Direct measurement of the thermodynamics of vinylarene hydroamination

Journal of the American Chemical Society

Volumn 128, Issue 29, 2006, Pages 9306-9307

  Johns, Adam M ^a   Sakai, Norio ^a   Ridder, André ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE; POLYCYCLIC AROMATIC HYDROCARBON; TRANSITION ELEMENT; VINYL DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENTHALPY; ENTROPY; EQUILIBRIUM CONSTANT; MEASUREMENT; THERMODYNAMICS;

ALKENES; AMINES; CATALYSIS; THERMODYNAMICS;

EID: 33746366232     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja062773e     Document Type: Article

References (43)

1. (a) Haggin, J. Chem. Eng. News 1993, 23.
2. (b) Roesky, P. W.; Muller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708.
3. (c) Nobis, M.; Driessen-Holscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983.
4. (d) Hultzsch, K. C. Org. Biomol. Chem. 2005, 3, 1819.
5. (e) Brunei, J. J. Gazz. Chim. Ital. 1997, 127, 111.
6. (f) Gase, M. B.; Lattes, A.; Perie, J. J. Tetrahedron 1983, 39, 703.
7. (g) Casalnuovo, A. L.; Calabrese, J. C.; Mustern, D. J. Am. Chem. Soc. 1988, 110, 6738.
8. (h) Coulson, D. R. Tetrahedron Lett. 1971, 429.
9. (a) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayacl, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 1579.
10. (b) Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367.
11. (c) Muller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
12. (a) Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Herwig, J.; Muller, T. E.; Thiel, O. R. Chem.-Eur. J. 1999, 5, 1306.
13. (b) Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070.
14. (c) Bexrud, J. A.; Beard, J. D.; Leitch, D. C.; Schafer, L. L. Org. Lett. 2005, 7, 1959.
15. (d) Bieler, N.; Egli, P.; Dorta, R.; Togni, A.; Eyer, M.; (Lonza, A. G., Switzerland). EP 909762, 1999.
16. (e) Burgstein, M. R.; Berberich, H.; Roesky, P. W. Organometallics 1998, 17, 1452.
17. (f) Crimmin, M. R.; Casely, I. J.; Hill, M. S. J. Am. Chem. Soc. 2005, 127, 2042.
18. (g) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
19. (h) Kawatsura, M.; Hartwig, J. F. Organometallics 2001, 20, 1960.
20. Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737.
21. (j) Kim, Y. K.; Livinghouse, T.; Horino, Y. J. Am. Chem. Soc. 2003, 125, 9560.
22. (k) Lober, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366.
23. Nettekoven, U.; Hartwia, J. F. J. Am. Chem. Soc. 2002, 124, 1166.
24. Pawlas, J.; Nakao, Y.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 3669.
25. (n) Seayad, J.; Tillack, A.; Hartung, C. G.; Beller, M. Adv. Synth. Catal. 2002, 344, 795.
26. (o) Takaya, J.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 5756.
27. (p) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14286.
28. (q) Utsunomiya, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2702.
29. (r) Wang, X.; Widenhoefer, R. A. Organometallics 2004, 23, 1649.
30. Johns, A. M.; Utsunomiya, M.; Incarvito, C. D.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828.
31. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546.
32. (a) Steinborn, D.; Taube, R. Z. Chem. 1986, 26, 349.
33. (b) R. Taube In Applied Homogeneous Calahsis. 2nd ed.; Cornils, B., Hernnann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 1, p 513.
34. For examples of addition of anilines to norbornene, see: (a) Ackermann, L.; Kaspar, L. T.; Gschrei, C. J. Org. Lett. 2004, 6, 2515.
35. (b) Anderson, L. L.; Arnold, J.; Bergman, R. G. J. Am. Chem. Soc. 2005, 127, 14542.
36. (c) Brunei, J. J.; Chu, N. C; Diallo, O. Organometallics 2005, 24, 3104.
37. (d) Dorta, R.; Egli, P.; Zurcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857.
38. For examples of additions of carboxamides to internal olefins, see: (e) Aufdenblatten, R.; Diezi, S.; Togni, A. Monatsh. Chem. 2000, 131, 1345.
39. (f) Qian, H.; Widenhoefer, R. A. Org. Lett. 2005, 7, 2635.
40. For examples of additions of sulfonamides to internal olefins, see: (g) Karshtedt, D.; Bell, A. T.; Tilley, T. D. J. Am. Chem. Soc. 2005, 127, 12640.
41. (h) Zhang, J. L.; Yang, C. G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798.
42. 1H NMR spectroscopy.
43. March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992.