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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.