title: Palladium-Catalyzed Oxidative Domino Carbocyclization-Arylation of Bisallenes.
abstract: Herein we report a highly efficient and site-selective palladium-catalyzed oxidative carbocyclization-arylation reaction of bisallenes and arylboronic acids under operationally simple conditions for the selective synthesis of cyclohexadiene derivatives. The palladium source and the solvent proved to be crucial for the selectivity and the reactivity displayed. Interestingly, in the absence of the nucleophile, an oxidative carbocyclization-β-elimination pathway predominates. The reaction conditions are compatible with a wide range of functional groups, and the reaction exhibits broad substrate scope. Furthermore, key information regarding the mechanism was obtained using control experiments and kinetic studies.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University , SE-10691 Stockholm, Sweden.
authors.forename: Chandra M R
authors.initials: CM
authors.lastname: Volla
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University , SE-10691 Stockholm, Sweden.
authors.forename: Jan-E
authors.initials: JE
authors.lastname: Bäckvall
keywords: arylation; bisallenes; carbocyclization; oxidation; palladium catalysis