Intramolecular palladium-catalyzed direct arylation of alkenyl triflates

Organic Letters

Volumn 9, Issue 21, 2007, Pages 4391-4393

  Cruz, Ana C F ^a   Miller, Neil D ^c   Willis, Michael C ^b  

^a University of Bath   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; MESYLIC ACID DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY;

ALKENES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MESYLATES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 35548943629     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702044z     Document Type: Article

References (33)

1. General reviews: (a) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-L, Ed.; Wiley: New York, 2002.
2. (b) Metal-Catalysed Cross-Coupling Reactions; de Meijere, A., Deidrich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
3. For general reviews on C-H functionalization, see: (a) Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
4. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
5. (c) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
6. For recent examples of Pd-catalyzed cross-coupling processes in which both activating groups are absent, see: (a) Stuart, D. R.; Fagnou, K., Science 2007, 316, 1172.
7. (b) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137.
8. (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
9. (b) Campeau, L.-G; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35.
10. (c) Campeau, L.-C.; Fagnou, K. Chem. Commun. 2005, 1253.
11. Selected examples: (a) Ames, D. E.; Opalko, A. Synthesis 1983, 234.
12. (b) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2.
13. (c) Li, W. J.; Nelson, D. P.; Jensen, M. S.; Hoerrner, R. S.: Javadi, G. J.; Cai, D.; Larsen, R. D. Org. Lett. 2003, 5, 4835.
14. (d) Touré, B. B.; Lane, B. S.; Sames, D. Org. Lett. 2006, 8, 1979.
15. (a) LaFrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
16. (b) LaFrance, M.; Shore, D.; Fagnou Org. Lett. 2006, 8, 5097.
17. (a) Campeau, L.-C.; Thansandote, P.; Fagnou, K. Org. Lett. 2005, 7, 1857.
18. (b) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
19. (c) LaFrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
20. Directed arylation reactions have been achieved with a variety of electronically varied arenes. For a discussion of directed arylation systems, as well as the use of alternative metal catalysts, see ref 4a.
21. (a) Hughes, C. C.; Trauner, D. Angew. Chem., Int. Ed. 2002, 47, 1569;
22. Angew. Chem., Int. Ed. 2002, 41, 2227 (erratum).
23. (b) Hughes, C. C.; Trauner, D. Tetrahedron 2004, 60, 9675.
24. (c) Fishwick, C. W. G.; Grigg, R.; Sridharan, V.; Virica, J. Tetrahedron 2003, 59, 4451.
25. (d) Ackermann, L.; Althammer, A. Angew. Chem., Int. Ed. 2007, 46, 1627.
26. See Supporting Information for details.
27. (a) Willis, M. C.; Powell, L. H. W.; Claverie, C. K.; Watson, S. J. Angew. Chem., Int. Ed. 2004, 42, 1249.
28. (b) Willis, M. C.; Claverie, C. K.; Mahon, M. F. Chem. Commun. 2002, 832.
29. Echavarren, A. M.; Gómez-Lor, B.; González, J. J.; de Frutos, Ó. Synlett 2003, 58. See also ref 4a.
30. Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
31. Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084.
32. (a) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
33. (b) Garcia-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880. See also ref 7c.