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Benzimidazole nitrogen-directed, regiocontrolled, lithiation of ferrocenyl- and phenyl-N-n-butylbenzimidazoles

Herault, D.; Aelvoet, K.; Blatch, A.J.; Al-Majid, A.; Smethurst, C.A.; Whiting, A.


D. Herault

K. Aelvoet

A.J. Blatch

A. Al-Majid

C.A. Smethurst


2-Ferrocenyl- and 2-phenyl-N-n-butylbenzimidazoles were synthesized to evaluate the influence of the benzimidazole functional group upon their directed lithiation. The regiochemistry of lithiation was studied, as well as the effect of stabilization of the lithiated species by diamine coordination using tetramethyl- ethylenediamine and (-)-sparteine. The lithiations were followed by reaction with a variety of electrophiles to give the disubstituted 2-ferrocenyl- and 2-phenyl-N-n-butylbenzimidazoles compounds. This study showed that despite a simple n-butyl function on the benzimidazole, directed lithiation was readily achieved with high regiocontrol on the ferrocenyl and phenyl groups. (-)-Sparteine failed to provide asymmetric induction in the ferrocene system, and its inefficiency is explained by intramolecular coordination of the lithiated species by the benzimidazole nitrogen, which is preferred over sparteine coordination.


Herault, D., Aelvoet, K., Blatch, A., Al-Majid, A., Smethurst, C., & Whiting, A. (2007). Benzimidazole nitrogen-directed, regiocontrolled, lithiation of ferrocenyl- and phenyl-N-n-butylbenzimidazoles. Journal of Organic Chemistry, 72(1), 71-75.

Journal Article Type Article
Publication Date Dec 1, 2007
Deposit Date Jan 18, 2008
Journal Journal of Organic Chemistry
Print ISSN 0022-3263
Electronic ISSN 1520-6904
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 72
Issue 1
Pages 71-75