title: The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling.
abstract: Electrochemical oxidation of toluene derivatives in the presence of a sulfilimine gave benzylaminosulfonium ions as stabilized benzyl cation pools, which reacted with subsequently added aromatic nucleophiles to give the corresponding cross-coupling products. The transformation serves as a powerful metal- and chemical-oxidant-free method for benzylic C-H/aromatic C-H cross-coupling. The method has been successfully applied to synthesis of TP27, an inhibitor of PTPase.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University , Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Ryutaro
authors.initials: R
authors.lastname: Hayashi
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University , Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Shimizu
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University , Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Jun-Ichi
authors.initials: J
authors.lastname: Yoshida
mesh_terms: D001554:Benzene / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D002244:Carbon; D006859:Hydrogen; D001554:Benzene