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Cathode Material Determines Product Selectivity for Electrochemical C−H Functionalization of Biaryl Ketoximes
Author(s) -
Zhao HuaiBo,
Xu Pin,
Song Jinshuai,
Xu HaiChao
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201809679
Subject(s) - electrosynthesis , chemistry , surface modification , electrochemistry , cathode , anode , bond cleavage , combinatorial chemistry , selectivity , oxime , cathodic protection , oxide , photochemistry , organic chemistry , inorganic chemistry , electrode , catalysis
The synthesis of polycyclic N‐heteroaromatic compounds and their corresponding N‐oxides has been developed through electrochemical C−H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N‐heteroaromatic N‐oxides. The products of the electrosynthesis are switched to the deoxygenated N‐heteroaromatics by employing a Pb cathode through sequential anode‐promoted dehydrogenative cyclization and cathodic cleavage of the N−O bond in the initially formed N‐oxide.