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Synthesis of novel symmetrical and nonsymmetrical 6-membered heterocycles with pendant electron-rich organoiron substituents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The functionalized complexes [(dppe)Cp*Fe(C≡C)]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(C≡CH)] and the corresponding dibromopyridines using a Sonogashira cross-coupling reaction are also described. By this route, the monofunctionalized products [(dppe)Cp*Fe(C≡C)]-2,6-Py-Br and [(dppe)Cp*Fe(C≡C)]-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(C≡C)]-2,6-Py-[(C≡C)SiMe3] or [(dppe)Cp*Fe(C≡C)]-3,5-Py-[(C≡C)SiMe3] by further coupling.

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Authors
  1. Sylvie le Stang
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  2. Frédéric Paul
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  3. Claude Lapinte
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Additional information

In commemoriation of the centenary of Academician A. N. Nesmeyanov.

UMR CNRS 6509 “Organométalliques et catalyse: Chimie et Electrochimie Moléculaires,” Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1207–1218, September, 1999.

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le Stang, S., Paul, F. & Lapinte, C. Synthesis of novel symmetrical and nonsymmetrical 6-membered heterocycles with pendant electron-rich organoiron substituents. Chem Heterocycl Compd 35, 1063–1074 (1999). https://doi.org/10.1007/BF02251798

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  • DOI: https://doi.org/10.1007/BF02251798

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