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

Abstract

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.

Keywords

• triarylmethanes
• nucleophilic aromatic substitution
• 4-picoline/4-methylpyridine
• 4-fluorobenzonitrile