title: Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade.
abstract: A practical synthesis of fused benzimidazoles 5 has been developed by simply heating o-halonitrobenzenes 1 with tetrahydroisoquinolines 2. In this transformation, 2 played multiple roles as a building block, base and a double hydride donor in a cascade of uncatalyzed aromatic substitution, reduction of the nitro group, oxidation of the α-methylene group and condensation.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France. nguyen@icsn.cnrs-gif.fr.
authors.forename: T B
authors.initials: TB
authors.lastname: Nguyen
authors.forename: L
authors.initials: L
authors.lastname: Ermolenko
authors.forename: A
authors.initials: A
authors.lastname: Al-Mourabit