A new route to polykis(dialkylamino)benzenes and -naphthalenes based on protodefluorination of electron-rich fluoroaromatics: Anion radicals of arenes as a simple and effective alternative to 'classical' LAH-based systems

Synthesis

Volumn , Issue 1, 2006, Pages 97-102

  Sorokin, Vladimir Igorevich ^a   Ozeryanskii, Valery Anatolievich ^a   Borodkin, Gennady Sergeevich ^a  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

Aromatic anion radicals; Electron transfer; Fluorinated amino arenes; Lithium aluminum hydride; Protodefluorination

Indexed keywords

AROMATIC COMPOUNDS; FLUORINE; HYDRIDES; LITHIUM COMPOUNDS; NAPHTHALENE;

AROMATIC ANION RADICALS; ELECTRON TRANSFER; FLUORINATED AMINO ARENE; LITHIUM ALUMINUM HYDRIDE; PROTODEFLUORINATION;

BENZENE;

ALUMINUM DERIVATIVE; ALUMINUM LITHIUM HYDRIDE; ANION; AROMATIC COMPOUND; BENZENE DERIVATIVE; FLUORINE DERIVATIVE; FLUOROBENZENE; LITHIUM DERIVATIVE; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; RADICAL; REDUCING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DEFLUORINATION; ELECTRON TRANSPORT; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 30944435032     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921755     Document Type: Article

References (23)

1. Smith, M. B.; March, J. March's Advanced Organic Chemistry; John Wiley & Sons: New York, 2001, 22-24.
2. Krespan, C. G. In Chemistry of Organic Fluorine Compounds II: A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; American Chemical Society: Washington, 1995, 297-300.
3. Kuhl, S.; Schneider, R.; Fort, Y. Adv. Synth. Catal. 2003, 545, 341.
4. Sorokin, V. I.; Ozeryanskii, V. A.; Borodkin, G. S. J. Fluorine Chem. 2005, in press.
5. Sorokin, V. I.; Ozeryanskii, V. A.; Pozharskii, A. F. Eur. J. Org. Chem. 2004, 766.
6. (a) Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527.
7. (b) Ito, A.; Ono, Y.; Tanaka, K. J. Org. Chem. 1999, 64, 8236.
8. Aleksandrovskii, Y. A.; Bezhikina, L. V.; Rodionov, Y. V. Biokhimia (Moscow) 1981, 46, 708.
9. Christensen, J. B.; Schiødt, N.-C.; Bechgaard, K.; Buch-Rasmussen, T. Acta Chem. Scand. 1996, 50, 1013.
10. (a) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
11. (b) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041.
12. Seyden-Penne, J. Reduction by the Alumino- and Borohydrides in Organic Synthesis; Wiley-VCH: New York, 1997, 224.
13. Staab, H. A.; Elbl-Weiser, K.; Krieger, C. Eur. J. Org. Chem. 2000, 327.
14. Stewart, J. J. P. MOPAC 6.0 Quantum Chemistry Program Exchange, University of Indiana, Bloomington, Indiana, USA.
15. Imamoto, T.; Takeyama, T.; Kusumoto, T. Chem. Lett. 1985, 1491.
16. Fuchibe, K.; Akiyama, T. Synlett 2004, 1282.
17. Everett, S. In Chemistry of Organic Fluorine Compounds II: A Critical Review; Hudlicky, M.; Pavlath, A. E., Eds.; American Chemical Society: Washington, 1995, 1037-1086.
18. Wang, H. C.; Levin, G.; Szwarc, M. J. Am. Chem. Soc. 1978, 700, 3969.
19. Rembaum, A.; Eisenberg, A.; Haack, R.; Landel, R. F. J. Am. Chem. Soc. 1967, 89, 1062.
20. Arnett, E. M.; Ko, H. C.; Chao, C. C. J. Am. Chem. Soc. 1972, 94, 4776.
21. Beletskaya, I. P.; Bessmertnykh, A. G.; Guilard, R. Tetrahedron Lett. 1999, 40, 6393.
22. Takeda, N.; Imamoto, T. Org. Synth. 1998, 76, 228.
23. Schröder, U.; Wadhawan, J.; Evans, R. G.; Compton, R. G.; Wood, B.; Walton, D. J.; France, R. R.; Marken, F.; Page, P. C. B.; Hayman, C. M. J. Phys. Chem. B 2002, 106, 8697.