Water as nucleophile in palladium-catalyzed oxidative carbohydroxylation of allene-substituted conjugated dienes

Journal of the American Chemical Society

Volumn 129, Issue 46, 2007, Pages 14120-14121

  Piera, Julio ^a   Persson, Andreas ^a   Caldentey, Xisco ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; ALKADIENE; ALLENE DERIVATIVE; PALLADIUM; SOLVENT; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; HECK REACTION; HYDROXYLATION; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 36448980297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075488j     Document Type: Article

References (44)

1. (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
2. (b) Li, C.-J. Chem. Rev. 2005, 105, 3095.
3. (c) Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68.
4. See for example: (a) Lautens, M.; Tayama, E.; Herse, C. J. Am. Chem. Soc. 2005, 127, 72.
5. (b) Arvela, R. K.; Leadbeater, N. E. Org. Lett. 2005, 7, 2101.
6. (c) Mariampillai, B.; Herse, C.; Lautens, M. Org. Lett. 2005, 7, 4745.
7. (d) Liu, L.; Zhang, Y.; Wang, Y. J. Org. Chem. 2005, 70, 6122.
8. (e) Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173.
9. (a) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921.
10. (b) Kogan, V.; Aizenshtat, Z.; Popovitz-Biro, R.; Neumann, R. Org. Lett. 2002, 4, 3529.
11. (c) Botella, L.; Nájera, C. Tetrahedron 2004, 60, 5563.
12. See for example: (a) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919.
13. (b) Manabe, K.; Kobayashi, S. Org. Lett. 2003, 5, 3241.
14. (c) Chevrin, C.; Le Bras, J.; Hénin, F.; Muzart, J.; Pla-Quintana, A.; Roglans, A.; Pleixats, R. Organometallics 2004, 23, 4796.
15. (d) Kinoshita, H.; Shinokubo, H.; Oshima, K. Org. Lett. 2004, 6, 4085.
16. See for example: (a) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636.
17. (b) ten Brink, G.-J.; Arends, I. W. C. E.; Hoogenraad, M.; Verspui, G.; Sheldon, R. A. Adv. Synth. Catal. 2003, 345, 1341.
18. (c) Uozumi, Y.; Nakao, R. Angew. Chem., Int. Ed. 2003, 42, 194.
19. See for example: (a) Bäckvall, J. E.; Åkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411.
20. (b) ten Brink, G.-J.; Arends, I. W. C. E.; Papadogianakis, G.; Sheldon, R. A. Chem. Commun. 1998, 2359.
21. - on a (π-allyl)palladium complex, see: Nilsson, Y. I. M.; Aranyos, A.; Andersson, P. G.; Bäckvall, J. E.; Parrain, J. L.; Ploteau, C.; Quintard, J. P. J. Org. Chem. 1996, 61, 1825.
22. Trost, B. M.; McEachern, E. J. J. Am. Chem. Soc. 1999, 121, 8649.
23. Trost, B. M.; Ito, N.; Greenspan, P. D. Tetrahedron Lett. 1993, 34, 1421.
24. (a) Modem Oxidation Methods; Bäckvall, J. E., Ed.; Wiley-VCH: Weinheim, Germany, 2004.
25. (b) Trost, B. M.; Fleming, I. A. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991.
26. (a) Piera, J.; Bäckvall, J. E. Angew. Chem. Int. Ed. In press,
27. (b) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400.
28. For a few C-C bond forming aerobic reactions in organic solvents, see: (a) Trend, R. M.; Ramtohul, Y. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 17778.
29. (b) Dams, M.; De Vos, D. E.; Selen, S.; Jacobs, P. A. Angew. Chem., Int. Ed. 2003, 42, 3512.
30. (c) For a recent interesting non-aerobic oxidation with C-C bond formation via outer sphere nucleophilic attack of indole on an (olefin)palladium complex, see: Liu, C.; Widenhoefer, R. A. Chem. - Eur. J. 2006, 12, 2371.
31. (a) Löfstedt, J.; Franzén, J.; Bäckvall, J. E. J. Org. Chem. 2001, 66, 8015.
32. (b) Löfstedt, J.; Närhi, K.; Dorange, I.; Bäckvall, J. E. J. Org. Chem. 2003, 68, 7243.
33. (c) Dorange, I.; Löfstedt, J.; Närhi, K.; Franzén, J.; Bäckvall, J. E. Chem. - Eur. J. 2003, 9, 3445.
34. (a) Franzén, J.; Bäckvall, J. E. J. Am. Chem. Soc. 2003, 125, 6056.
35. (b) Piera, J.; Närhi, K.; Bäckvall, J. E. Angew. Chem., Int. Ed. 2006, 45, 6914.
36. For the optimization of the reaction, see the Supporting Information.
37. Solid reactants can be used in pure water when the rest of the reagents are liquids, but not when all the components are solids. See for example: Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275.
38. Similar coupled catalytic systems have been previously used by our group in 1,4-oxidation of dienes and in allylic oxidations: (a) Bäckvall, J.-E.; Hopkins, R. B.; Grennberg, H.; Mader, M.; Awasthi, A. K. J. Am. Chem. Soc. 1990, 112, 5160.
39. (b) Wöltinger, J.; Bäckvall, J.-E.; Zsigmond, A. Chem. - Eur. J. 1999, 5, 1460.
40. (c) Reference 14b.
41. The stereochemistry of compound 2a was established by converting it to the known acetate (see ref 13a).
42. 1H NMR, which shows that the first step is formation of vinyl complex A (see Supporting Information). Insertion of the diene to give allyl intermediates requires BQ, and C-O bond formation is the last step of the sequence.
43. 2 as catalyst gave 80% yield of 2a, and the allylic acetate is completely stable under the reaction conditions.
44. Karlsson, E. A.; Bäckvall, J. E. Unpublished results.