Hypervalent phenyl-λ3-iodane-mediated para-selective aromatic fluorination of 3-phenylpropyl ethers

Chemical Communications

Volumn 47, Issue 12, 2011, Pages 3410-3412

  Saito, Motomichi ^a   Miyamoto, Kazunori ^a   Ochiai, Masahito ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 (4 FLUOROPHENYL)PROPYL ETHER; AROMATIC COMPOUND; BENZENE; CROWN ETHER; ELECTROPHILE; ETHER DERIVATIVE; HYDROXY(PHENYL) LAMBDA3 IODANE 18 CROWN 6 COMPLEX; IODINE DERIVATIVE; IODOSYLBENZENE MONOMER 18 CROWN 6 COMPLEX; UNCLASSIFIED DRUG; [4 (3 METHOXYPROPYL)PHENYL]PHENYL LAMBDA3 IODANE;

ARTICLE; CHEMICAL BOND; CYCLIZATION; FLUORINATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 79952396949     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc10215j     Document Type: Article

References (28)

1. K. Muller, C. Faeh, F. Diederich, Science, 2007, 317, 1881.
2. H.-J. Bohm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Muller, U. Obst-Sander, M. Stahl, ChemBioChem, 2004, 5, 637.
3. M. E. Phelps, Proc. Natl. Acad. Sci. U. S. A., 2000, 97, 9226.
4. E. S. Istvan, J. Deisenhofer, Science, 2001, 292, 1160.
5. J. A. Olsen, D. W. Banner, P. Seiler, U. O. Sander, A. D'Arcy, M. Stihle, K. Muller, F. Diederich, Angew. Chem., Int. Ed., 2003, 42, 2507.
6. J. W. Clader, J. Med. Chem., 2004, 47, 1.
7. T. Furuya, J. E. M. N. Klein, T. Ritter, Synthesis, 2010, 1804.
8. G. I. Borodkin, V. G. Shubin, Russ. Chem. Rev., 2010, 79, 259.
9. S. D. Taylor, C. C. Kotoris, G. Hum, Tetrahedron, 1999, 55, 12431.
10. M. Zupan, in The Chemistry of Functional Groups, Supplement D, ed. S. Patai and Z. Rappoport, Wiley, New York, 1983., ch. 15
11. O. Lerman, Y. Tor, D. Hebel, S. Rozen, J. Org. Chem., 1984, 49, 806.
12. J. Kollonitsch, L. Barash, G. A. Doldouras, J. Am. Chem. Soc., 1970, 92, 7494.
13. S. Stavber, M. Zupan, J. Org. Chem., 1985, 50, 3609.
14. G. S. Lal, G. P. Pez, R. G. Syvret, Chem. Rev., 1996, 96, 1737.
15. V. Grakauskas, J. Org. Chem., 1970, 35, 723.
16. R. E. Banks, J. Fluorine Chem., 1998, 87, 1.
17. T. Umemoto, G. Tomizawa, J. Org. Chem., 1995, 60, 6563.
18. X. Wang, T.-S. Mei, J.-Q. Yu, J. Am. Chem. Soc., 2009, 131, 7520.
19. K. L. Hull, W. Q. Anani, M. S. Sanford, J. Am. Chem. Soc., 2006, 128, 7134.
20. V. Snieckus, F. Beaulieu, K. Mohri, W. Han, C. K. Murphy, F. A. Davis, Tetrahedron Lett., 1994, 35, 3465.
21. M. Ochiai, K. Miyamoto, M. Shiro, T. Ozawa, K. Yamaguchi, J. Am. Chem. Soc., 2003, 125, 13006.
22. M. Ochiai, T. Suefuji, K. Miyamoto, N. Tada, S. Goto, M. Shiro, S. Sakamoto, K. Yamaguchi, J. Am. Chem. Soc., 2003, 125, 769.
23. K. Miyamoto, M. Hirobe, M. Saito, M. Shiro, M. Ochiai, Org. Lett., 2007, 9, 1995.
24. M. Ochiai, in Chemistry of Hypervalent Compounds, ed. K.-y. Akiba, Wiley-VCH, New York, 1999., p. 359.
25. A. McKillop, L. McLaren, R. J. K. Taylor, J. Chem. Soc., Perkin Trans. 1, 1994, 2047.
26. B. Wang, L. Qin, K. D. Neumann, S. Uppaluri, R. L. Cerny, S. G. DiMagno, Org. Lett., 2010, 12, 3352.
27. S. Martin-Santamaria, M. A. Carroll, C. M. Carroll, C. D. Carter, V. W. Pike, H. S. Rzepa, D. A. Widdowson, Chem. Commun., 2000, 649.
28. S. Winstein, E. Allred, R. Heck, R. Glick, Tetrahedron, 1958, 3, 1.