title: Synthesis and structure of bifunctional N-alkylbenzimidazole phenylboronate derivatives.
abstract: N-Methyl and N-n-butyl-2-(2-boronophenyl)benzimidazoles are accessed from the corresponding mono-N-alkyl-ortho-phenylenediamines, either using a polyphosphoric acid-mediated cyclisation with ortho-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 11B NMR and X-ray crystallography.
authors.affiliation: Department of Chemistry, Durham University, Science Laboratories, South Road, Durham, UKDH1 3LE.
authors.forename: Alexandrea J
authors.initials: AJ
authors.lastname: Blatch
authors.forename: Olga V
authors.initials: OV
authors.lastname: Chetina
authors.forename: Judith A K
authors.initials: JA
authors.lastname: Howard
authors.forename: Leonard G F
authors.initials: LG
authors.lastname: Patrick
authors.forename: Christian A
authors.initials: CA
authors.lastname: Smethurst
authors.forename: Andrew
authors.initials: A
authors.lastname: Whiting
mesh_terms: D000478:Alkylation; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D001562:Benzimidazoles; D001897:Boronic Acids; D007202:Indicators and Reagents; C010686:benzeneboronic acid