Distinct reactivity of Pd(OTs)2: The intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes

Journal of the American Chemical Society

Volumn 130, Issue 31, 2008, Pages 10066-10067

  Houlden, Chris E ^a   Bailey, Chris D ^a   Ford, J Gair ^b   Gagné, Michel R ^c   Lloyd Jones, Guy C ^a   Booker Milburn, Kevin I ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE; ALKADIENE; ALPHA METHYLSTYRENE; AMIDE; PALLADIUM; PALLADIUM COMPLEX; UREA DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DIASTEREOISOMER; ELECTRON; OXIDATION; SENSITIVITY ANALYSIS; SYNTHESIS;

AMINATION; CATALYSIS; INDOLES; PALLADIUM; POLYENES; SULFONAMIDES; TOLUENE; UREA;

EID: 48749120080     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803397y     Document Type: Article

References (33)

1. (a) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580.
2. (b) Kotti, S. R. S. S.; Timmons, C.; Li, G. Chem. Biol. Drug. Des. 2006, 67, 101.
3. (a) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
4. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
5. (a) Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250.
6. (b) Yuan, W.; Du, H.; Zhao, B.; Shi, Y. Org. Lett. 2007, 9, 2589.
7. (a) Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586.
8. (b) Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762.
9. (c) Muniz, K.; Hövelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763.
10. Bar, G. L. J.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2005, 127, 7308.
11. For formation of indolines by Pd(0) cat. oxidative addition of o-halo anilines to dienes, see:(a) Larock, R. C.; Berrios-Pena, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447.
12. (b) Larock, R. C. J. Organomet. Chem. 1999, 576, 111.
13. (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
14. (b) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35.
15. (c) Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 7, 949.
16. Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
17. 2/tBuOOH see : Jia, C.; Lu, W.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097.
18. Drent, E.; van Broekhoven, J. A. M.; Doyle, M. J. J. Organomet. Chem. 1991, 417, 235.
19. (a) Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984, 106, 5759.
20. (b) Yokoyama, Y.; Takashima, M.; Higaki, C.; Shidori, K.; Moriguchi, S; Ando, C.; Murakami, Y. Hetercycles 1993, 36, 1739.
21. (c) Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211.
22. (d) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
23. (e) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
24. (f) Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528.
25. (g) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
26. (h) Shi, Z.; Li, B.; Wan, X.; Cheng, J.; Fang, Z.; Cao, B.; Qin, C.; Wang, Y. Angew. Chem., Int. Ed. 2007, 46, 5554.
27. (i) Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
28. (j) Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904.
29. (k) Wang, J.-R.; Yang, C.-T.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 5449.
30. (l) Zhang, Y.; Feng, J.; Li, C.-J. J. Am. Chem. Soc. 2008, 130, 2900.
31. (m) Yang, S.-D.; Sun, C.-L.; Fang, Z.; Li, B.-J.; Li, Y.-Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1473.
32. (n) Lebrasseur, N.; Larrosa, I. J. Am. Chem. Soc. 2008, 130, 2926.
33. (o) Brasche, G.; Garcia-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207.