title: Metal-Free Benzylic C-H Amination via Electrochemically Generated Benzylaminosulfonium Ions.
abstract: Electrochemical oxidation of toluene derivatives in the presence of N-tosyldiphenylsulfilimine gave the corresponding benzylaminosulfonium ions, which were treated with tetrabutylammonium iodide under non-electrolytic conditions to give N-tosylbenzylamines. The transformation serves as a metal- and chemical-oxidant-free method for benzylic C-H amination. Because of high oxidation potential of N-tosyldiphenylsulfilimine the present method can be applied to synthesis of various benzylamines from functionalized toluene derivatives.
authors: Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Ryutaro
authors: R
authors: Hayashi
authors: Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Akihiro
authors: A
authors: Shimizu
authors: Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Yetao
authors: Y
authors: Song
authors: Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Yosuke
authors: Y
authors: Ashikari
authors: Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.|Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Koyamachominami, 680-8552, Tottori, Japan.
authors: Toshiki
authors: T
authors: Nokami
authors: Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
authors: Jun-Ichi
authors: JI
authors: Yoshida
keywords: C−H amination; C−H functionalization; benzyl cations; electrochemistry; oxidation