Cathode Material Determines Product Selectivity for Electrochemical C−H Functionalization of Biaryl Ketoximes. (22nd October 2018)

• Record Type: Journal Article
• Authors: Zhao, Huai‐Bo; Xu, Pin; Song, Jinshuai; Xu, Hai‐Chao
• Is Part Of: Angewandte Chemie. Volume 130:Number 46(2018)
• Page Start: 15373
• Page End: 15376
• Publication Date: 2018-10-22
• Subjects: C-H-Funktionalisierung -- Gekoppelte Elektrolyse -- Heterocyclen -- Oxime -- Radikale; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201809679
• Languages: English
• ISSNs: 0044-8249

Abstract

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.