Microwave-Promoted and Chelation-Controlled Double Arylations of Terminal Olefinic Carbon of Vinyl Ethers

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3345-3349

  Svennebring, Andreas ^a   Nilsson, Peter ^a   Larhed, Mats ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; CHELATION; MICROWAVE HEATING; PALLADIUM; STEREOCHEMISTRY;

ARYLATIONS; PRECATALYSTS;

ETHERS;

ALKENE; CARBON; ETHER DERIVATIVE; N,N DIMETHYL (2 ETHENYLOXY)ETHANAMINE; N,N DIMETHYL 2 [(2,2 DI 4 ANISYL)ETHENYLOXY]ETHANAMINE; N,N DIMETHYL 2 [[2 PHENYL 2 (2 NAPHTHYL)]ETHENYLOXY]ETHANAMINE; PALLADIUM; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHELATION; CHEMICAL REACTION; ELECTRON; ENERGY; GAS CHROMATOGRAPHY; HEATING; HECK REACTION; HIGH TEMPERATURE PROCEDURES; MASS SPECTROMETRY; MICROWAVE RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 2442588634     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035815f     Document Type: Article

References (30)

1. Herrmann, W. A.; Bohm, V. P. W.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23-41.
2. Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314-321.
3. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
4. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
5. Braese, S.; De Meijere, A. Double and Multiple Heck Reactions. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley & Sons: New York, 2002; Vol. 1, pp 1179-1208.
6. Larhed, M.; Hallberg, A. Scope, Mechanism, and Other Fundamental Aspects of the Intermolecular Heck Reaction. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; Wiley & Sons: New York, 2002; Vol. 1, pp 1133-1178.
7. Gurtler, C.; Buchwald, S. L. Chem.-Eur. J. 1999, 5, 3107-3112.
8. Sugihara, T.; Takebayashi, M.; Kaneko, C. Tetrahedron Lett. 1995, 36, 5547-5550.
9. Larhed, M.; Andersson, C.-M.; Hallberg, A. Tetrahedron 1994, 50, 285-304.
10. Itami, K.; Nokami, T.; Yoshida, J. Org. Lett. 2000, 2, 1299-1302.
11. Alonso, I.; Carretero, J. C. J. Org. Chem. 2001, 66, 4453-4456.
12. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2003, 125, 3430-3431.
13. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217-8225.
14. Lednicer, D. Strategies for Organic Drug Synthesis and Design, 1st ed.; Wiley & Sons: New York, 1998.
15. Andersen, K. E.; Sorensen, J. L.; Huusfeldt, P. O.; Knutsen, L. J. S.; Lau, J.; Lundt, B. F.; Petersen, H.; Suzdak, P. D.; Swedberg, M. D. B. J. Med. Chem. 1999, 42, 4281-4291.
16. Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727.
17. Olofsson, K.; Hallberg, A.; Larhed, M. In Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley & Sons: Weinheim, Germany, 2002; pp 379-403.
18. Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
19. Kaiser, N. F. K.; Bremberg, U.; Larhed, M.; Moberg, C.; Hallberg, A. Angew. Chem., Int. Ed. 2000, 39, 3596-3598.
20. trans-Di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II). Registry number provided by the author: 172418-32-5.
21. Shaw, B. L. New J. Chem. 1998, 22, 77-79.
22. Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29-35.
23. Bedford, R. B. Chem. Commun. 2003, 1787-1796.
24. Wan, Y. Q.; Alterman, M.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6232-6235.
25. Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536.
26. For selectivity values with the different catalytic systems, see the Supporting Information.
27. Herrmann, W. A.; Brossmer, C.; Reisinger, C. P.; Riermeier, T. H.; Ofele, K.; Beller, M. Chem.-Eur. J. 1997, 3, 1357-1364.
28. Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 1848-1855.
29. de Vries, A. H. M.; Mulders, J.; Mommers, J. H. M.; Henderickx, H. J. W. ; de Vries, J. G. Org. Lett. 2003, 5, 3285-3288.
30. Consorti, C. S.; Zanini, M. L.; Leal, S.; Ebeling, G.; Dupont, J. Org. Lett. 2003, 5, 983-986.