Palladium-catalyzed α-arylation of sulfoximines

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1351-1354

  Cho, Gae Young ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BROMIDE; PALLADIUM; SULFUR DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; HYDROLYSIS;

EID: 17444374968     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050176b     Document Type: Article

References (42)

1. Hamann, B, C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
2. Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
3. Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. 1997, 36, 1740.
4. For recent examples, see: (a) Muratake, H.; Natsume, M. Angew. Chem., Int. Ed. 2004, 43, 4646. (b) Muratake, H.; Natsume, M.; Nakai, H. Tetrahedron 2004, 60, 11783. (c) Chae, J.; Yun, J.; Buchwald, S. L. Org. Lett. 2004, 6, 4809. (d) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403.
5. For recent examples, see: (a) Muratake, H.; Natsume, M. Angew. Chem., Int. Ed. 2004, 43, 4646. (b) Muratake, H.; Natsume, M.; Nakai, H. Tetrahedron 2004, 60, 11783. (c) Chae, J.; Yun, J.; Buchwald, S. L. Org. Lett. 2004, 6, 4809. (d) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403.
6. For recent examples, see: (a) Muratake, H.; Natsume, M. Angew. Chem., Int. Ed. 2004, 43, 4646. (b) Muratake, H.; Natsume, M.; Nakai, H. Tetrahedron 2004, 60, 11783. (c) Chae, J.; Yun, J.; Buchwald, S. L. Org. Lett. 2004, 6, 4809. (d) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403.
7. For recent examples, see: (a) Muratake, H.; Natsume, M. Angew. Chem., Int. Ed. 2004, 43, 4646. (b) Muratake, H.; Natsume, M.; Nakai, H. Tetrahedron 2004, 60, 11783. (c) Chae, J.; Yun, J.; Buchwald, S. L. Org. Lett. 2004, 6, 4809. (d) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403.
8. For a review on palladium-catalyzed α-arylations of carbonyl compounds and nitriles, see: Culkin, D. A.; Hartwig, J. K. Acc. Chem. Soc. 2003, 36, 234.
9. (a) Kashin, A. N.; Mitin, A. V.; Beleskaya, I. P.; Wife, R. Tetrahedron Lett. 2002, 43, 2539.
10. (b) Mitin, A. V.; Kashin, A. N.; Beleskaya, I. P. J. Organomet. Chem. 2004, 689, 1085.
11. Reviews on sulfoximines: (a) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (b) Pyne, S. G. Sulfur Rep. 1999, 21, 281. (c) Reggelin, M.; Zur, C. Synthesis 2000, 1. (d) Harmata, M. Chemtracts 2003, 16, 660. (e) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482.
12. Reviews on sulfoximines: (a) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (b) Pyne, S. G. Sulfur Rep. 1999, 21, 281. (c) Reggelin, M.; Zur, C. Synthesis 2000, 1. (d) Harmata, M. Chemtracts 2003, 16, 660. (e) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482.
13. Reviews on sulfoximines: (a) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (b) Pyne, S. G. Sulfur Rep. 1999, 21, 281. (c) Reggelin, M.; Zur, C. Synthesis 2000, 1. (d) Harmata, M. Chemtracts 2003, 16, 660. (e) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482.
14. Reviews on sulfoximines: (a) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (b) Pyne, S. G. Sulfur Rep. 1999, 21, 281. (c) Reggelin, M.; Zur, C. Synthesis 2000, 1. (d) Harmata, M. Chemtracts 2003, 16, 660. (e) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482.
15. Reviews on sulfoximines: (a) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341. (b) Pyne, S. G. Sulfur Rep. 1999, 21, 281. (c) Reggelin, M.; Zur, C. Synthesis 2000, 1. (d) Harmata, M. Chemtracts 2003, 16, 660. (e) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482.
16. For recent examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verrucci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
17. For recent examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verrucci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
18. For recent examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verrucci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
19. For recent examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verrucci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
20. For recent examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verrucci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
21. For recent examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321. (c) Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427. (d) Bolm, C.; Verrucci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222. (f) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
22. (a) Mock, W. L.; Tsay, J.-T. J. Am. Chem. Soc. 1989, 111, 4467.
23. (b) Mock, W. L.; Zhang, J. Z. J. Biol. Chem. 1991, 266, 6393.
24. (c) Bolm, C.; Kahmann, J. D.; Moll, G. Tetrahedron Lett. 1997, 38, 1169.
25. (d) Bolm, C.; Moll, G.; Kahmann, J. D. Chem. Eur. J. 2001, 7, 1118.
26. (e) Tye, H.; Skinner, C. L. Helv. Chim. Acta 2002, 85, 3272.
27. (f) Bolm, C.; Müller, D.; Hackenberger, C. P. R. Org. Lett. 2002, 4, 893.
28. (g) Bolm, C.; Müller, D.; Dalhoff, C.; Hackenberger, C. P. R.; Weinhold, E. Bioorg. Med. Chem. Lett. 2003, 13, 3207.
29. (a) Fusco, R.; Tericoni, F. Chem. Ind. (Milan) 1965, 47, 61.
30. (b) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418.
31. (c) Johnson, C. R.; Schroeck, C. W.; Shanklin, J. R. J. Am. Chem. Soc. 1973, 95, 7424.
32. (d) Brandt, J.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 8, 909.
33. In principle, enantiopure aryl benzyl sulfoximines 2 should also be accessible by sterospecific iminations of the corresponding sulfoxides, which can be obtained by methods developed by Naso et al. (see Capozzi, M. A. M.; Cardellicchio, C.; Naso, F.; Rosito, V. J. Org. Chem. 2002, 67, 7289). Then, however, each substrate would have to be prepared individually starting from the corresponding sulfide, which would significantly limit the flexibility and synthetic value of the overall approach towards 2.
34. (a) Bolm, C.; Martin, M.; Gibson, L. Synlett 2002, 832.
35. (b) Bolm, C.; Okamura, H.; Verrucci, M. J. Organomet. Chem. 2003, 687, 444.
36. 2, dppf, and potassium bis(trimethylsilyl)amide (KHMDS) in dioxane at room temperature was rather surprising and will be the subject of further investigations.
37. N-Aroylated sulfoximines are rather stable compounds with a peculiar reactivity pattern (see Bolm, C.; Hackenberger, C. P. R.; Simic, O.; Verrucci, M.; Müller, D.; Bienewald, F. Synthesis 2002, 879). Their treatment with boran-based reducing agents does not lead to the expected N-benzyl derivatives but results in either no conversion or the formation of free NH-sulfoximines. This particular aspect was expected to be benefical in the program described here, since it allowed a selective deprotecting of the α-arylated products under reductive conditions.
38. In this study mostly racemic sulfoximines were used, and generally, the α-arylated products were isolated as a ca. 1:1 mixture of diastereomers (for 8k = 2:1). Based on previous results, we expect that a "chiral switch" should simply lead to idential compounds in enantiomerically pure form.
39. 3 (3 mol %) + BINAP (5 mol %). Use of only 1.1 equiv of PhBr: 79%.
40. Gerisch, M.; Krumper, J. R.; Bergman, R. G.; Tilley, T. D. J. Am. Chem. Soc. 2001, 123, 5818.
41. Rapid decarboxylations have also been observed in reaction sequences involving other α-sulfoximidoyl carboxylates. Since some ammonium salts proved rather stable at ambient temperature, they could be applied in coupling reactions providing sulfoximine-containing pesudo-peptides. For details, see refs 9c and 9d.
42. For a detailed investigation of the nature of the N - C(O)-bond in acylated sulfoximines, see: Hackenberger, C. P. R.; Raabe, G.; Bolm, C. Chem. Eur. J. 2004, 10, 2942.