Ortho-lithiation of N-aryl ferrocenylmethanimines

[Display omitted] •N-aryl ferrocenylmethanimines were lithiated at ortho-position of ferrocene with BuLi.•Addition of various electrophiles (ketones, RHal) led to 1,2-disubstituted ferrocenes.•N-aryl-ferroceno[c]pyrrol-2-ium triflates formed after cyclization of ketone addition products with Tf2O. A...

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Published in:Inorganica Chimica Acta 2019-09, Vol.495, p.118976, Article 118976
Main Authors: Nikovskiy, Igor A., Spiridonov, Kirill A., Zakharova, Daria V., Platonova, Elena O., Pavlov, Alexander A., Nelyubina, Yulia V., Polezhaev, Alexander V.
Format: Article
Language:English
Subjects:
Aromatic compounds
Carbenes
Ferrocene
Ferrocenes
Halides
NHC precursors
Ortho metalation
Ortho-lithiation
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Summary:[Display omitted] •N-aryl ferrocenylmethanimines were lithiated at ortho-position of ferrocene with BuLi.•Addition of various electrophiles (ketones, RHal) led to 1,2-disubstituted ferrocenes.•N-aryl-ferroceno[c]pyrrol-2-ium triflates formed after cyclization of ketone addition products with Tf2O. A series of N-aryl ferrocenylmethanimines was successfully lithiated at ortho-position with the following treatment with various electrophiles such as ketone, alkyl and silyl halides yielding 1,2-disubstituted ferrocenes with good yields. The product of benzophenone addition was characterized with X-ray diffraction study. We showed that cyclization of 2-hydroxymethylferrocenylcarbimines with Tf2O led to formation of 5H-pyrrolo[3,4-a]ferrocen-6-ium salt - a potential precursor of ferrocene-based heterocyclic carbenes.
ISSN:0020-1693
1873-3255
DOI:10.1016/j.ica.2019.118976