Palladium-Catalyzed Three-Component coupling reactions: 1,1 -Difunctionalization of activated alkenes

European Journal of Organic Chemistry

Volumn , Issue 9, 2009, Pages 1313-1316

  Rodriguez, Arantxa ^a   Moran, Wesley J ^a  

^a UNIVERSITY OF HUDDERSFIELD   (United Kingdom)

Author keywords

C C coupling; C H activation; Heck reaction; Iodine; Palladium

Indexed keywords

EID: 63449097834     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801245     Document Type: Article

References (36)

1. For an excellent review on Pd∏-catalyzed reactions involving oxidants, see: E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318.
2. a) K. Muniz, C. H. Hovelmann, J. Streuff, J. Am. Chem. Soc. 2008, 130, 763;
3. b) J. Streuff, C. H. Hovelmann, M. Nieger, K. Muniz, J. Am. Chem. Soc. 2005, 127, 14586.
4. a) L, V. Desai, M. S. Sanford, Angew. Chem. 2007, 119, 5839;
5. Angew. Chem. Int. Ed. 2007, 46, 5737;
6. b) G. Liu, S. S. Stahl, J. Am, Chem. Soc. 2006, 128, 7179;
7. c) E.J. Alexanian, C. Lee, E. J. Sorensen, J. Am. Chem. Soc. 2005, 127, 7690.
8. M. Hayashi, H. Takezaki, Y. Hashimoto, K. Takaoki, K. Saigo, Tetrahedron Lett. 1998, 39, 7529.
9. a) Y. Li, D. Song, V. M. Dong, J. Am. Chem. Soc. 2008, 130, 2962;
10. b) Y. Zhang, M. S. Sigman, J. Am. Chem. Soc. 2007, 129, 3076.
11. a) M. Tani, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 1221;
12. b) T. Yokota, M. Tani, S. Sakaguchi, Y. Ishii, J. Am, Chem. Soc. 2003, 125, 1476;
13. c) M. Dams, D. E. De Vos, S. Celen, P. A. Jacobs, Angew. Chem. Int. Ed. 2003, 42, 3512;
14. Angew. Chem. 2003, 115, 3636;
15. d) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. deVries, P.C.J. Kamer, J. G. deVries, P. W. N. M. van Leeuwen, .J Am. Chem. Soc. 2002, 124, 1586;
16. e) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633;
17. f) C. Jia, W. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097;
18. g) Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166.
19. M. Portnoy, D. Milstein, Organometallics 1994, 13, 600.
20. For examples of sequential coupling reactions involving C-H functionalization, see: a) B.-J. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. Int. Ed. 2008, 47, 1115;
21. Angew. Chem. 2008, 120, 1131;
22. b) L. Ackermann, A. Althammer, Angew. Chem. Int. Ed. 2007, 46, 1627;
23. Angew. Chem. 2007, 119, 1652;
24. c) C.-G. Dong, Q.-S. Hu, Angew. Chem, Int. Ed. 2006, 45, 2289;
25. Angew. Chem. 2006, 118, 2347.
26. a) Y. Tamaru, M. Hojo, S.-I. Kawamura, Z.-I. Yoshida, J. Org. Chem. 1986, 51, 4089;
27. b) D. Kalyani, M. S. Sanford, J. Am. Chem. Soc. 2008, 130, 2150.
28. 2.
29. The reactions can be performed with just one equivalent of oxidant; however, sometimes they stall; the addition of an excess amount of oxidant prevents this from happening.
30. 2 provided no improvement in yields for these substrates.
31. The enantioselective organocatalytic epoxidation of a, β-unsaturated aldehydes with the use of hypervalent iodine reagents has recently been reported: S. Lee, D. W. C. MacMillan, Tetrahedron 2006, 62, 11413.
32. P. J. Stang, M. Boehshar, H. Wingert, T. Kitamura, J. Am. Chem. Soc. 1988, 110, 3272.
33. A number of other mechanisms could be proposed; however, experimentation appears to rule out a Heck-type process followed by conjugate addition of acetate (all attempts to add acetate to ethyl cinnamate were unsuccessful), and the addition of radical inhibitors does not affect the outcome of the reaction, ruling out a radical pathway.
34. IV by acetate with inversion of configuration has been proposed: a) L. L. Welbes, T. W. Lyons, K. A. Cychosz, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 5836;
35. b) X. long. M. Beller, M. K. Tse, J. Am. Chem. Soc. 2007, 129, 4906.
36. For the Pd-catalyzed conjugate addition of acetic acid to en-ones, see: T. Hosokawa, T. Shinohara, Y. Ooka, S.-L Mura-hashi, Chem. Lett. 1989, 2001.