Synthesis of (1-alkynyl)dicarbonylcyclopentadienyliron complexes by palladium-catalyzed Sonogashira-type carbon-iron bond formation

Tetrahedron Letters

Volumn 50, Issue 37, 2009, Pages 5274-5276

  Nakaya, Ryotaro ^a   Yasuda, Shigeo ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; CARBON; COPPER; COPPER IODIDE; DICARBONYLCYCLOPENTADIENYLIRON COMPLEX; DICHLOROBIS(TRIPHENYLPHOSPHINE)PALLADIUM; IODIDE; IRON COMPLEX; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; REACTION ANALYSIS; SONOGASHIRA REACTION; SYNTHESIS;

EID: 67650883238     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.005     Document Type: Article

References (35)

1. Kerber R.C. In: Abel E.W., Stone F.G.A., and Wilkinson G. (Eds). Comprehensive Organometallic Chemistry II Vol. 7, Chapter 2 (1995), Elsevier, Oxford, UK
2. Davison A., and Selegue J.P. J. Am. Chem. Soc. 100 (1978) 7763-7765
3. Davison A., and Solar J.P. J. Organomet. Chem. 155 (1978) C8-C12
4. Medei L., Orian L., Semeikin O.V., Peterleitner M.G., Ustynyuk N.A., Santi S., Durante C., Ricci A., and Lo Sterzo C. Eur. J. Inorg. Chem. (2006) 2582-2597
5. Akita M., and Koike T. Dalton Trans. (2008) 3523-3530
6. Long N.J., and Williams C.K. Angew. Chem., Int. Ed. 42 (2003) 2586-2617
7. Green M.L.H., and Mole T. J. Organomet. Chem. 12 (1968) 404-406
8. Akita M., Terada M., Oyama S., and Moro-oka Y. Organometallics 9 (1990) 816-825
9. Lichtenberger D.L., Renshaw S.K., and Bullock R.M. J. Am. Chem. Soc. 115 (1993) 3276-3285
10. Gamasa M.P., Gimeno J., Lastra E., Lanfranchi M., and Tiripicchio A. J. Organomet. Chem. 405 (1991) 333-345
11. Lo Sterzo C. J. Chem. Soc., Dalton Trans. (1992) 1989-1990
12. Crescenzi R., and Lo Sterzo C. Organometallics 11 (1992) 4301-4305
13. Ricci A., Angelucci F., Bassetti M., and Lo Sterzo C. J. Am. Chem. Soc. 124 (2002) 1060-1071 and references cited therein
14. Lo Sterzo C. Synlett (1999) 1704-1722
15. Selected examples:. Bruce M.I., Humphrey M.G., Matisons J.G., Roy S.K., and Swincer A.G. Aust. J. Chem. 37 (1984) 1955-1961
16. Szesni N., Drexler M., Maurer J., Winter R.F., de Montigny F., Lapinte C., Steffens S., Heck J., Weibert B., and Fischer H. Organometallics 25 (2006) 5774-5787
17. Bruce M.I., Ke M., Low P.J., Skelton B.W., and White A.H. Organometallics 17 (1998) 3539-3549
18. Butler P., Gallagher J.F., and Manning A.R. Inorg. Chem. Commun. 1 (1998) 343-345
19. Bruce M.I., Hall B.C., Low P.J., Smith M.E., Skelton B.W., and White A.H. Inorg. Chim. Acta 300-302 (2000) 633-644
20. Powell C.E., Cifuentes M.P., McDonagh A.M., Hurst S.K., Lucas N.T., Delfs C.D., Stranger R., Humphrey M.G., Houbrechts S., Asselberghs I., Persoons A., and Hockless D.C.R. Inorg. Chim. Acta 352 (2003) 9-18
21. tBuOK provides the corresponding alkynyliron complex efficiently. Connelly N.G., Gamasa M.P., Gimeno J., Lapinte C., Lastra E., Maher J.P., Le Narvor N., Rieger A.L., and Rieger P.H. J. Chem. Soc., Dalton Trans. (1993) 2575-2578
22. Denis R., Toupet L., Paul F., and Lapinte C. Organometallics 19 (2000) 4240-4251
23. Denis R., Weyland T., Paul F., and Lapinte C. J. Organomet. Chem. 545-546 (1997) 615-618
24. Review for the synthesis of alkynylmetal complexes:. Li C.-L., and Liu R.S. Chem. Rev. 100 (2000) 3127-3161
25. See Ref. 3c.
26. Yasuda S., Yorimitsu H., and Oshima K. Organometallics 27 (2008) 4025-4027
27. Asada Y., Yasuda S., Yorimitsu H., and Oshima K. Organometallics 27 (2008) 6050-6052
28. *Fe(dppe)(C{triple bond, long}CH)] with aryl halides were reported. See Refs. 3 and 8.
29. Yasufuku K., and Yamazaki H. Bull. Chem. Soc. Jpn. 45 (1972) 2664
30. 2] (8.8 mg, 0.013 mmol) were placed in a 20-mL reaction flask under argon. THF (1.0 mL), phenylacetylene (82 μL, 0.75 mmol), and diisopropylamine (0.50 mL) were sequentially added at 25 °C. The resulting mixture was stirred for 30 min at the same temperature. The mixture was then passed through a pad of silica gel by using ethyl acetate as an eluent. The filtrate was concentrated in vacuo. Chromatographic purification on silica gel (carbon disulfide/chloroform = 1:1) provided 1a (112 mg, 0.40 mmol) in 81% yield.
31. We believe that purification in a glovebox filled with inert gas would allow isolation of these unstable complexes.
32. The reactions of iodoiron complexes with polyynyllithium were reported:. Sakurai A., Akita M., and Moro-oka Y. Organometallics 18 (1999) 3241-3244 and references cited therein
33. Hay A.S. J. Org. Chem. 27 (1962) 3320-3321
34. Sugiyama J., and Tomita I. Eur. J. Org. Chem. (2007) 4651-4653
35. West K., Wang C., Batsanov A.S., and Bryce M.R. J. Org. Chem. 71 (2006) 8541-8544 and references cited therein