4,4’-(Pyridin-4-ylmethylene)dibenzonitrile

This communication describes an unprecedented substitution cascade, in which 4-methylpyridine, following deprotonation with LDA, twice acts as a carbon nucleophile in an unusual SNAr process, to form a novel triarylmethane structure. A proposed mechanism for this sequence is presented that is suppor...

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Bibliographic Details
Published inMolBank Vol. 2021; no. 4; p. M1302
Main Authors Lancaster, Ben M. J., Nicholls, Alexander J., Baxendale, Ian R.
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.12.2021
Subjects
4-fluorobenzonitrile
4-picoline/4-methylpyridine
Catalysis
Chromatography
Nitrogen
Nucleophiles
nucleophilic aromatic substitution
Single crystals
triarylmethanes
X ray analysis
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Summary:This communication describes an unprecedented substitution cascade, in which 4-methylpyridine, following deprotonation with LDA, twice acts as a carbon nucleophile in an unusual SNAr process, to form a novel triarylmethane structure. A proposed mechanism for this sequence is presented that is supported by single crystal X-ray analysis of the resulting product. We believe this unique transformation is of note as it highlights a neat and efficient entry as a single step to complex triarylmethane architectures containing both substituted phenyl and pyridyl aromatics.
ISSN:1422-8599
1422-8599
DOI:10.3390/M1302