New pyridyl-functionalized organoiron alkynyl complexes. Easy access to polymetallic architectures featuring an electroactive site by simple co-ordination reactions

Journal of Organometallic Chemistry

Volumn 572, Issue 2, 1999, Pages 189-192

  Le Stang, Sylvie ^a   Lenz, Dirk ^a   Paul, Frédéric ^a   Lapinte, Claude ^a  

^a UMR 6509 Organometalliques et Catalyse Chimie et Electrochimie Moleculaires   (France)

Author keywords

Dinuclear complex; Iron acetylide; Organoiron(II); Organoiron(III); Pyridinium salt; Sonogashira coupling; Substituted pyridine

Indexed keywords

STAPHYLOCOCCUS PHAGE 3A;

EID: 0001178291     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)00961-9     Document Type: Article

References (34)

1. Amoroso A.J., Cargill Thompson A.M.W., Maher J.P., McCleverty J.A., Ward M.D. Inorg. Chem. 34:1995;4828.
2. Stang P.J., Olenyuk B. Acc. Chem. Res. 30:1997;502.
3. Huck W.T.S., Roher A., Anilkumar A.T., Fokkens R.H., Nibbering N.M.M., van Vegel F.C.J.M., Reinhoudt D.N. New J. Chem. 2:1998;165.
4. Fujita M., Aoyagi M., Ibukoro F., Ogura K., Yamagochi K. J. Am. Chem. Soc. 120:1998;611.
5. Stang P.J. Chem. Eur. J. 4:1998;19.
6. Le Narvor N., Toupet L., Lapinte C. J. Am. Chem. Soc. 117:1995;7129.
7. Le Narvor N., Lapinte C. Organometallics. 14:1995;634.
8. Guillaume V., Morvan-Mahias V., Lapinte C. J. Organomet. Chem. 554:1998;203.
9. Weyland T., Lapinte C., Frapper G., Calhorda M.J., Halet J.-F., Toupet L. Organometallics. 16:1997;2024.
10. T. Weyland, K. Costuas, A. Mari, J.-F. Halet, C. Lapinte, Organometallics 17 (1998) in press.
11. F. Paul, C. Lapinte, Coord. Chem. Rev., in press.
12. Denis R., Weyland T., Paul F., Lapinte C. J. Organomet. Chem. 545-546:1997;615.
13. Sakanishi S., Bardwell D.A., Couchman S., Jeffery J.C., McCleverty J.A., Ward M.D. J. Organomet. Chem. 528:1997;35.
14. D.E. Ames, D. Bull, C. Takunowa, Synthesis (1981) 364.
15. T. Sakamoto, M. Shiraiwa, Y. Kondo, H. Yamanaka, Synthesis (1983) 312.
16. Della Ciana L., Haim A. J. Heterocycl. Chem. 21:1983;607.
17. Tilley J.W., Zawoiski S. J. Org. Chem. 53:1988;386.
18. Lin J.T., Sun S.-S., Wu J.J., Lee L., Lin K.-J., Huang Y.F. Organometallics. 34:1995;2323.
19. Bunten K.A., Kakkar A.K. J. Mater. Chem. 5:1995;2041.
20. Ziessel R., Suffert J., Youinou M.-T. J. Org. Chem. 61:1996;6535.
21. (a) J.I.-Y. Wu, J.T. Lin, J. Luo, S.-S. Sun, C.-S. Li, K.J. Lin, C. Tsai, C.-C. Hsu, J.-L. Lin, Organometallics 16 (1997) 2038.
22. (b) J.T. Lin, J.J. Wu, C.-S. Li, Y.S. Wen, K.-J. Lin, Organometallics 15 (1996) 5028.
23. M.I. Bruce, M. Ke, P. Low, J. Chem. Soc. Chem. Commun. (1996) 2405-2406.
24. Connors P.J. Jr., Tzalis D., Dunnick A.L., Tor Y. Inorg. Chem. 37:1998;1121.
25. N.G. Connelly, M.P. Gamasa, J. Gimeno, C. Lapinte, E. Lastra, J.P. Maher, N. Le Narvor, A.L. Rieger, P.H. Rieger, J. Chem. Soc. Dalton Trans. (1993) 2775.
26. In a typical coupling reaction, 200 mg of complex 1 (0.325 mmol), 23 mg of bis(triphenylphosphine) dichloropalladium complex (0.032 mmol) and 13 mg of copper iodide (0.065 mmol) were introduced under argon in a Schlenk tube. Subsequently, the halogenoaromatic substrate was introduced in 10 ml of di-iso-propylamine and the mixture was refluxed for 12 h. The solvent was then cryogenically trapped and the brown residue was extracted with toluene and filtered through a celite pad. Evaporation of the toluene and washing with small portions of n-pentane (2×5 ml) at -40°C and acetonitrile (5 ml) yielded the corresponding desired complex 3. The pure compound can be isolated as bright orange powder by recrystallization from a toluene-pentane mixture.
27. R. Denis, F. Paul, C. Lapinte, work in progress.
28. 6] were added to a solution of the corresponding compound 3a-c in 15 ml dichloromethane. Stirring was maintained for 1 h at r.t. and the solution was concentrated in vacuo to ca. 5 ml. Addition of 50 ml of n-pentane allowed precipitation of a solid. Decantation and subsequent washing with 3×3 ml portions of toluene followed by 3×3 ml diethyl ether, drying under vacuum yielded the pure 3a-c+ salt as a dark purple product (87%).
29. 6 were added after 5 h. The reaction mixture is stirred overnight and the solution was concentrated in vacuo. Extraction with dichloromethane and addition of n-pentane allowed precipitation of a dark purple solid. Decantation and subsequent washing with small portions of n-pentane and drying under vacuum yielded the pure 4a salt as a dark purple product (90%).
30. Guillaume V., Thominot P., Coat F., Mari A., Lapinte C. J. Organomet. Chem. 565:1998;75.
31. 6 was sublimed out of the solid residue and the remaining solid was extracted with toluene before being washed several times with small fractions of pentane (-40°C). Drying in vacuo yielded the complex as a deep orange product 5a.
32. F. Paul, S. Le Stang, C. Lapinte, work in progress.
33. Houbrechts S., Clays K., Persoons A., Cadierno V., Gamasa M.P., Gimeno J. Organometallics. 15:1996;5266.
34. R.H. Naulty, M.P. Cifuentes, M.G. Humphrey, S. Houbrechts, C. Boutton, A. Persoons, G.A. Heath, D.C.R. Hockless, B. Luther-Davies, M. Samoc, J. Chem. Soc. Dalton Trans. (1997) 4167.