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Synthesis 2000; 2000(10): 1421-1426
DOI: 10.1055/s-2000-7117
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High Yield Synthesis of 2-Substituted (N,N-Dimethylaminomethyl)ferrocenes

Sophie Picart-Goetgheluck* , Olivier Delacroix, Lucien Maciejewski, Jacques Brocard
  • *Groupe de Synthèse Organométallique, Laboratoire de Catalyse, UPRESA 8010, ENSCL, Cité Scientifique, BP 108, F-59652 Villeneuve d'Ascq Cedex, France; Fax + 33(3)20 43 65 85; E-mail: Sophie.Goetgheluck@ensc-lille.fr
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Publication Date:
31 December 2000 (online)

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An improved synthesis of 2-(N,N-dimethylaminomethyl)ferrocenecarboxaldehyde (2) by ortho-lithiation and formylation of N,N-dimethylferrocenylmethylamine (1) has been carried out. A wide range of reaction parameters (nature and amount of RLi, addition of t-BuOK, solvent, reaction time and temperature) have been varied. The best set of reaction conditions allows to reach a 94% yield. Other functionalized products have been synthesized following this new procedure using various electrophiles.

amines - aldehydes - diastereoselectivity - N,N-dimethylaminomethylferrocene - hydrogen transfer - ortho-lithiation - iron - organometallic reagents