A novel one-pot three-component synthesis of 3-halofurans and sequential Suzuki coupling

Chemical Communications

Volumn , Issue 20, 2005, Pages 2581-2583

  Karpov, Alexei S ^a   Merkul, Eugen ^a   Oeser, Thomas ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; HALOGENATED HYDROCARBON;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; POLYMERIZATION; SONOGASHIRA REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 20444457114     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b502324f     Document Type: Article

References (25)

1. B. A. Keay and P. W. Dibble, in Comprehensive Heterocyclic Chemistry II, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Elsevier, Oxford, 1997, vol. 2, pp. 395.
2. For pharmaceuticals, see e.g.: D. S. Mortensen, A. L. Rodrigues, K. E. Karlson, J. Sun, B. S. Katzenellenbogen and J. A. Katzenellenbogen, J. Med. Chem., 2001, 44, 3838.
3. C. Liu and T. Luh, Org. Lett., 2002, 4, 4305.
4. For reviews, see e.g.: R. C. D. Brown, Angew. Chem. Int. Ed., 2005, 44, 850;
5. G. Zeni and R. C. Larock, Chem. Rev., 2004, 104, 2285.
6. For recent reviews, see e.g.: T. L. Gilchrist, J. Chem. Soc., Perkin Trans. 1, 1999, 2849;
7. X. L. Hou, H. Y. Cheung, T. Y. Hon, P. L. Kwan, T. H. Lo, S. Y. Tong and H. N. C. Wong, Tetrahedron, 1998, 54, 1955.
8. For Pd-catalyzed transformations of acyclic precursors to furans, see e.g.: A. Jeevanandam, A. Ghule and Y.-C. Ling, Curr. Org. Chem., 2002, 6, 841;
9. D. K. Barma, A. Kundu, R. Baati, C. Mioskowski and J. R. Falck, Org. Lett., 2002, 4, 1387.
10. For investigations on cross-coupling of halofurans, see e.g.: M. W. Hooper and J. F. Hartwig, Organometallics, 2003, 22, 3394.
11. For the preparation of 3-lithiofuran, see e.g.: C. C. Bond and M. Hooper, Synthesis, 1974, 443.
12. For the recent synthesis of 3-substituted 4-chlorofurans, see e.g.: R. N. Ram and I. Charles, Chem. Commun., 2003, 2267.
13. For the recent synthesis and further transformations of β-iodofurans, see e.g.: G. M. M. El-Taeb, A. B. Evans, S. Jones and D. W. Knight, Tetrahedron Lett., 2001, 42, 5945;
14. C. Schultz-Fademrecht, M. Zimmermann, R. Fröhlich and D. Hoppe, Synlett, 2003, 1969;
15. S. P. Bew and D. W. Knight, Chem. Commun., 1996, 1007.
16. A. S. Karpov, T. Oeser and T. J. J. Müller, Chem. Commun., 2004,1502;
17. A. S. Karpov and T. J. J. Müller, Synthesis, 2003, 2815;
18. A. S. Karpov and T. J. J. Müller, Org. Lett., 2003, 5, 3451.
19. For heterocycle synthesis from ynones, see e.g.: M. C. Bagley, D. D. Hughes and P. H. Taylor, Synlett, 2003, 259;
20. C. G. Savarin, J. A. Murry and P. G. Dormer, Org. Lett., 2002, 4, 2071.
21. The successful conversion of γ-hydroxy alkynones into halofurans has been reported by: D. Obrecht, Helv. Chim. Acta, 1989, 72, 447.
22. 11IO: 297.9855. Found: 297.9861.
23. For excellent recent reviews, see e.g.: A. Ajamian and J. L. Gleason, Angew. Chem. Int. Ed, 2004, 43, 3754;
24. J. M. Lee, Y. Na, H. Ran and S. Chang, Chem. Soc. Rev., 2004, 33, 302.
25. 2 (250.30): C 81.58, H 5.64. Found: C 81.20, H 5.63.