keywords

EID: 79952129476     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001492     Document Type: Article

References (55)

1. P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998, p. 30.
2. R. A. Sheldon, I. Arends, U. Hanefeld, Green Chemistry and Catalysis, Wiley-VCH, Weinheim, 2007.
3. P. Anastas, N. Eghbali, Chem. Soc. Rev. 2010, 39, 301-312.
4. For a review on the applications of tosylhydrazones in metal-catalyzed processes prior to our work, see:, J. R. Fulton, V. K. Aggarwal, J. de Vicente, Eur. J. Org. Chem. 2005, 8, 1479-1492.
5. J. Barluenga, P. Moriel, C. Valdés, F. Aznar, Angew. Chem. 2007, 119, 5683
6. Angew. Chem. Int. Ed. 2007, 46, 5587-5590.
7. J. Barluenga, M. Tomás-Gamasa, P. Moriel, F. Aznar, C. Valdés, Chem. Eur. J. 2008, 14, 4792-4795.
8. J. Barluenga, M. Escribano, P. Moriel, F. Aznar, C. Valdés, Chem. Eur. J. 2009, 15, 13291-13294.
9. J. Barluenga, M. Escribano, F. Aznar, C. Valdés, Angew. Chem. Int. Ed. 2010, 49, 6856-6859.
10. J. Barluenga, M. Tomás-Gamasa, F. Aznar, C. Valdés, Nature Chem. 2009, 1, 433-499.
11. J. Barluenga, M. Tomás-Gamasa, F. Aznar, C. Valdés, Angew. Chem. Int. Ed. 2010, 49, 4993-4496.
12. X. Xiao, J. Ma, Y. Yang, Y. Zhang, J. Wang, Org. Lett. 2009, 11, 4732-4735.
13. X. Zhao, J. Jing, K. Lu, Y. Zhang, J. Wang, Chem. Commun. 2010, 46, 1724-1726.
14. Z. Zhang, Y. Liu, M. Gong, X. Zhao, Y. Zhang, J. Wang, Angew. Chem. 2010, 122, 1157
15. Angew. Chem. Int. Ed. 2010, 49, 1139-1142.
16. B. Tréguier, A. Hamze, O. Provot, J.-D. Brion, M. Alami, Tetrahedron Lett. 2009, 50, 6549-6552.
17. For some reviews detailing synthetic applications of sulfones, see
18. S. Patai, Z. Rappoport, C. Stifling (Eds.), The Chemistry of Sulfones and Sulfoxides, Wiley, Chichester, 1988.
19. N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993.
20. C. Nájera, M. Yus, Tetrahedron 1999, 55, 10547-10658.
21. P. R. Blakemore, J. Chem. Soc. Perkin Trans. 1 2002, 2563-2585.
22. For some recent examples, see
23. A.-M. Faucher, P. W. White, C. Brochu, C. Grand-Maëtre, J. Rancourt, G. Fazal, J. Med. Chem. 2004, 47, 18-21.
24. M. Teall, P. Oakley, T. Harrison, D. Shaw, E. Kay, J. Elliott, U. Gerhard, J. L. Castro, M. Shearman, R. G. Ball, N. N. Tsou, Bioorg. Med. Chem. Lett. 2005, 15, 2685-2868.
25. A. R. Usera, P. Dolan, T. W. Kensler, G. H. Posner, Bioorg. Med. Chem. 2009, 17, 5627-5631.
26. R. C. Bernotas, R. R. Singhaus, D. H. Kaufman, J. M. Travins, J. W. Ullrich, R. Unwalla, E. Quinet, M. Evans, P. Nambi, A. Olland, B. Kauppi, A. Wilhelmsson, A. Goos-Nilsson, J. Wrobel, Bioorg. Med. Chem. Lett. 2010, 20, 209-212.
27. T. K. Sasikumar, L. Qiang, D. A. Burnett, D. Cole, R. Xu, H. Li, W. J. Greenlee, J. Clader, L. Zhang, L. Hyde, Bioorg. Med. Chem. Lett. 2010, 20, 3632-3635.
28. J.-L. Zhang, P. W. H. Chan, C.-M. Che, Tetrahedron Lett. 2003, 44, 8733.
29. X.-W. Feng, J. Wang, J. Zhang, J. Yang, N. Wang, X.-Q. Yu, Org. Lett. 2010, 12, 4408-4411.
30. For recent reviews on iron-catalyzed cross-coupling reactions, see
31. B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1511.
32. W. M. Czaplik, M. Mayer, A. J. von Wangelin, ChemSusChem 2009, 2, 396-417.
33. F. A. Cotton, G. Wilkinson, Inorganic Chemistry, 4th ed., Verlag Chemie, Weinheim, 1982, p. 767.
34. W. R. Bamford, T. S. Stevens, J. Chem. Soc. 1952, 4735-4740.
35. B. Bogdanović, M. Schwickardi, Angew. Chem. 2000, 112, 4788
36. Angew. Chem. Int. Ed. 2000, 39, 4610-4612.
37. L. E. Aleandri, B. Bodganović, P. Bons, C. Dürr, A. Gaidies, T. Hartwig, S. C. Huckett, M. Lagarden, U. Wilczok, R. A. Brand, Chem. Mater. 1995, 7, 1153-1170.
38. V. K. Aggarwal, J. R. Fulton, C. G. Sheldon, J. de Vicente, J. Am. Chem. Soc. 2003, 125, 6034-6035.
39. H.-S. Jeon, J. E. Yeo, Y. C. Jeong, S. Koo, Synthesis 2004, 17, 2813-2820.
40. S. Chandrasekhar, V. Jagadeshwar, B. Saritha, C. Narsihmulu, J. Org. Chem. 2005, 70, 6506-6507.
41. M. Aoki, K. Kawashima, H. Fujihara, I. Shimizu, Chem. Lett. 2007, 36, 654-655.
42. N. Charrier, S. Z. Zard, Angew. Chem. 2008, 120, 9585
43. Angew. Chem. Int. Ed. 2008, 47, 9443-9446.
44. For examples of the application of sulfinate anions as nucleophiles in the synthesis of sulfones, see
45. B. M. Trost, M. L. Crawley, C. B. Lee, J. Am. Chem. Soc. 2000, 122, 6120-6121.
46. Y. Ju, D. Kumar, R. S. Varma, J. Org. Chem. 2006, 71, 6697-6700.
47. M. Ueda, J. F. Hartwig, Org. Lett. 2010, 12, 92-94 and references cited therein.
48. V. K. Aggarwal, E. Alonso, I. Bae, G. Hynd, K. M. Lydon, M. J. Palmer, M. Patel, M. Porcelloni, J. Richardson, R. A. Stenson, J. R. Studley, J.-L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2003, 125, 10926-10940.
49. T. Niwa, H. Yorimitsu, K. Oshima, Tetrahedron 2009, 65, 1971-1976.
50. A. A. El-Bardan, E. A. Hamed, E. F. Saad, J. Chem. Eng. Data 1989, 34, 133-1334.
51. R. Kuwano, Y. Rondo, T. Shirahawa, Org. Lett. 2005, 7, 2973-2975.
52. V. I. Timokhin, S. Gastaldi, M. P. Bertrand, C. Chatgilialoglu, J. Org. Chem. 2003, 68, 3532-3537.
53. F.-X. Felpin, Y. Landais, J. Org. Chem. 2005, 70, 6441-6446.
54. K. Saito, H. Ishihara, Heterocycles 1986, 24, 1291-1294.
55. H. L. Holland, F. M. Brown, B. G. Larsen, Tetrahedron: Asymmetry 1995, 6, 1561-1567.