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Cathode Material Determines Product Selectivity for Electrochemical C-H Functionalization of Biaryl Ketoximes
Huai-Bo Zhao1, Pin Xu1, Jinshuai Song2
1State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P. R. China.
Abstract:
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.
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