Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. Synthesis of C-aryl glycals

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2405-2408

  Lehmann, Ute ^a   Awasthi, Smita ^a   Minehan, Thomas ^a  

^a HARVEY MUDD COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BROMINE DERIVATIVE; GLUCONATE CALCIUM; HALIDE; IODIDE; IODINE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAN DERIVATIVE; REAGENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CROSS COUPLING REACTION; ELECTRON; SYNTHESIS;

EID: 0141854965     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0345428     Document Type: Article

References (37)

1. (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
2. (b) Tsuji, J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: Chichester, U.K., 1996.
3. (c) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: New York, 1985.
4. (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998.
5. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
6. (c) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771.
7. (d) Pereye, M.; Quintard, J.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
8. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
9. (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 2, p 49.
10. Negishi, E. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; Oxford University Press: Oxford, U.K., 1999; Chapter 11.
11. (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
12. (b) Li, C.-J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
13. (c) Grieco, P. A. Organic Synthesis in Water; Blackie Academic & Professional: London, 1998.
14. (d) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149.
15. (a) Perez, I.; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001, 123, 4155.
16. (b) Perez, I.; Sestelo, J. P.; Sarandeses, L. A. Org. Lett. 1999, 1, 1267. See also: Nomura, R.; Miyazaki, S.-I.; Matsuda, H. J. Am. Chem. Soc. 1992, 114, 2738.
17. (b) Perez, I.; Sestelo, J. P.; Sarandeses, L. A. Org. Lett. 1999, 1, 1267. See also: Nomura, R.; Miyazaki, S.-I.; Matsuda, H. J. Am. Chem. Soc. 1992, 114, 2738.
18. Takami, K.; Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. Org. Lett. 2001, 3, 1997.
19. Anastas, P. T.; Warner, J. C. Green Chemistry; Oxford University Press: Oxford, 1998; p 29.
20. For previous examples of cross-coupling reactions of tetrahydropyranyl organometallics, see ref 11 and also: Mazal, C.; Vaultier, M. Tetrahedron Lett. 1994, 35, 3089.
21. (a) Boeckman, R. J.; Bruza, K. J. Tetrahedron Lett. 1977, 18, 4187.
22. (b) Boeckman, R. J.; Bruza, K. J. Tetrahedron 1981, 37, 3997.
23. Denmark, S. E.; Neuville, L. Org. Lett. 2000, 2, 3221.
24. Friesen, R. W.; Loo, R. W.; Sturino, C. F. Can. J. Chem. 1994, 74, 1262.
25. Formed by addition of lithiodihydropyran to a THF solution of 0.5 equiv of indium trichloride.
26. Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228.
27. (a) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 2000, 122, 402.
28. (b) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 8214.
29. (a) Parker, K. A.; Georges, A. T. Org. Lett. 2000, 2, 491.
30. (b) Parker, K. A.; Coburn, C. A. J. Org. Chem. 1992, 57, 5547.
31. (c) Friesen, R. W.; Sturino, C. F. J. Org. Chem. 1990, 55, 5808.
32. (d) Friesen, R. W.; Daljeet, A. K. Tetrahedron Lett. 1990, 31, 6133.
33. (e) Dubois, E.; Beau, J. M. Tetrahedron Lett. 1990, 31, 5165.
34. (d) Dubois, E.; Beau, J. M. Carbohydr. Res. 1992, 223, 157.
35. Friesen, R. W.; Sturino, C. F.; Daljeet, A. K.; Kolaczewska, A. J. Org. Chem. 1991, 56, 1944.
36. 3) in an attempt to improve yields in this process; although these reactions in some cases proceed to completion in shorter times (4 vs 24 h), the overall yields did not change significantly from those reported in Table 2.
37. Friesen, R. W.; Daljeet, A. K. Tetrahedron Lett. 1990, 31, 6133.