D. Herault
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.
Authors
K. Aelvoet
Dr Alex Probert alex.probert@durham.ac.uk
Biophysical Sciences Institutes Manager
A. Al-Majid
C. A. Smethurst
Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor
Abstract
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.
Citation
Herault, D., Aelvoet, K., Blatch, A. J., Al-Majid, A., Smethurst, C. A., & Whiting, A. (2007). Benzimidazole Nitrogen-Directed, Regiocontrolled, Lithiation of Ferrocenyl- and Phenyl-N-n-butylbenzimidazoles. Journal of Organic Chemistry, 72(1), 71-75. https://doi.org/10.1021/jo061639%2B
Journal Article Type | Article |
---|---|
Online Publication Date | Dec 7, 2006 |
Publication Date | Jan 5, 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 |
DOI | https://doi.org/10.1021/jo061639%2B |
Public URL | https://durham-repository.worktribe.com/output/1535404 |
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