SYNTHESIS OF NOVEL SYMMETRICAL AND NONSYMMETRICAL 6-MEMBERED HETEROCYCLES WITH PENDANT ELECTRON-RICH ORGANOIRON SUBSTITUENTS

Авторы

  • Sylvie le Stang Editorial Office "Chemistry of Heterocyclic Compounds"
  • Frédéric Paul UMR CNRS 6509 "Organométalliques et catalyse: Chimie et Electrochimie Moléculaires," Université de Rennes
  • Claude Lapinte UMR CNRS 6509 "Organométalliques et catalyse: Chimie et Electrochimie Moléculaires," Université de Rennes

DOI:

https://doi.org/10.1007/763

Аннотация

The functionalized complexes [(dppe)Cp*Fe(CºC)]2–(Py)(Py = 2,6-C5H3N and 3,5-C5H3N (dppe = 1,2-bis(diphenylphosphino)ethane) were isolated in good yields from reaction of the chloro complex (dppe)Cp*FeCl with the protected bis-acetylenic heterocyclic precursor. These electron-rich pyridyl ligands constitute interesting examples of organometallic heterocycles bearing redox-active substituents. Attempts to find an alternative route starting from the alkynyl complex [(dppe)Cp*Fe(CºCH)] and the corresponding dibromopyridines using a Sonogashira cross-coupling reaction are also described. By this route, the monofunctionalized products [(dppe)Cp*Fe(CºC)]-2,6-Py-Br and [(dppe)Cp*Fe(CºC)]-3,5-Py-Br could be cleanly isolated. These compounds open the way to the generation of heteroaromatics featuring nonequivalent alkyne substituents such as [(dppe)Cp*Fe(CºC)]-2,6-Py-[(CºC)SiMe3] or [(dppe)Cp*Fe(CºC)]-3,5-Py-[(CºC)SiMe3] by further coupling.

Also published in Chemistry of Heterocyclic Compounds, 1999, 35 (9), pp 1063-1074

http://link.springer.com/article/10.1007/BF02251798

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Опубликован

2013-06-26

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Оригинальные статьи