Synthesis and structure of bifunctional N-alkylbenzimidazole phenylboronate derivatives

Blatch, A. J.; Chetina, O. V.; Howard, J. A. K.; Patrick, L. G. F.; Smethurst, C. A.; Whiting, A.

Abstract

-Methyl and --butyl-2-(2-boronophenyl)benzimidazoles are accessed from the corresponding mono--alkyl--phenylenediamines, either using a polyphosphoric acid-mediated cyclisation with -bromobenzoic acid, or preferably using an Oxone™-mediated cyclisation of the corresponding aldehyde, followed by a lithium-exchange and borylation sequence. The resulting boronic acids show unusual physical and chemical properties, as shown by B NMR and X-ray crystallography.

Citation

Blatch, A. J., Chetina, O. V., Howard, J. A. K., Patrick, L. G. F., Smethurst, C. A., & Whiting, A. (2006). Synthesis and structure of bifunctional N-alkylbenzimidazole phenylboronate derivatives. Organic and Biomolecular Chemistry, 4(17), 3297-3302. https://doi.org/10.1039/B607127A

• Journal Article Type: Article
• Online Publication Date: Jul 26, 2006
• Publication Date: 2006
• Journal: Organic and Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 4
• Issue: 17
• Pages: 3297-3302
• DOI: https://doi.org/10.1039/B607127A
• Public URL: https://durham-repository.worktribe.com/output/1565973