Metal‐Free Benzylic C−H Amination via Electrochemically Generated Benzylaminosulfonium Ions | Zendy

Hayashi Ryutaro | Zendy; Shimizu Akihiro | Zendy; Song Yetao | Zendy; Ashikari Yosuke | Zendy; Nokami Toshiki | Zendy; Yoshida Junichi | Zendy

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Metal‐Free Benzylic C−H Amination via Electrochemically Generated Benzylaminosulfonium Ions

Author(s) -

Hayashi Ryutaro,

Shimizu Akihiro,

Song Yetao,

Ashikari Yosuke,

Nokami Toshiki,

Yoshida Junichi

Publication year - 2017

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201604484

Subject(s) - amination , chemistry , toluene , electrochemistry , iodide , metal ions in aqueous solution , metal , ion , inorganic chemistry , electrolyte , reductive amination , supporting electrolyte , combinatorial chemistry , organic chemistry , electrode , catalysis

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.

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