Aerobic oxidative amination of unactivated alkenes catalyzed by palladium

Journal of the American Chemical Society

Volumn 127, Issue 9, 2005, Pages 2868-2869

  Brice, Jodie L ^a   Harang, Jenna E ^a   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 DERIVATIVE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL BOND; OXIDATION; X RAY CRYSTALLOGRAPHY;

AEROBIOSIS; ALKENES; AMINATION; AMINES; CATALYSIS; IMINES; NORBORNANES; OXIDATION-REDUCTION; PALLADIUM;

EID: 14844317635     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0433020     Document Type: Article

References (32)

1. For recent reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703. (b) Brunet, J. J.; Neibecker, D. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: New York, 2001; pp 91-141. (c) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594. (d) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
2. For recent reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703. (b) Brunet, J. J.; Neibecker, D. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: New York, 2001; pp 91-141. (c) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594. (d) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
3. For recent reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703. (b) Brunet, J. J.; Neibecker, D. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: New York, 2001; pp 91-141. (c) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594. (d) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
4. For recent reviews, see: (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703. (b) Brunet, J. J.; Neibecker, D. In Catalytic Heterofunctionalization; Togni, A., Grützmacher, H., Eds.; Wiley-VCH: New York, 2001; pp 91-141. (c) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579-1594. (d) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
5. For additional leading references, see: (a) Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 12584-12605. (b) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547. (c) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14286-14287. (d) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2702-2703.
6. For additional leading references, see: (a) Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 12584-12605. (b) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547. (c) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14286-14287. (d) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2702-2703.
7. For additional leading references, see: (a) Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 12584-12605. (b) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547. (c) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14286-14287. (d) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2702-2703.
8. For additional leading references, see: (a) Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 12584-12605. (b) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547. (c) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14286-14287. (d) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2702-2703.
9. Alkyl olefin reactivity has generally been limited to reactions with ethylene and propylene under elevated pressure: (a) Coulson, D. R. Tetrahedron Lett. 1971, 12, 429-430. (b) Brunei, J.-J.; Cadena, M.; Chu, N. C.; Diallo, O.; Jacob, K.; Mothes. E. Organometallics 2004, 23, 1264-1268. (c) Wang, X.; Widenhoefer, R. A. Organometallics 2004, 23, 1649-1651.
10. Alkyl olefin reactivity has generally been limited to reactions with ethylene and propylene under elevated pressure: (a) Coulson, D. R. Tetrahedron Lett. 1971, 12, 429-430. (b) Brunei, J.-J.; Cadena, M.; Chu, N. C.; Diallo, O.; Jacob, K.; Mothes. E. Organometallics 2004, 23, 1264-1268. (c) Wang, X.; Widenhoefer, R. A. Organometallics 2004, 23, 1649-1651.
11. Alkyl olefin reactivity has generally been limited to reactions with ethylene and propylene under elevated pressure: (a) Coulson, D. R. Tetrahedron Lett. 1971, 12, 429-430. (b) Brunei, J.-J.; Cadena, M.; Chu, N. C.; Diallo, O.; Jacob, K.; Mothes. E. Organometallics 2004, 23, 1264-1268. (c) Wang, X.; Widenhoefer, R. A. Organometallics 2004, 23, 1649-1651.
12. Jira, R. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: New York, 2002; Vol. 1, pp 386-405.
13. Hegedus, L. S. Tetrahedron 1984, 40, 2415-2434.
14. (a) Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S.-I. Tetrahedron Lett. 1992, 33, 6643-6646.
15. (b) Ragaini, F.; Longo, T.; Cenini, S. J. Mol. Catal. A: Chem. 1996, 770, L171-L175.
16. Timokhin, V. I.; Anastasi, N. R.; Stahl. S. S. J. Am. Chem. Soc. 2003, 125, 12996-12997.
17. A complementary catalytic strategy for the oxidative amination of alkenes features catalytic transfer of an electrophilic nitrene (or nitrenoid) to the alkene and commonly employs a hypervalent iodine-based oxidant. For leading references, see: (a) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 113-151. (b) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamomoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (c) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672-13673.
18. A complementary catalytic strategy for the oxidative amination of alkenes features catalytic transfer of an electrophilic nitrene (or nitrenoid) to the alkene and commonly employs a hypervalent iodine-based oxidant. For leading references, see: (a) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 113-151. (b) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamomoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (c) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672-13673.
19. A complementary catalytic strategy for the oxidative amination of alkenes features catalytic transfer of an electrophilic nitrene (or nitrenoid) to the alkene and commonly employs a hypervalent iodine-based oxidant. For leading references, see: (a) Müller, P. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press Inc.: Greenwich, CT, 1997; Vol. 2, pp 113-151. (b) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamomoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 607-618. (c) Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672-13673.
20. (a) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744.
21. (b) Dorta, R.; Egli, P.; Zürcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857-10858.
22. (c) Brunet, J.-J.; Chu, N. C.; Diallo, O.; Mothes, E. J. Mol. Catal. A: Chem. 2003, 198, 107-110.
23. (d) Ackermann, L.; Kaspar, L. T.; Gschrei, C. J. Org. Lett. 2004, 6, 2515-2518.
24. (e) Anderson, L. L.; Arnold, J.; Bergman, R. G. Org. Lett. 2004, 6, 2519-2522.
25. 2O that produces a tetrahydrofuran structure: Koo, K.; Hillhouse, G. L. Organometallics 1998, 17, 2924-2925.
26. Ney, J. E.; Wolfe, J. P. Angew. Chem., Int. Ed. 2004, 43, 3605-3608 and references therein.
27. Examples of trans-aminopalladation are well documented. For leading references, see: (a) Bäckvall, J.-E. Acc. Chem. Res. 1983, 16, 335-342. (b) Åkermark, B.; Zetterberg, K. J. Am. Chem. Soc. 1984, 106, 5560-5561. (c) Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 106, 7122-7126.
28. Examples of trans-aminopalladation are well documented. For leading references, see: (a) Bäckvall, J.-E. Acc. Chem. Res. 1983, 16, 335-342. (b) Åkermark, B.; Zetterberg, K. J. Am. Chem. Soc. 1984, 106, 5560-5561. (c) Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 106, 7122-7126.
29. Examples of trans-aminopalladation are well documented. For leading references, see: (a) Bäckvall, J.-E. Acc. Chem. Res. 1983, 16, 335-342. (b) Åkermark, B.; Zetterberg, K. J. Am. Chem. Soc. 1984, 106, 5560-5561. (c) Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 106, 7122-7126.
30. For examples of anti-β-hydride elimination, see: Ikeda, M.; El Bialy, S. A. A.; Yakura, T. Heterocycles 1999, 51, 1957-1970.
31. (a) Sparke, M. B.; Turner, L.; Wenham, A. J. M. J. Catal. 1965, 4, 332-340.
32. (b) Sen, A.; Lai, T. W. Inorg. Chem. 1984, 23, 3257-3258.