Microwave-assisted palladium-catalyzed cross-coupling reactions between pyranoid glycals and aryl bromides. Synthesis of 2′-deoxy C-aryl-β-glycopyranosides

Tetrahedron Letters

Volumn 50, Issue 36, 2009, Pages 5135-5138

  Lei, Ming ^a   Gao, Liang ^a   Yang, Jin Song ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Aryl bromide; Aryl C glycoside; Glycal; Microwave

Indexed keywords

2,3 DICHLORO 5,6 DICYANOBENZOQUINONE; BENZOQUINONE DERIVATIVE; BROMIDE; CHLORINE DERIVATIVE; GLYCOPYRANOSIDE; N,N DIMETHYLFORMAMIDE; PALLADIUM ACETATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CONFORMATION; CROSS COUPLING REACTION; MICROWAVE IRRADIATION; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; REDUCTION; STEREOCHEMISTRY;

EID: 67650599488     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.116     Document Type: Article

References (33)

1. Hansen M.R., and Hurley L.H. Acc. Chem. Res. 29 (1996) 249-258
2. Bililign T., Griffith B.R., and Thorson J.S. Nat. Prod. Rep. 22 (2005) 742-760 and references therein
3. Du Y.-G., and Linhardt R.J. Tetrahedron 54 (1998) 9913-9959
4. Suzuki K., and Matsumoto T. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Dekker, New York 527-542
5. Frappa I., and Sinou D. J. Carbohydr. Chem. 16 (1997) 255-276
6. Daves Jr. G.D. Acc. Chem. Res. 23 (1990) 201-206
7. Matsumoto T., Katsuki M., and Suzuki K. Tetrahedron Lett. 30 (1989) 833-836
8. Schmidt R.R., and Hoffman M. Tetrahedron Lett. 23 (1982) 409-412
9. Kometani T., Kondo H., and Fujimori Y. Synthesis (1988) 1005-1007
10. Matsumoto T., Katsuki M., and Suzuki K. Tetrahedron Lett. 29 (1988) 6935-6938
11. Matsumoto T., Katsuki T., Jona H., and Suzuki K. J. Am. Chem. Soc. 113 (1991) 6982-6992
12. Mahling J.A., and Schmidt R.R. Synthesis (1993) 325-328
13. Vu N.Q., Leconte S., Brown E., Grée D., Grée R., and Dujardin G. J. Org. Chem. 70 (2005) 2641-2650
14. Schmidt R.R., Frick W., Haag-Zeino B., and Apparao S. Tetrahedron Lett. 28 (1987) 4045-4048
15. Hauser F.M., and Hu X. Org. Lett. 3 (2002) 2977-2980
16. Calimente D., and Postema M.H.D. J. Org. Chem. 64 (1999) 1770-1771
17. Schmidt B. Org. Lett. 2 (2000) 791-794
18. Hart D.J., Merriman G.H., and Young D.G.J. Tetrahedron 52 (1996) 14437-14458
19. Zhang H.-C., and Daves Jr. G.D. J. Org. Chem. 58 (1993) 2557-2560
20. Zhang H.-C., and Daves Jr. G.D. J. Org. Chem. 57 (1992) 4690-4696
21. Farr R.N., Kwok D.-I., and Daves Jr. G.D. J. Org. Chem. 57 (1992) 2093-2100
22. Kwok D.-I., Farr R.N., and Daves Jr. G.D. J. Org. Chem. 56 (1991) 3711-3713
23. Farr R.N., Outten R.A., Cheng J.C.-Y., and Daves Jr. G.D. Organometallics 9 (1990) 3151-3156
24. For a recent review on Pd-catalyzed reactions promoted by microwave, see:. Barge A., Tagliapietra S., Tei L., Cintas P., and Cravotto G. Curr. Org. Chem. 12 (2008) 1588-1612
25. Ferrier R. J. Chem. Soc. (1964) 5443-5449
26. Ferrier R., and Prasad N. J. Chem. Soc. C (1969) 570-575
27. Toshima K., Miyamoto N., Matsuo G., Nakata M., and Matsumura S. Chem. Commun. (1996) 1379-1380
28. 4, and concentrated. The crude material was purified by flash column chromatography on silica gel eluted with petroleum ether/EtOAc to afford the 2′,3′-unsaturated C-aryl-α-glycopyranosides 2a-j.
29. Friesen R.W., Loo R.W., and Sturino C.F. Can. J. Chem. 74 (1994) 1262-1272
30. Lehmann U., Awasthi S., and Minehan T. Org. Lett. 5 (2003) 2405-2408
31. Danishefsky S., and Kerwin Jr. J.F. J. Org. Chem. 47 (1982) 3803-3805
32. Brakta M., Farr R.N., Chaguir B., Massiot G., Lavaud C., Anderson Jr. W.R., Sinou D., and Daves Jr. G.D. J. Org. Chem. 58 (1993) 2992-2998
33. 1′-arylated enone acetates, see:. Benhaddou R., Czernecki S., and Ville G. J. Org. Chem. 57 (1992) 4612-4616