Microwave-assisted Suzuki-Miyaura couplings on α-iodoenaminones

Tetrahedron Letters

Volumn 48, Issue 50, 2007, Pages 8811-8814

  Wang, Xin ^a   Turunen, Brandon J ^a   Leighty, Matthew W ^a   Georg, Gunda I ^a  

^a Library Development   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA IODOENAMINONE DERIVATIVE; AMINE; AROMATIC BORONIC ACID DERIVATIVE; BORONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALPHA IODINATION; ARTICLE; CHEMICAL MODIFICATION; HEATING; IODINATION; MICROWAVE RADIATION; PRODUCT RECOVERY; REACTION ANALYSIS; REACTION OPTIMIZATION; SUZUKI MIYAURA COUPLING REACTION; SUZUKI REACTION;

EID: 36049045806     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.078     Document Type: Article

References (34)

1. Turunen B.J., and Georg G.I. J. Am. Chem. Soc. 128 (2006) 8702
2. For recent reviews, see:. Negri G., Kascheres C., and Kascheres A.J. J. Heterocycl. Chem. 41 (2004) 461
3. Elassar A.-Z.A., and El-Khair A.A. Tetrahedron 59 (2003) 8463
4. Michael J.P., De Koning C.B., Gravestock D., Hosken G.D., Howard A.S., Jungmann C.M., Krause R.W.M., Parsons A.S., Pelly S.C., and Stanbury T.V. Pure Appl. Chem. 71 (1999) 979
5. Comins D.L. J. Heterocycl. Chem. 36 (1999) 1491
6. During the course of our investigation an example of iodination and Suzuki-Miyaura coupling of an N-arabinosyl dehydropiperidinone appeared. Kranke B., and Kunz H. Can. J. Chem. 84 (2006) 625
7. Kranke B., and Kunz H. Org. Biomol. Chem. 5 (2007) 349
8. Suzuki A. J. Organomet. Chem. 576 (1999) 147
9. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
10. Fitzmaurice R.J., Etheridge Z.C., Jumel E., Woolfson D.N., and Caddick S. Chem. Commun. (2006) 4814
11. Kappe O.C. Angew. Chem., Int. Ed. 43 (2004) 6250
12. Kellogg R.M. Chemtracts 17 (2004) 451
13. Song Y.S., Kim B.T., and Heo J.-N. Tetrahedron Lett. 46 (2005) 5987
14. Song Y.S., Lee Y.-J., Kim B.T., and Heo J.-N. Tetrahedron Lett. 47 (2006) 7427
15. Kim J.M., Na J.E., and Kim J.N. Tetrahedron Lett. 44 (2003) 6317
16. Ohshima T., Xu Y., Takita R., and Shibasaki M. Tetrahedron 60 (2004) 9569
17. Sha C.-K., Shen C.-Y., Jean T.-S., Chiu R.-T., and Tseng W.-H. Tetrahedron Lett. 34 (1993) 7641
18. Sha C.-K., Santhosh K.C., Tseng C.-T., and Lin C.-T. J. Chem. Soc., Chem. Commun. (1998) 397
19. Campos P.J., Arranz J., and Rodriguez M.A. Tetrahedron Lett. 38 (1997) 8397
20. Matsuo K., Ishida S., and Takuno Y. Chem. Pharm. Bull. 42 (1994) 1149
21. Kordik C.P., and Reitz A.B. J. Org. Chem. 61 (1996) 5644
22. Ramesh N.G., Heijne E.H., Klunder A.J.H., and Zwanenburg B. Tetrahedron Lett. 39 (1998) 3295
23. Ramesh N.G., Heijne E.H., Klunder A.J.H., and Zwanenburg B. Tetrahedron 58 (2002) 1361
24. Papoutsis I., Spyroudis S., Varvoglis A., Callies J.A., and Zhdankin V.V. Tetrahedron Lett. 38 (1997) 8401
25. For an example of a bromodesilylation on an unprotected enaminone, see:. Comins D.L., Chen X., and Morgan L.A. J. Org. Chem. 62 (1997) 7435
26. Johnson C.R., Adams J.P., Braun M.P., Senanayake C.B.W., Wovkulich P.M., and Uskokovic M.R. Tetrahedron Lett. 33 (1992) 917
27. 11INO: 263.9885, found 263.9886.
28. 3N in EtOAc) to provide the desired α-iodoenaminone 1a (95%).
29. 13INO: 278.0036, found 278.0038.
30. Comins D.L., Joseph S.P., and Chen X. Tetrahedron Lett. 36 (1995) 9141
31. Felpin F.-X. J. Org. Chem. 70 (2005) 8575
32. Cordell G.A. The Alkaloids: Chemistry and Biology Vol. 60 (2003), Elsevier
33. 3: 274.1443, found 274.1441.
34. 3N in EtOAc) to provide 187 mg of the title compound (75%).