title: Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents.
abstract: A novel type of hypervalent iodine(III) reagents, vinylbenziodoxolones (VBX), has been synthesized in a one-pot reaction from 2-iodobenzoic acid. VBX is bench stable, has been thoroughly characterized and the cyclic structure is supported by X-ray analysis. The reactivity of VBX was investigated in vinylation of nitrocyclohexane, and delivered vinylated products with opposite regioselectivity compared to acyclic vinyl(aryl)iodonium salts. The reagents could become a powerful tool in vinylation reactions under both metal-free and metal-catalyzed conditions.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.
authors.forename: Elin
authors.initials: E
authors.lastname: Stridfeldt
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.
authors.forename: Alexandra
authors.initials: A
authors.lastname: Seemann
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.
authors.forename: Marinus J
authors.initials: MJ
authors.lastname: Bouma
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.
authors.forename: Chandan
authors.initials: C
authors.lastname: Dey
authors.affiliation: Department of Materials and Environmental Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden.
authors.forename: Anne
authors.initials: A
authors.lastname: Ertan
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91, Stockholm, Sweden. berit.olofsson@su.se.
authors.forename: Berit
authors.identifier: http://orcid.org/0000-0001-7975-4582
authors.initials: B
authors.lastname: Olofsson
keywords: benziodoxolones; hypervalent compounds; structure analysis; synthetic methods; vinylation