Aryl(sulfonyl)amino group: A convenient and stable yet activated modification of amino group for its intramolecular displacement

Organic Letters

Volumn 12, Issue 18, 2010, Pages 4137-4139

  Kato, Yuzo ^a   Yen, Dinh Hoang ^a   Fukudome, Yasuhiro ^a   Hata, Takeshi ^a   Urabe, Hirokazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; SULFIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

AMINES; MOLECULAR STRUCTURE; SULFIDES;

EID: 77956589545     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101541p     Document Type: Article

References (49)

1. Textbooks of organic chemistry allot many pages to substitution reactions by amino and related groups, but little is described on the reversed transformation, substitution of amino and related groups. For example, see
2. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 5 th ed.; Springer: New York, 2007; Part A, pp 389 - 472; Part B, pp 215 - 242.
3. McMurry, J. Organic Chemistry, 5 th ed.; Brooks/Cole: Belmont, CA, 2000; pp 976 - 1029.
4. Morrison, R. T.; Boyd, R. N. Organic Chemistry, 6th ed.; Prentice Hall: Upper Saddle River, NJ, 1997; pp 821 - 888.
5. 3 carbon, apart from activated carbon centers such as those at the allylic, benzylic, or acetal position, is usually carried out by its diazotization and quaternarization prior to the substitution. For example, see
6. Smith, M. B.; March, J. Marchs Advanced Organic Chemistry, 6 th ed.; Wiley: Hoboken, NJ, 2007; pp 498 - 500.
7. Solomons, T. W. G.; Fryhle, C. B. Organic Chemistry, 8 th ed.; Wiley: Hoboken, NJ, 2004; pp 963 - 964. For substitution via quaternarization of amines to pyridinium salts, see
8. Katritzky, A. R.; Musumarra, G. Chem. Soc. Rev. 1984, 13, 47-68
9. Katritzky, A. R. Tetrahedron 1980, 36, 679-699 For a broad survey of methods for C-N bond cleavage, see: Harrison, I. T.; Harrison, S.; Hegedus, L. S.; Wade, L. G., Jr.; Smith, M. B. Compendium of Organic Synthetic Methods; Wiley: New York, 1971-1992; Vols. 1-7.
10. Hughes, A. B., Ed. Amino Acids, Peptides and Proteins in Organic Chemistry; Wiley-VCH: Weinheim, 2009; Vols. 1 and 2.
11. Dewick, P. M. Medicinal Natural Products, 3 rd ed.; Wiley: Chichester, 2009.
12. Trauner, D. Chem. Rev. 2008, 108, 1499-1796
13. Gladysz, J. A. Chem. Rev. 2005, 105, 4235-4812
14. Walsh, C. T.; Wright, G. D. Chem. Rev. 2005, 105, 391-774
15. Nugent, T. C., Ed. Chiral Amine Synthesis; Wiley-VCH: Weinheim, 2010.
16. Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63, 2541-2569
17. List, B. Chem. Rev. 2007, 107, 5413-5883
18. Weinreb, S. M.; Orr, R. K. Synthesis 2005, 1205-1227
19. For sulfonylation of amines and anilines, see
20. Wuts, P. G. M.; Greene, T. W. Greenes Protective Groups in Organic Synthesis, 4 th ed.; Wiley: Hoboken, NJ, 2007; pp 851 - 868.
21. Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: Stuttgart, 1994; pp 212 - 216.
22. For o -nitrophenylation of amines or sulfonamides, see
23. Kulagowski, J. J.; Rees, C. W. Synthesis 1980, 215
24. Burke, P. O.; Spillane, W. J. Synthesis 1985, 935-937
25. Newington, I.; Perez-Arlandis, J. M.; Welton, T. Org. Lett. 2007, 9, 5247-5250 An actual procedure adopted in our laboratory is simpler; see the Supporting Information
26. For reviews on recent progress in transition-metal-catalyzed N -arylation of both amines and sulfonamides, see
27. Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075
28. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449
29. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428-2439
30. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2008, 47, 3096-3099
31. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450-1460
32. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534-1544 For arylation of sulfonamides, see: Deng, W.; Liu, L.; Zhang, C.; Liu, M.; Guo, Q.-X. Tetrahedron Lett. 2005, 46, 7295-7298
33. Steinhuebel, D.; Palucki, M.; Askin, D.; Dolling, U. Tetrahedron Lett. 2004, 45, 3305-3307
34. Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101-1104
35. Some fundamental results of cyclization are shown in the Supporting Information.
36. Although disulfonylamine (sulfonimide) has been known to work as a leaving group since the late 1960s, its synthetic utility has not been well explored. To the best of our knowledge, intramolecular cyclization with this group has not been reported. This most likely comes from the fact that the requisite disulfonylamine is difficult to prepare in the presence of an (incipient) nucleophile, as this functional group is rather labile and behaves, at the same time, as a sulfonylating agent. For selected initial studies, see
37. DeChristopher, P. J.; Adamek, J. P.; Lyon, G. D.; Galante, J. J.; Haffner, H. E.; Boggio, R. J.; Baumgarten, R. J. J. Am. Chem. Soc. 1969, 91, 2384-2385
38. Muöller, P.; Phuong, N. T. M. Tetrahedron Lett. 1978, 4727-4730 and references cited therein. For recent reports, see
39. Wang, X.; Mei, T.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 7520-7521
40. Toulgoat, F.; Langlois, B. R.; Médebielle, M.; Sanchez, J.-Y. J. Org. Chem. 2008, 73, 5613-5616
41. Said, S. A.; Fiksdahl, A. Tetrahedron: Asymmetry 2001, 12, 893-896
42. Lescop, C.; Mévellec, L.; Huet, F. J. Org. Chem. 2001, 66, 4187-4193 For sulfonylation with disulfonylamines, see: Hendrickson, J. B.; Sternbach, D. D.; Bair, K. W. Acc. Chem. Res. 1977, 10, 306-312
43. Zeller, W. E. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, 1995; Vol. 6, pp 4096 - 4097.
44. Kotsuki, H.; Kadota, I.; Ochi, M. J. Org. Chem. 1990, 55, 4417-4422 and references cited therein
45. Wuts, P. G. M.; Greene, T. W. Greenes Protective Groups in Organic Synthesis, 4 th ed.; Wiley: Hoboken, NJ, 2007; pp 813 - 814.
46. For chemoselective N -arylation of amino alcohols, see
47. Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703-3706
48. Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490-3491
49. Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402-3404