Dioxygen-Coupled Oxidative Amination of Styrene

Journal of the American Chemical Society

Volumn 125, Issue 43, 2003, Pages 12996-12997

  Timokhin, Vitaliy I ^a   Anastasi, Natia R ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; OXAZOLIDINONE DERIVATIVE; OXYGEN; STYRENE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE;

ALKENES; AMINATION; AMINES; OXIDATION-REDUCTION; OXYGEN; STYRENE;

EID: 0142214634     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0362149     Document Type: Article

References (32)

1. For recent reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
2. (b) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 113-151.
3. (c) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamomoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618.
4. (d) Brunet, J. J.; Neibecker, D. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: New York, 2001; pp 91-141.
5. For intramolecular aerobic oxidative amination methods, see: (a) van Benthem, R. A. T. M.; Hiemstra, H.; Longarela, G. R.; Speckamp, W. N. Tetrahedron Lett. 1994, 35, 9281-9284.
6. (b) Rönn, M.; Bäckvall, J.-E.; Andersson, P. G. Tetrahedron Lett. 1995, 36, 7749-7752.
7. (c) Larock, R. C., Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584-3585.
8. (d) Fix, S. R.; Brice, J. L.; Stahl, S. S. Angew. Chem., Int. Ed. 2002, 41, 164-166.
9. (a) Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S.-I. Tetrahedron Lett. 1992, 33, 6643-6646.
10. (b) Ragaini, F.; Longo, T.; Cenini, S. J. Mol. Catal. A-Chem. 1996, 110, L171-L175.
11. Recent examples of rhodium-catalyzed oxidative amination have been reported in which styrene serves a dual role as a substrate and a sacrificial oxidant. For leading references, see: (a) Brunet, J. J.; Neibecker, D.; Philippot, K. Tetrahedron Lett. 1993, 34, 3877-3880.
12. (b) Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Herwig, J.; Muller, T. E.; Thiel, O. R. Chem.-Eur. J. 1999, 5, 1306-1319.
13. Protonation of palladium(0) could promote the novel palladium(II)-hydride-mediated hydroamination reaction described recently by Hartwig and coworkers. (a) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547.
14. (b) Nettekoven, U.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1166-1167.
15. Catalyst/additive loadings and product yields are reported relative to oxazolidinone, which is usually the limiting reagent.
16. For numerous examples of triethylamine used as a base in palladium-catalyzed cross-coupling reactions, see: Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
17. Direct amination of the benzylic C-H bond cannot be excluded, but we consider this less likely. For recent characterization of palladium migration after nucleophilic attack on a coordinated olefin, see: Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 2056-2057.
18. Seligson, A. L.; Trogler, W. C. J. Am. Chem. Soc. 1991, 113, 2520-2527.
19. Previous studies reveal that steric properties of secondary amine and olefin substrates influence the regiochemistry of palladium-mediated olefin amination. See ref 1a.
20. 3 can be successfully replaced by other donor ligands, such as the N-heterocyclic carbene, 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene) (IPr).
21. Hegedus, L. S.; Åkermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 106, 7122-7126.
22. Base effects have also been observed in palladium-catalyzed aerobic alcohol oxidation, see: (a) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202-8203.
23. (b) Schultz, M. J.; Park, C. C.; Sigman, M. S. Chem. Commun. 2002, 3034-3035.
24. (c) Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835-837.
25. (d) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179-4181.
26. (a) Cowan, R. L.; Trogler, W. C. Organometallics 1987, 6, 2451-2453.
27. (b) Seul, J. M.; Park, S. J. Chem. Soc., Dalton Trans. 2002, 1153-1158.
28. Anastasi, N. R., Stahl, S. S., unpublished results.
29. For leading references on direct dioxygen-coupled palladium oxidation catalysis, see the following and references therein: (a) refs 2 and 13.
30. (b) Sheldon, R. A.; Arends, I.; Ten Brink, G. J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774-781.
31. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750-6755.
32. (d) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188-7189.