Literature DB >> 27790762

Metal-Free Benzylic C-H Amination via Electrochemically Generated Benzylaminosulfonium Ions.

Ryutaro Hayashi1, Akihiro Shimizu1, Yetao Song1, Yosuke Ashikari1, Toshiki Nokami1,2, Jun-Ichi Yoshida1.   

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.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H amination; C−H functionalization; benzyl cations; electrochemistry; oxidation

Year:  2016        PMID： 27790762     DOI： 10.1002/chem.201604484

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  8 in total

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